Sideshow Bob vs Count Olaf (The Simpsons vs A Series of Unfortunate Events)

 

"To defeat an enemy, you must know them. Not simply their battle tactics, but their history, philosophy, art."

- Grand Admiral Thrawn

Sideshow Bob, the silent assistant turned maniacal mastermind hunting Bart Simpson Count Olaf, the despicable arsonist forcing the Baudelaires through a Series of Unfortunate Events

To children, the world can be a scary place, with many strangers willing to take advantage of them. And no one quite represents that danger over these two. While they initially seemed to be simple thespians, they had grand ambitions that they were willing to stoop to criminal methods to reach, and when some children managed to stop their plots, they’d dedicate themselves to a vendetta where they’d ensure these children’s lives would be a neverending hell at their hands, with many complicated schemes, manipulative tactics, and impressive disguises utilized to achieve this goal. So, if these two maniacal miscreants met and tested their mettles, which performer of arts both theatrical and deadly would make this the other’s final curtain?

Before We Begin

I’d like to give a quick note here to establish what this blog will be discussing. For Bob, while The Simpsons does have a weird relationship regarding continuity, there is still a pretty clear dividing line between what is and isn’t canon. As such, Bob will be taking from all of his canon episode appearances, which means he’s barred from equipment and feats from his appearance in non-canon episode material such as Treehouse of Horror or couch gags, as well as from certain supplementary material that is also non-canon like the games and the Universal Studios ride. This will also include details from the various Simpsons comic runs, which are a bit harder to lock down in terms of their canonicity, but I’ve gone through his appearances in them on a case by case basis, and any details included here are from stories that I feel have no real reason to declare them to be non canon. 

As for Olaf, this will be compositing him between information from all the versions of A Series of Unfortunate Events, including the original book series and other novels set in the same universe, the 2004 movie and its various video game adaptations, and the 2017 Netflix series. That being said, the source material does take precedence, and as such, any elements of later stories that are outright contradictory to the original book series will not be included. Though Daniel Handler, the IRL author of the books, also worked as an executive producer and writer on the Netflix series, so I personally feel additions that version made to the world of the series can be seen as validly canon as well. Also, there do be full spoilers here, so be wary. 

Background

Sideshow Bob

“Hello, Bart.”

“AHHH! SIDESHOW BOB!”

Robert Underdunk Terwilliger Jr. is a classically trained man with abnormally large feet who had dreams of making it big. Unbeknownst to him, his first big break would instead be accidental, as his accompaniment to one of his brother Cecil’s auditions led to him accidentally gaining the role of an assistant to children’s entertainer Krusty the Clown, who had found his quiet indignity in reaction to a pie to the face to be a perfect foil to his zaniness. Now under the stage name Sideshow Bob, he initially seemed to take to his new role well, but he secretly resented Krusty due to his increasing cruelty to him on camera, as well as learning the clown had done various illicit actions off the set. Fed up with this, he’d end up disguising himself as Krusty and framed him for the armed robbery of the Kwik-E-Mart, which led to Krusty Getting Busted, and Bob to take over his show and make it far more intellectually stimulating to the children of the nation. However, his plot would wind up unraveled by a young boy named Bart Simpson, who exposed Bob’s plotting and led to his arrest, though not before Bob declared that he would gain his revenge against Bart.

While within prison, he would wind up meeting and dating a woman on the outside, and after he had served his time, he’d wind up proposing to her. But in an odd twist of fate, this woman would be Bart’s aunt, Selma Bouvier, and after he realized she was a fan of MacGuyver, a show he personally despised deeply, he’d instead attempt to kill Selma for her inheritance in a gas explosion, which was thankfully stopped thanks to Bart’s quick deductions. This furthered Bob’s growing grudge on the boy, and after being paroled from prison, he would begin harassing Bart via various threats to kill him, putting Bart into a Cape of Feare and forcing the Simpsons into witness protection. Bob would pursue them, and after gaining a second lifelong rivalry in rakes, he’d trap Bart on a houseboat in an attempt to end him. Bart was able to prevent his death by baiting Bob into singing the entirety of the HMS Pinafore as a last request, which delayed Bob for long enough for the boat to run aground and to get arrested again. 

He’d make various other attempts on Bart’s life, among them including a plot where he rigged an election to become Mayor of Springfield, an attempt to get the town to abolish television under threat of an atomic bomb, and a plot by his brother to flood Springfield with an exploding dam, which Bob was still arrested for despite the fact he was innocent to that plot. In his next plot, he had learned Krusty had agreed to erase Bob from all older recordings of their show, which aggravated Bob enough to plot to kill Krusty at his upcoming retirement performance. He’d end up hypnotizing Bart into becoming a manchurian candidate which would kill Krusty in a suicide bombing. However, a Krusty that was regretful over the two’s falling out would make a dedication song to Bob at the performance, which touched Bob enough to call off the bombing, and seemingly patched up the bad blood between the former colleagues. Bob would later be pulled out of prison to help protect Bart’s dad Homer after a few attempts on his life. After uncovering the culprit of these, being the son of Homer’s unknown Enemy Frank Grimes, he’d corner Bart and attempt to kill him simply with no complicated scheme, but he had found that he had grown accustomed to Bart's face, and instead ran off into the night. 

After this, Bob would flee the country, and would attempt to get a fresh start in Italy. While he initially had issues adapting, his large feet made him the perfect grape crusher for the country’s wine trade, which gave him local acclaim, eventually leading to him becoming the mayor of the small town of Salsiccia and marrying his wife, Francesca, who he would have a son with by the name of Gino. However, due to being on a misadventure to deliver a Lamborghini to Mr Burns, the Simpsons would end up stumbling into the town, much to their mutual shock. They initially tried to part peacefully, but a drunk Lisa would end up spilling the beans on Bob’s past, leading to the town shunning him. In response, Bob declared a vendetta against the entire family, and would attempt to kill them as they fled the country, aided by his wife and son. Later, after returning to the states, he’d attempt to kill them in a fake barbeque restaurant with an exploding laptop, though this plan was seemingly thwarted when Bob activated the bomb on himself to prove he didn’t misquote Shakespeare. In the ensuing trial, Bob’s father would suggest that Bob’s insanity had been egged on by Bart, which managed to turn the town against him. This only got worse after Bart tossing away some medicine he thought was a bomb led to Bob seemingly dying of a heart disease. However, when Bart was alone at the later Funeral for this Fiend, he would find out that Bob had faked his death in an attempt to kill Bart in the funeral home’s cremation chamber with the help of his entire family. However, the rest of the Simpsons stopped it, leading to the entire Tellwinger family being arrested and promptly getting forgotten about in future episodes.

His next attempt on Bart’s life would come with the announcement that minor offenders from the Springfield Prison would be released due to budget cuts. Taking advantage of this, he drugged up his cellmate Walt Warren and performed a painful face swapping surgery himself. He’d use this new identity to move in as a neighbor to the Simpsons, before kidnapping Bart. He intended to take Bart to a location where 5 state borders met, and kill him in such a way that it would be unprosecutable due to no one part of the act taking place in one state’s border (which would just make the crime the jurisdiction of a federal court btw). However, some interference from Walt and quick thinking from Bart would lead to this plot being once again thwarted. Later, after getting his face back, he’d end up a test subject at a GMO Food corporation for community service, which ended up enabling him to become the Chief Scientist of the company. During a family visit, Lisa would end up befriending Bob, due to their shared interest in the fine arts and sciences. However, on a visit to a museum, she’d find out that Bob had used his position in order to modify his own genes to give him various superhuman abilities. After being provoked by Bart, he’d attempt to kill both children by tossing them from the top of a dam, but Lisa managed to talk some reason into him, leading to him realizing the monster he’d become and attempting to take his own life by plunging off the dam. He’d end up surviving because he forgot he gave himself gills. After returning to prison, Bob would end up learning that Bart had gone missing and was presumed dead, which he refused to accept, breaking out of prison to try and track down this Gone Boy. He’d end up finding that Bart was trapped in an abandoned missile silo, and would strap Bart to the rocket in an attempt to kill him once and for all. However, a call to his prison therapist would end up convincing him to not go through with it, eventually leading to him returning to jail. He later escaped jail to do stuff as a mall santa, but that really wasn’t a good episode so I won’t talk about it.

He made many other attempts on Bart’s life throughout the years in other media, his methods always shifting, but his goal always clear. However, his never ending failure to kill a boy ultimately seemed to waver his confidence, despite his slipping mental state. One potential future showed the ultimate result of this, as he had grown into an old recluse working in a lighthouse, giving younger men the advice that life was short and to not waste their lives on a quest for revenge. Regardless of if that’s his destiny or if it’s just to die to a rake smacking him in a bar, Sideshow Bob’s quest for revenge is as neverending as his show’s lifespan. No matter how many times Bart stops his plots, Sideshow Bob will always come back with another one, just as twisted as the last. 

Count Olaf

“Your first impression of me may be that I am a terrible person. But in time, Baudelaires, I hope you'll come to realize... you haven't the faintest idea.”

When you first clicked on this page and saw his name at the top, you may have been mistakenly thinking I’d be discussing a snowman created by an ice princess or some such whimsical fairy tale. I am sorry to say, this blog will be discussing someone far more unpleasant. If you wish to see something whimsical like that snowman instead, I’d advise leaving this page and looking elsewhere for something to read and dissect the capabilities for harm they have. This story, on the other hand, begins with a fire and a broken family. One day, the three children of the wealthy Baudilere family, that being the inventive eldest daughter Violet, the studious son Klaus, and biting obsessed youngest daughter Sunny, while on a pleasant trip to the beach, were informed of an unfortunate event: their parents had been killed in a mysterious house fire which engulfed their mansion. Now orphaned, the children were whisked away to their closest living relative (a word which here refers to the closest geographically, not closest in terms of blood relation), a “world renowned” theater actor by the name of Count Olaf. While Olaf played nice to the other adults which concerned themselves with the Baudelaires, the orphans quickly discovered his true colors: He was an evil man, who forced the orphans into squalid conditions and made them complete round the clock chores. His true goal was to gain the Baudilere’s inherited fortune by marrying Violet, by way of casting her as his bride in a play about a wedding which would technically be valid as an actual wedding due to casting an actual judge as the officiator of the play’s wedding. Thankfully, the orphans did manage to stop this plot via a legal loophole involving Violet signing the marriage certificate with her non-dominant hand, and exposed his criminal intentions in the process. However, Olaf managed to flee the authorities, and as he did this, he made a chilling promise to Violet: He would stop at nothing to gain the fortune of the siblings, and then murder them with his bare hands. 

Not much is known for sure of Olaf’s origins. There’s some implication that he had been enrolled in Wade Academy or starred in a film about zombies in the snow, but those aren’t conclusive enough to say for sure. What we do know is that at a young age, he was abducted and made a member of the Volunteer Fire Department, or VFD, which is a massive secret organization dedicated to keeping the peace from the shadows, putting out the figurative fires of the world. Olaf did demonstrate some troubling signs of his future as a youth, such as reveling in killing ants with a magnifying glass and writing obscene words into anagrams, but he’d be a skilled agent into his adulthood, even finding love in a woman named Kit Snicket. However, one fateful night at the opera ended up pushing him into villainy. During a scuffle where Kit’s brother Lemony and a woman named Beatrice would attempt to claim a fairly important sugar bowl, Olaf’s father would wind up victim to a poisoned dart in the crossfire, making Olaf an orphan himself. This made Olaf slip into villainy, leading to him playing a role in causing a massive schism in the VFD between the ones fighting fires and the ones who thought it more appealing to start them, and inspired a lifetime vendetta against the woman he felt ended his family, which eventually bled into her three children after she died in a mysterious house fire. 

After his initial plot was thwarted, the Baudileres would end up in the care of many other more legitimate guardians, as the VFD secretly tried to keep them safe from the shadows. Olaf, however, would chase after them, accompanied with his acting troupe and donning many different disguises to kill many of those guardians, as well as agents sent to stop him. These included him posing as an assistant to the herpetologist Dr Montgomery Montgomery before murdering him, seducing their Aunt Josephine as a sea captain before leaving her for dead in a lake full of leeches, and posing as the Secretary to an optometrist at a lumber mill, who would end up hypnotizing Klaus into causing a deadly accident. After these unfortunate events, a phrase which here means series of scenarios that were far from optimal and is also a sneaky reference to the name of the series, the Baudileres would end up at a fancy boarding school, where they met another group of rich children orphaned by a mysterious fire in the Quagmires. The Quagmires would end up learning quite a bit about the VFD. However, before they could share this with the Baudelaires, Olaf, while posing as the school’s gym coach, kidnapped them for their own inherited fortune. The kids would next end up in the care of a rich financial advisor named Esmé Squalor, and they’d find out Olaf was attempting to smuggle the Quagmires out of the city due to a massive manhunt for him. However, it turned out Esmé had fallen in love with Olaf and intended to help him with his plot, and with the help of both a literal and figurative red herring, they escaped with the Quagmires. 

Next, the Baudilares would end up in the care of a village of people obsessed with rules and crows, which Esmé and Olaf infiltrated by posing as police officers. They’d end up arresting a VFD agent by the name of Jacques Snicket, and promptly made him look like Olaf, which the villagers promptly intended to execute via burning at the stake. The Baudilares would see through the frame up and attempt to break Jacques out of jail, but Olaf would personally murder Jacques, and used their jail break plans to frame them for his murder. After the Baudilares managed to escape jail, they’d also rescue the Quagmires from Olaf’s clutches, though the groups were forced apart as the Quagmires went up in an air balloon while the Baudileres fled, now branded fugitives. Olaf would next follow the orphans to a hospital, at which he intended to skip the fortune gathering and just kill the orphans by performing a decapitation on Violet under the guise of surgery. After this fails, he sets fire to the hospital and flees, unaware that the orphans had managed to sneak into the trunk of his car and follow him to his next location, a run down carnival. At this, he’d consult with the carnival’s psychic, Madame Lulu, who would inform him that a survivor of a fire was alive in the mountains, which he and the orphans take to mean one of the Baudelaire parents had survived. During this, the orphans would end up disguising themselves amidst the carnival’s freak show, only to learn that Olaf had convinced Lulu to kill one of the freaks by feeding them to lions to drive up publicity. During this lion show, Lulu would end up dead due to secretly being a VFD agent by the name of Olivia Caliban, and as he burned the carnival and allied himself with the rest of the freaks, he’d reveal he had seen through the Baudilare’s disguises and sent the eldest pair to their potential deaths in a runaway caravan trailer as he kidnapped Sunny. 

The Baudileres thankfully managed to survive, and would end up meeting with a group of Snow Scouts, which featured a bratty girl named Carmelita Spats and a mysterious boy who turned out to be an up-to-then-assumed dead brother of the Quagmires, whom was the survivor of the fire in the above instance. While this happened, Olaf would force Sunny to do some demeaning chores before he was approached by a Woman With Hair But No Beard and a Man With a Beard But No Hair, who were veteran VFD members who intimidated even Olaf with their presence, and intended to expand their organization by any means necessary. The two plots would end up coinciding as the two veterans would kidnap the rest of the Snow Scouts with a net and many eagles, Esmé would end up adopting Carmelita due to recognising her potential for evil, and the Baudelaires end up tumbling into an ocean. During this, Olaf ended up having lost several of his minions due to death, and he’d end up losing more due to him commanding them to toss a baby off a cliff. The Baudilares would next end up at sea and would get caught up in a submarine that had a girl named Fiona on board, which was looking for a mysterious and important Sugar Bowl that was kind of floating around, a phrase which here can refer can refer to the fact it had been weaving in and out of the narrative as a MacGuffin, or that it was literally floating around in the water. The children would end up venturing into an underwater grotto that the bowl may have washed up on. They did not find a bowl, but they did find some very deadly mushroom spores which were quarantined within the grotto, and which Sunny winds up accidentally carrying a sample outside. While they do manage to save Sunny, they find that the crew of the sub had been captured by Olaf and his remaining associates in a far larger and more intimidating submarine. The orphans would end up captured by Olaf himself, but they manage to escape thanks to Fiona being the long lost sister to Olaf’s last remaining original associate, a man with hooks for hands, and talked him into betraying his master. 

After this, the Baudileres would end up in a hotel that acted as the last safe haven for VFD agents, at which they would pose as the concierges. The hotel was also where the Sugar Bowl had been secreted away to, which led to Olaf making an ultimate plan to get his hands on it. The hotel had also been a gathering ground for the various adults the kids had encountered on their long, unfortunate journey, who were there to form a trial to finally bring Olaf and his associates to justice. During his plot to gain the Bowl, Olaf would end up threatening a man named Dewey who ran a VFD archive under the hotel with a harpoon gun, but when the Baudelaires end up confronting him, he ends up hesitating and hints he secretly regrets the lengths he’s gone to, he simply believes he’s incapable of doing anything else. Olaf disarms himself of the harpoon gun, but the Baudelaires end up accidentally dropping the gun, which discharges and kills Dewey. Olaf is then dragged away to face trial in the commotion.

The next day during the trial, due to a literal taking of the phrase “justice is blind” to mean that everyone present ought to be blindfolded, Olaf is able to rig his trial into one for the Baudelaires thanks to the judges being the aforementioned Man & Woman With One Beard And One Hair Between Them. After verbally assaulting the crowd, calling them out for being so incompetent as to allow him to get away with his plans, he’d end up finding the Sugar Bowl was not in the hotel, and then he would promptly attempt to use the deadly spores to kill everyone in the building, which the orphans accompany him on due to wanting to stop him and not trusting any of the adults in the building due to their continued incompetence. He sets the building ablaze on Sunny’s suggestion, and as they escape, many of the people inside the hotel have their fates up in the air, including Esmé and Carmalita, who Olaf had grown sick of. Only once he gets to the roof does he realize that his impulsive arson also led to him inadvertently signaling to any remaining VFD agents that their supposed safe haven was compromised, which would lead to him taking a sailboat out to sea with the orphans and the unreleased spores. 

Olaf would spend their voyage gloating over how he had seemingly triumphed, but after a storm, the group would end up marooned on an island. Olaf would attempt to name the island after himself, only to be cast out by islanders living on it due to his ego. Then, after unsuccessfully attempting to disguise himself as the now also marooned and also pregnant Kit Snicket, he’d end up trapped in a bird cage. This essentially caused reality to crash down on him, with his usual plans and tactics not working, and he’d end up sympathizing with the orphans, telling them life is unfair, and indirectly denying he had been the one to cause the fire that started these unfortunate events, though the wording does make this hard to believe. Olaf would make one final gambit, as the leader of the islanders fired his confiscated harpoon gun at his stomach, which also unleashed the deadly spores from the diving helmet he had kept them in and used as a fake pregnant belly, though the harpoon would still travel far enough to fatally wound him. After this, Olaf would end up solemnly awaiting his death, having realized all his plotting and evil had brought him nothing in the end aside from a harpoon in the gut. He’d then learn that his long lost love Kit was in labor, and with some hesitation, he’d use the last of his energy to do the one selfless act of his life: Carry Kit from the raft of books she was stuck on to the beach of the island where she would better be able to give birth to her daughter. After this, he’d lay down next to her, and he’d leave the Baudelaires with some parting words quoted from Phillip Larkin. After this and one last unsettling laugh, Olaf’s life would end. While the orphans had suffered greatly at his hands, they couldn’t help but feel some sorrow towards his end, and after Kit’s own life ended after giving birth, the two would be buried on the island, together in death. Then the Baudilares took a ship and sailed off to their uncertain futures, Count Olaf having left an irrevocable mark on them, in a manner not too dissimilar to the burns on someone barely escaping a house fire. 

Intelligence & Skill

Sideshow Bob

Sideshow Bob is an exceptionally intelligent mastermind. He has a doctorate in an unknown field from Yale, and has a vast knowledge on various fine arts and literature. He memorized the HMS Pinafore well enough to do an impromptu one man performance of it, is fluent in multiple languages, and has good knowledge of the works of Shakespeare thanks to his mother being a prominent performer of it. His intellect isn’t just limited to the arts, as he was able to rise to the chief scientist of Monsanto Inc, a GMO Food Corporation, at which he made 5000 patents, as well as knowing how to modify his own genes. He also knows how to fly the Wright Brothers plane, and was able to hack into and control a Willy Wonka-esque factory run by Krusty from a laptop in prison in an attempt to kill Bart.

His intelligence lies in areas beyond just academics, of course. While his criminal plans are often thwarted, he has managed to pull off many impressive feats in pulling them. He framed Krusty to take over his show, tried to kill Selma via a gas leak, rigged an election by counting dead people as voters, snuck around a military base to steal a nuclear warhead, and created a school for criminals that was able to turn the bullies into successful criminals.

He’s also a pretty skilled manipulator. He managed to talk himself into parole despite clearly showing violent intent, managed to do a convincing enough campaign that he likely would have won the mayoral election legitimately had he not cheated, and was able to talk a group of protestors still upset he tried to nuke them into giving him a second chance. 

He’s also a very talented singer.

Count Olaf

While both live action versions have him be a more comical villain, Olaf in the original material is a serious and sinister threat. He was an agent of the VFD in the past, and he’s clearly learned a lot from his time there. He easily manages to outsmart most of the adults around him, often fooling them with disguises and escaping capture. And this wasn’t just restricted to gullible adults, as he takes heavy advantage of the fact that other VFD agents and even the narrator himself seem to underestimate his intelligence, leading to him constantly outwitting them, even successfully murdering many of them. And even though the Baudelaires are often the only ones to see through his disguises, he still manages to outwit them quite a bit, to the point where Violet herself was scared of him and thought of him as “an unsavory, clever drunken brute”. Even in his more comical live action depictions, he’s seen not getting fooled by certain tricks that his literary counterpart fell for, as in the movie he catches on to Violet’s attempt to sign the marriage certificate with the wrong hand, and in the Netflix series he saw through the Baudilare’s freak disguises, which he needed Madame Lulu’s help to see through in the books.

He’s shown good skill in manipulation of people. He was able to talk Georgina Orwell into working with him despite the fact he had tried to murder her earlier in their lives, convinced a village that the Baudilares were murderers, talked a portion of a crowd of people that were at a trial for him into seeing the Baudelaires as just as guilty, and he used reverse psychology to get Esmé and Carmelita to go directly towards the source of a fire he started, leading to their potential deaths.

Also he’s a very talented singer.

Equipment

Sideshow Bob

Knife

His main weapon of choice, which he’s used a variety of times in attempts to stab Bart. He’s used various types, ranging from kitchen knives, a combat knife, and a pen knife, but they all get the job done.

Pistol

Another weapon he’s used in a few variations. He used a basic handgun to aid in his framing of Krusty, used a revolver to threaten the family in his fake barbeque plan, before going back to the handgun for his plot to kill Bart between state lines. All of them presumably shoot bullets like guns are known to do.

Disguises/Costumes

As a performer, Bob has naturally put on many faces throughout his time. In terms of disguises made specifically to hide his identity, there’s his Krusty outfit that he used to frame the clown, Wes Doobner, the western owner of a fake family barbeque place, and Walt Warren, a man whose face he stole. In terms of other outfits, he’s dressed up as various cast members of the HMS Pinafore, an opera clown, and Santa. Given he was able to dress up as the Pinafore guys with no preparation, it’s likely that could apply to all the others. 

Announcement Van

Used in Cape Feare, in which he drove about the Simpson’s neighborhood to assure everyone that he was not going to murder anyone besides Bart. Though he also didn’t mention Rod & Todd, so I guess he was probably planning to kill them eventually too.

Machete

Used in Cape Feare to try and kill Bart in the climax, possibly as a homage to Jason Voorhees to fit the episode being a whole plot reference to horror classic “Camp Fear”. He’s also recently been seen using one to try and swipe at Bart in the opening theme.

Ropes

From Cape Feare, Bob had used this to restrain the rest of the family before trying to kill Bart uninterrupted. He probably didn’t need to tie up Snowball, because cats definitely do not give a fuck if their owners are in danger.

Sword

Also from Cape Feare, Bob had pulled this sword out of seemingly nowhere to match his Captain costume, before he tried to finish Bart off after finishing his last request. It is presumably not a prop, as Bart was probably about to find out.

Plastic Explosives

In Day of the Jacknapes, Bob’s plan was to try and kill Krusty by rigging up a hypnotized Bart to explode when hugging Krusty. Genius, as it would be taking out two of his three nemesis in one blast, assuming there were no rakes nearby. Bob is directly shown making them himself, and this batch of bombs was later shown to be powerful enough to destroy a room and blow a door off its hinges.

Motorcycle

In The Italian Bob, the Simpsons are fleeing from the Italian town after accidentally ruining his life, leading to him chasing them down in this while on a Roman aqueduct. Reddit users identified the bike to be a Ducati 999.

Trash Poker

In Gone Boy, he is seen using one of these for the intended use of picking up garbage on the side of the road. It is presumably sharp enough that if he stabbed an actual person it would hurt a bit.

Scissors

Also in Gone Boy, Bob was handed a pair of one of these by his therapist, attempting to give him the inspiration to figuratively cut Bart out of his life by literally cutting a picture of him. Bob instead decided to cut a vein in his leg non-figuratively.

Speargun

In Bobby, It’s Cold Outside, Bob used this to threaten two men he thought were after him for legal reasons. Turns out they just wanted him to be a Christmas Village Santa. Presumably has a wide range, given he used it to threaten people from the top of a lighthouse, and when he shot it upwards he killed a bird that was flying overhead. It also looks similar to the speargun he used to kill Bart the first time in the only good section of the non canon Treehouse Of Horror XXVI.

Lever Action Rifle, Mace, Baseball Bat

Seen in an umbrella stand inside Bob’s lighthouse in Bobby, It’s Cold Outside. Presumably not for decoration.

Axe

I’m actually not sure if he’s ever used this in an episode, but this is apparently an official render of him wielding one, so you can probably toss this into his arsenal somewhere.

Hacksaw

After an issue of being cuffed by the ankle to Bart, Bob went to a hardware store and grabbed one of these with the intention of freeing himself from Bart in order to be able to kill him without needing to drag a corpse everywhere. Fortunately for Bart, he managed to stop Bob before he could recreate what people in handcuffs usually do with hacksaws.

Strychnine

After Bart thwarted Bob’s plan to kidnap Mr Burns in an ambulance, Bob attempted to use this to make sure if he was going down, he’d take Bart with him. Though I have no idea why something usually used for rat poisons would be lying around in an ambulance in the first place.

Hypnosis Flute

After studying snake charming, human physiology, and sound reproduction, Bob created a flute that enabled him to hypnotize Bart over the phone.Upon hearing the flute, Bart would be placed under a spell, and would act normally and under his own control until a trigger was hit, making him go back under the spell and follow Bob’s command. Bob used it to make Bart literally eat his shorts, play with girls and embarrass himself at recess, and make Bart play in traffic (though Bart was able to workaround the danger of it by emptying a honey truck before the trigger hit). However, the flute can be countered by playing a counter medley, which made the flute break and Bob be the one to be put under a spell instead.

Count Olaf

Knife

First seen in The Reptile Room, and becomes Olaf's go-to weapon for threatening the children. It’s sharp and stabs things. He’s also demonstrated proficiency in throwing it. 

Harpoon Gun

His main ranged weapon, it’s first seen in the Vile Village, where it’s used by Esme to cut off the Baudelaire's escape by rope ladder, which killed a crow in the process. Olaf later uses it to try and murder Dewey Denouement, and while he does back down, the Baudilares accidentally drop it and cause it to kill him anyways. He’d use it to take Justice Strauss as a hostage in his escape from the hotel and into the boat, only to later ironically die to it after it’s confiscated. It’s been portrayed both in a realistic long rifle-like form and in a more compact pistol-like form.

Various Finery Disguises

Count Olaf’s most notable equipment would be his various disguises, which he used to, well, disguise his identity to the various adults he encountered. The various personas he’s undertaken include the foreign assistant Stephano, the seafaring Captain Julio Sham, Shirley the receptionist, the school coach Genghis, the foreign auctioneer Gunther, the “famous” detective Dupin, and the unseen HR director Mattathias. In the Netflix series, he also utilized the disguises of a bartender, a doctor, a ringmaster, and a tourist dad. In The Carnivorous Carnival, it’s revealed that these all came from a kit full of various disguises, which was standard issue for VFD Agents to help them fool enemies of the organization. The full contents of this kit are listed here.  

Spyglass

Another standard issue VFD item. In the original books, there isn’t too much to them, and in the film, they’re just used as a right of passage object given to VFD members, but in the Netflix series, their role is expanded into being essentially decoder swiss army knives. It has several navigational tools on the outside, like a compass and barometer, and by turning the dials on it in certain ways, the spyglass can switch into a variety of other functions. There are 2,016,125 possible configurations, but from what we’ve seen, the spy glasses can look at things from far away, like you’d expect one too, decipher coded text it looks at, turn into a flashlight, and send out a beam of concentrated heat/light that can start fires, though the beams aren’t hot enough to do something like melt metal. They’re also heavy enough to be used as improvised clubs, should the need arise.

Car

Count Olaf’s vehicle of choice for getting around and fleeing crime scenes. Originally it was depicted as a very old classic car. In the movie, it was portrayed as a custom made 1960 Chrysler Imperial Crown Limousine, while in the Netflix series, it was portrayed as a 1968/1969 Oldsmobile Toronado.

Walkie Talkie

Used many times, Olaf communicates and coordinates with his various minions with these. The receivers are able to be hidden amidst ordinary clothes, for more conspicuous communication.

Lighter

Being a part of the fire starting side of the schism in VFD, Olaf is naturally pretty good at starting fires, which he uses this to aid in. 

Poisoned Darts

Seen in the Netflix series, he used it to kill Dr Montgomery’s former assistant, Gustav, to give a plausible cover story in order for Olaf to portray his replacement assistant. The poison was fairly fast acting, giving Gutav just a couple seconds to give a warning over radio before dying.

Venom Injector

Used in The Reptile Room, it is a double barrel syringe that he used to kill Dr Montgomery by injecting him with venom in such a way that it would look like he was bitten by an incredibly deadly viper or some other dangerous reptile. Originally it was just a single needle, but the Netflix series made it cooler.

Machete

Seen in the Netflix series, which Olaf first used to threaten Jacquelyn when she confronted him on a boat to Peru. He’s not seen using it to ever attack people though.

Speedboat

In the film version, Olaf pilots a personal speedboat to rescue the Baudelaires from the leeches in the lake. It probably goes pretty fast

Sword

Also seen in the film, Olaf uses this sword to cut off the head of a mannequin in a play. It’s not totally clear if the sword is a prop or not, but the sound effect does imply it was.

Cake

In the PC version of the game, the ending mostly follows the beats of the film’s versions of events up until Klaus burns the marriage license. At that point, Olaf yells a bit at the crowd who’s booing him, before Violet ends up leaving the stage and he starts repeatedly pelting her with slices of wedding cake. Yes, this is the actual final boss. No, I don’t know why.

Cane Sword

Used in The Ersatz Elevator, and part of the VFD disguise kit, this is a jeweled cane with a retractable blade on the end. He used this to try and kill Jerome Squalor by cutting a chandelier while demonstrating a party trick, and later to demonstrate that the VFD the orphans bought at an auction was not their friends. It was also used by Georgina Orwell before her unfortunate death by saw blade/fire, which in the book, she used to have a brief sword vs teeth fight with Sunny which was sadly absent from the Netflix adaptation.

Red Herring Statue

Used in The Ersatz Elevator, to smuggle the Quagmires out of the city in an auction. The fish is hollow inside, and the red herring on the outside is ironic since the more figurative red herring in the scenario was a set of Very Fine Doilies which Olaf tricked the orphans into thinking was where the triplets really were located.

Crowbar

Used in the Vile Village, to murder Jacques Snicket by beating him to death offscreen. In the original books, Jacques’ cause of death was unknown. He also later uses it to murder some perfectly innocent hospital lights.

Medical Tools

Used in The Hostile Hospital, where while posing as a doctor, Olaf gained various medical tools which are capable of harming as much as healing, which he would demonstrate by giving Violet a cranioectomy, or in less fancy words, decapitation. These tools included a scalpel, bone saw, skull drill, large knife, and an anesthesia gas machine, which lets him knock people out. 

Starving Lions

Seen in The Carnivorous Carnival, these were once trained by VFD, and would roam the Hinterlands, looking for food. Olaf would capture two that he did intend to feed, though it was with an innocent Madame Lulu and a less innocent Bald Man. So it might have been a net good deed?

Whip

Used in The Carnivorous Carnival, to “train” the above-mentioned lions, and also intimidate the crowd because he was reckless in it. Esmé also has a whip known as tagliatelle grande, which is a comically large wet noodle for some reason.

Caravan

Used in The Carnivorous Carnival, this was a carriage that was part of the carnival. In the books, it’s where the Freaks lived, while in the Netflix series, it’s a gift shop. At the end, as they are driving over a cliffside, Olaf cuts the rope holding it to his car in order to send it careening off a cliff to Violet & Klaus’ deaths, which set up a literal cliffhanger ending.

Medusoid Mycelium

First seen in The Grim Grotto, this is a deadly species of mushroom which releases spores that will kill anyone who inhales them within an hour, growing thickly and rapidly inside their throat until they choke to death. The growth process on the mushrooms themselves is also incredibly rapid, meaning once unleashed it will grow widely around wherever is dark and damp, making it potentially very devastating. It was originally grown to combat the evil side of VFD, only to be quarantined within a grotto deep below the ocean after other members feared it could lead to a worldwide epidemic. However, a sample of it ended up within the diving helmet of Sunny, nearly killing her. Olaf then took the helmet for himself, initially with the intention of releasing it on a hotel full of his enemies, though he was forced to flee before he could. He’d later end up using it as a last ditch effort to take control of a tribe of islanders he encountered while marooned on an island, getting a harpoon in the gut that also inadvertently unleashed the spores on the island. The only known cure for the spores is to eat something with a strong bitter taste or intensity, which has been shown to include horseradish, wasabi, Eutrema, and wormwood. There’s also a unique crossbred food of an apple and a horseradish which is said to immunize anyone who eats to the effects, and Olaf did eat it, though that was minutes before his death so it’s unlikely he’d have access to it for the sake of VS.

The Beatrice/Carmelita II/Olaf 

First seen in The Penultimate Peril. This small sailboat was initially built for the Baudilare’s parents, which they used to get off a deserted island they were on. Olaf at some point gained it via unknown methods, which his temporary adopted daughter would name after herself. He’d use it to escape from the fire of Hotel Denouncement with the Baudelaires in tow, renaming it after himself in the process. They’d end up marooning on ironically the same island the boat was originally built to sail away from, and after the end of their tale, the Baudilares would use it to sail away from the island to their unknown futures. It sure is a boat.

Abilities & Skills

Sideshow Bob

Stealth

Aside from his various disguises, Bob has demonstrated fairly good skill hiding himself in a more literal sense, in stealth. He’s managed to sneak his way out of prison multiple times, snuck around an air force base to hijack multiple military vehicles and steal a deactivated atomic bomb, and has managed to get the drop on Bart several times thanks to this. He escaped from a crashed jet and into a separate vehicle faster than the guards were able to reach him, and snuck across American borders by hiding amidst some illegal Canadian immigrants.

Acrobatics/Agility

His circus training has enabled him to be very acrobatic. As seen above, he’s capable of doing 6 backflips and a frontflip in a row. He’s also rather flexible due to his time in Cirque Du Soleil, as he’s able to stretch himself far enough to hit both ends of a missile launch console. Finally, he’s a skilled contortionist, able to fit himself into a small box.

Vocal Mimicry 

While he already has the voice of an angel for singing, he’s able to disguise his one voice fairly well. He made a convincing impression of Krusty while disguised as him, and after only hearing a few lines from him, he made a good enough impression of an air force colonel to convince other soldiers on the base.

Hypnotism 

Bob has demonstrated several different methods of hypnosis through the years. There’s the above mentioned flute, but he’s also used a spiral to hypnotize Bart into trying to kill Krusty, which Bart seemed completely blind to the effects of. In a more elaborate example, Bob used subliminal messaging from a hypnotist to slowly brainwash the town into acting like him and trying to kill Bart. Though this was more gradual and needed a second party in the form of the Hypnotist to pull off.

Gene Spliced Abilities

After becoming the head scientist of Monsanto Inc, a GMO food corporation, Bob used his position to genetically modify his own genes with various superhuman powers. The abilities he’s shown off include:

• Carrot to solve his presbyopia, suggesting his vision’s enhanced.

• The strength of a Brahma bull, which enhanced his own strength to far greater levels (see feat segment for specific examples).

• Corn for hair highlights, which will be very important to any fights he’s in for sure.

• Zombie Ant Fungus, which makes him go into a murderous rage at the slightest provocation, such as a lady being annoying about pictures he was taking.

• Grasshopper Thighs, enabling him to jump much higher than a normal human.

• Sonar of a Killer Whale, meaning he’d likely be able to track you down very easily.

• The detachable jaw of a Python, which I’m going to hope means he isn’t capable of vore.

• Chicken wings, which he used to briefly fly.

• Gills, which he used to breathe underwater.

It’s worth noting that it is somewhat questionable if he still has access to these abilities, as he currently has not used them outside of the episode he gained them in. However, it’s also not been explicitly stated if he lost the powers or not, so I feel it’s most likely fair game.

Count Olaf

VFD Training

Children taken in by the VFD end up going through a rigorous amount of training, becoming very skilled in a variety of fields at a young age. Olaf’s infamous ankle tattoo is actually a common way agents identify each other, though Olaf and other evildoers being open about them has led to the remaining good folk being a lot cagier about them. Some of the topics the training goes over includes:

• Fire-Fighting, which as the name of the organization implies, was what the group was originally founded to do only to expand. This means recruits are given a lot of training on what arson is, witness burnt buildings, and learn proper fire fighting techniques. Though the training can easily be taken to inadvertently give them lessons on how to commit arson, which was likely Olaf’s main takeaway.

• Literature, which involves a lot of studying up on various classic literature and poetry, as the organization believed being well read meant they’d be well off. While Olaf does balk several times at the idea of literature, his final words being a direct quote from a poet indicate he wasn’t totally tuned out of this.

• Coding, which involves the study of various encoding methods to aid in covertly informing others of information, including their own original method in the Sebald Code. Olaf was particularly interested in anagrams, as even into adulthood he used them a lot to create aliases for himself and his associates.

• Sneaking, which covered the art of hiding in plain sight. The final exam for this involves the instructor entering a small cabin, with a floor covered in glass figurines, in the middle of a leafy woods and sitting blindfolded in a chair, after which students were instructed to get the drop on him by midnight to pass.

• Disguise Training, which is likely where his aptitude for disguising himself came from (see elsewhere for more details).

• Theatrics, which involves learning how to convey coded messages in melodramatic dialogue, and could be the origin of his love of the stage.

• Poison Recognition Training making them able to determine if a poison had been added to cheese fondue without even tasting it

• Archery Training to be precise to the point of hitting an olive with a bow and arrow.

• Eavesdropping, to help them covertly learn information

• Mountain-Climbing and/or Cave-Exploration Training

• Athletics

• Fencing

• Mapmaking

• Dancing

• Rhetorics

• Philosophy and Smoked Fish

After graduating from these classes, a recruit still needs to work under a chosen chaperone to work as their apprentice, with each of them offering specialized training in the field, including ballooning, submarining, and investigative detective work. After the chaperone is satisfied with their progress, they become fully fledged agents in the field. That said, it is unknown who Olaf worked as the apprentice for, though given what we know of him, it likely involved some sort of stagecraft.

(Questionably) Master Actor

Olaf has claimed he is the world’s greatest actor, and while that was likely a boast for his ego, as his actual stage acting leaves a lot to be desired, he is fairly skilled at his craft in other ways. His disguises are able to fool everyone except for the children, even when against Poe, who has personally interacted with all of them. He’s good at shifting his voice to match each role, and in the Netflix series, he’s able to improvise convincing disguises without the use of his kit, and is so good that a facial recognition machine specifically programmed to scan for him couldn’t identify him. 

Hypnotism 

In The Miserable Mill, Olaf teams up with the optometrist Georgina Orwell, whose optometrist appointments were actually a method for her to hypnotize people. She’d end up hypnotizing Klaus into unwillingly causing various accidents in the hopes of getting him kicked off the property, culminating in him almost cutting the mill’s assistant and possible boyfriend in half. In the Netflix series, she had also hypnotized the entire workforce of the mill into being complacent workers who didn’t care about their conditions, something that was merely implied in the original books. Her hypnotism was shown to take effect through various flashing images, and implant trigger words on the target. If they hear a trigger word, they will be compelled to obey whatever the people who said it said with no resistance, and the trance will last until they hear the end phrase, which will send them out of the trance with no memory of actions done during it. Though in the books the process would need to be repeated in order to re-trance them. While this was mainly done by Orwell, she did compile her methods into a book, and the narration mentions Olaf had also read up on said book, meaning he could likely do the same methods if given the chance.

Possible 4th Wall Awareness

In the Netflix series, Olaf has several comments that lean on the 4th wall. This includes him mentioning he was on a TV show in the city for 9 years, in reference to his actor’s time on the sitcom How I Met Your Mother, him being unsure exactly how much time has passed at the end of Season 1, saying it's either a year, a week, or a season, and most blatantly, having a couple comments on his preference for streaming shows and dislike of Nickelodeon films, directly looking into the camera in the process. There’s also several advertisements where he directly speaks to the audience, and the main theme song seems to be sung from his perspective and features shifting voices to match his disguise in each episode. There’s also ads for the film where he speaks to the audience, though since they are advertisements the canonicity of them is fairly questionable.

Stage Magic

(man the guy in this unrelated gif looks familiar for some reason)

In the Netflix series, Olaf briefly demonstrates some knowledge of stage magic, doing the classic “pull object from inside someone’s ear” and “scarf that’s actually a bunch of scarves tied together” tricks. He also pulls a bird out of nowhere, which unfortunately was dead. This was added likely because his actor, Neil Patrick Harris, is a trained magician himself who likes to show that off in his roles.

Associates

Sideshow Bob

The Terwilliger Family

While they haven’t really shown up in canon much after Funeral for a Fiend, that episode is based around them assisting Bob’s latest scheme. While they are last seen in prison, there’s no reason to assume they couldn’t have broken out of prison offscreen like Bob does, meaning I feel it’s fair to include them potentially coming in to help. They consist of:

• Cecil Terwilliger, Bob’s brother, is his most recurring family member. Though he’s also the one who’s had the most strained relationship with Bob. Due to Bob’s preferential treatment by his parents, Cecil had been filled with resentment for his older brother, which only deepened after Bob unwittingly upstaged him and received Cecil’s dream role as Krusty’s assistant. He’d end up going into hydroelectric work, forming his own company. After one of Bob’s releases from prison, Cecil offered him a job as the supervisor of the construction of the Springfield Dam. However, the dam was actually a front for him to launder money, and his ultimate goal was to kill Bob in the destruction of the dam, framing him for the flooding of Springfield in the process. Ultimately Bob and Bart thwarted his plans, though Bob was arrested alongside his brother despite not being a part of the plan. He seemingly patched things up with Bob in prison, as he’d later assist in the plot to kill Bart after Bob faked his death, which he helped with by manipulating Bart into going to Bob alone with some seemingly wise words. He also had a stint in the comics where he ended up trying to kill Lisa, in a rivalry that made both of them feel not as overshadowed by their brothers. He’s an intelligent guy, having become the head of a company thanks to a 4 year degree at Princeton (or clown college, as Bob called it), and he has the resources to get bombs and other weapons. He’s also a lot more pragmatic than Bob, given he was willing to kill Bart just by tossing him off a dam instead of doing something more theatrical.

• He also may have had a son with an unknown wife, since the comics introduce Bob’s nephew Neil Terwilliger, and it’s not been mentioned if the two have had any other siblings. However, Neil himself likely wouldn’t be a part of a family outing like this, as he was making an active effort to dissociate with his criminal uncle.

• Francesca Terwilliger is Bob’s wife from Italy. She had fallen in love with him without knowledge of Bob’s past, and had a son with him, and while she did initially feel betrayed by Bob lying when the truth came out, she ultimately decided to stay loyal to her husband and joined in on his vendetta on the Simpsons. Though, after she and the rest of Bob’s family were forgotten about, Bob was seen being interested in other women, and makes no mention of his son even when asked if he had kids, implying either they got divorced offscreen or Bob is cheating on her. Or the writers just forgot she existed, which, you know, given the other things they’ve retconned, isn’t too unbelievable.

• Gino Terwilliger, Bob’s son. Unlike his mother, he seemed perfectly fine with being related to an attempted murderer, though maybe a bit too into the idea, given how gleefully he wields a knife to kill the enemies of his papa. Though given he is a toddler, it’s unclear how useful he’d be overall. Also he’s older than Maggie somehow, because I guess she’s just cursed to be a baby forever. 

• Robert Terwilliger Sr, Bob’s father. During the fake death plot, Robert manipulated Bob’s trial by insinuating that Bart was the one actively pushing Bart into insanity, before covertly injecting Bob with a drug that would simulate death by putting him in a temporary coma. He’s a doctor who can likely provide other drugs to Bob if needed, though given his actor is dead, he’s likely not making another appearance anytime soon.

• Judith Terwilliger, Bob’s mother, is a retired Shakespeare actor. She doesn’t really do anything beyond that, though she was introduced with “dame”, implying she was knighted at some point.

• Sideshow Bobby, a British cousin of Bob. Given he is a constable in a different country, he probably wouldn’t help the family. I just thought the fact he exists is funny and wanted to bring it up.

Count Olaf

The Acting Troupe

Count Olaf’s fellow actors, who also act as his henchpeople in his plots. Much like Olaf himself, while the Netflix adaptation would make them more comical and incompetent, in the original books they are generally as intelligent and evil as him. Notably, while Olaf’s disguises were often immediately picked through by the Baudelaires, the other’s disguises would be more foolproof. Their members consist of:

• The Hook-Handed Man, real name Fernald, is Olaf’s right hand man, having pirate hooks for hands (or marginally more practical hook-shaped prosthetics in the Netflix series), and was the minion who stayed by Olaf’s side the longest. He’s also a former VFD agent himself, following in the footsteps of his father, Captain Widdershins. After an arson on Anwhistle Aquatics with his step-father, during which it’s implied he lost his hands, he’d end up developing a cynical take on the world after he was credited as the sole perpetrator. He’d end up falling in with Olaf’s troops, and would stay with him until he ran into his sister in The Grim Grotto, who ultimately encouraged him to betray Olaf, which he did.

• The Bald Man with a Long Nose is the big guy, who’s a very rude and aggressive man and second only to Olaf himself in terms of evil. In the books, he stays loyal to Olaf until his death, in which he ends up accidentally pushed into the lion pit with Madame Lulu and gets eaten by lions. He’s also a recurring miniboss in the game, during which he uses snake charming and tosses around an anchor. 

• The White/Powdered Faced Women who are twin sisters that were born as conjoined triplets, though their third sister died under a mysterious fire. They’re loyal to Olaf mainly because they’re in love with him, and bicker with each other for his attention. However, Olaf commanding them to toss Sunny off a cliff, possibly along with suspicion that he may have something to do with their sister’s death, led to them abandoning him.

• The Henchperson That Looks Like Neither a Man Nor a Woman, or the Henchperson of Indeterminate Gender if you feel less loquacious, who was probably the one most changed in the translation to live action. In the book, they’re a hulking fat person who never talks and is framed as a frightening presence, and near constantly referred to as “it”. Needless to say, a little awkward in hindsight given modern standards regarding non-binary stuff, hence why their appearance in live action were with normal people who were simply androgynous. Also in the books, they potentially die in the Heimlich Hospital fire.

• The Wart-Faced Man is the guy that turned out the lights in the theater to help Olaf escape in the first book, before he promptly disappears from the rest of the series with no explanation. Ironically, he was also described as important looking. He may have been retroactively combined with the Bald Man, but it’s not clear.

• 4 other actors who also disappeared without explanation after the first book, consisting of a woman with very short hair and 3 short men. They didn’t even have the courtesy to do anything of note before leaving.

Esmé Squalor

First seen in The Ersatz Elevator, Esmé initially seemed like a well meaning adult adopting the children, being the city’s sixth most important financial advisor and obsessed about what is and isn’t in and trendy with fashion. However, it turned out she had fallen in love with Olaf, who had also been an acting coach for her in the past, and after pushing the orphans down an elevator shaft, she’d become an ally of his, essentially becoming the second most prominent antagonist under Olaf himself. She’s also a former VFD agent, and can be just as cruel as Olaf. However, her obsession with staying fashionably trendy has also led to her making questionable choices, such as smoking even though she hates the taste of cigars, abandoning dinner reservations on a whim, choosing to start a life of crime even though she’s already fairly wealthy, and putting on impractically gaudy outfits when she’s supposed to be keeping a low profile. This, alongside her obsession to locate a Sugar Bowl, ultimately led to Olaf abandoning her in a hotel fire, which may have killed her.

The Carnival Freaks

In The Carnivorous Carnival, Olaf ends up posing as the ringmaster of a carnival with several freaks2` as part of a Freak Show there, and he manages to prey on their insecurity and want to be accepted in order to bring them into his fold. While they did have an uncertain doom after intending to leave him in the Netflix series, in the original books, they stick by Olaf up until his fleeing of the hotel. They consist of Hugo the hunchback, Colette the Contortionist, and Kevin, who is a normal guy that just happens to be ambidextrous. 

Carmelita Spats

Originally an annoying brat first seen in The Austere Academy, Carmelita is a very loud and full of herself girl that loves calling people she doesn’t like cakesniffers, especially if they are orphans. She’d end up coming back in The Slippery Slope, leading a group of other rich kids on a Snow Scout trip. She’d end up encountering Olaf and Esmé, and after realizing she was like mindedly cruel, Esmé promptly adopted her. She loves singing and dancing, though she’s so bad at it Violet and Klaus mention feeling they were tortured by it, and she did once shoot down a crow mid flight. That being said, she’s so annoying that Olaf had no problems abandoning her to her potential death, which I sincerely hope did happen because she fucking sucks. 

Feats

Sideshow Bob

Overall

• Has almost killed Bart Simpson many times.

• Has a doctorate from Yale in an unknown field.

• Escaped prison and talked his way into parole many times.

• Became mayor of a town twice.

• Won an Emmy Award for “Best Supporting Actor in Children’s Program”.

• Has defeated The Simpsons, Chief Wiggum, Frank Grimes Jr, & Milhouse.

• Has fucked twice.

• Stole the theme to Camp Fear as his own leitmotif.

Power

• Able to harm Bart Simpson regularly

• Regular weight lifter

• Sliced into part of a metal bar with machete

• Punched hole in a door window

• Carried Bart & Lisa one armed

• Held up weight of himself and Homer while hanging on the bottom of a blimp

• Carried Bart one armed

• Tossed Bart overhead into coffin by knife that was snagged in his shirt

• Overpowered Homer & Chief Wiggum offscreen (if you’re wondering it’s from a montage of photos from the end of Chief of Hearts)

• Overpowered & lifted Milhouse one armed 

• Had to be restrained with chains and at least 8 weightlifter weights 

• Knocked out priest in one hit with wooden plank 

• Dug tunnels out of prison on his own 

• While under effects of the gene splicing:

• Caught a falling steel sculpture and tossed it away 

• Casually broke a chain and kicked a block of concrete out of a skylight 

• Tossed large marble sculpture hard enough to damage wall

• Tossed around Jimbo & Dolph, overpowered Kearney 

• Should compare to other Simpsons strength feats, including

• Homer dueled a guy while using motorcycles as melee weapons, lifted a large boulder, casually carried 85 pounds of cotton candy, and punched through a crowd of people to save Mark Hammil.

• Marge managed to pull Homer, Bart, & Lisa into their cellar while fighting hurricane force winds.

• Skinner knocked out two men in a single move each, before tossing a briefcase hard enough to knock out a third.

• Willie overpowered an Alaskan Timber Wolf that was stronger than Bart.

• Homer has knocked down Bender with a broom strike, and he has supported the weight of the Planet Express ship, vibrated hard enough to shake a house, and was rocketed out of earth’s orbit before surviving orbital reentry.

Speed

• Casually dodged various objects tossed at him in prison riot

• Got out of a crashed jet and into another plane faster than he could be intercepted 

• Rode Ducati fast enough to catch up with a Lamborghini 

• Reacted to rifle gunfire by pushing up back end of a dump truck to block the bullets 

• Regularly chases after Bart, who can run fast enough to appear as a blur and dodge bullets fired by the Rich Texan. This by extension should also allow him to scale to other Simpsons speed feats.

• Lenny can throw a punch at 100 miles per hour

• Homer has dodged a cannonball (174.58 m/s), dodged most of the bullets from police as Pie Man, and dodged bullets from mobsters 

• Krusty has dodged bullets fired by mobsters on two different occasions 

• Abe Simpson dodged a beam of light in his sleep. 

• The Simpsons can scale to the Planet Express crew, who can pilot the Planet Express Ship, which is fast enough to go to the edge of the universe in a short time frame. 

Durability

• Blasted by cannonfire 

• Got a hammer to the foot 

• Blood loss from using his blood as a pen

• While strapped to the bottom of a car, endured speed bumps to the back of the head, coffee getting poured on his face, and getting driven through a cacti field

• Smacked in face by many rakes 

• Trampled by marching band & several elephants

• Fell off cliff into water

• Crashed very slow plane into shack

• Fell from about halfway up water dam onto a metal pipe near the bottom crotch first 

• Clubbed with Tom Clancy books to the point of bruising, and had various books thrown at him 

• In storage locker as it was fumigated 

• Violently electrocuted by shock bracelet multiple times, once to the point of smoke being emitted from his body 

• Was in an offscreen violent car crash caused by Homer 

• Mentions he was able to write haikus while being beaten with soap 

• Intentionally allowed laptop to explode in his lap

• Run over by a train

• Inside a washing machine and dryer as they were running

• Survived his face being ripped off on five different occasions

• Electrocuted to the point where his hair was set on fire

• While under the effects of the gene splicing, fell from top of Springfield Dam into water below, slamming into the dam several times in the process.

• Run over by truck of rakes 

• Kicked by Homer up stairs and out second story window while in a box

• Dragged on the ground alongside train

• Survived a car crash that launched him through a billboard and off a cliff in the past, and later fell into a cart full of barbed wire

• Smashed in the face with a bus seat

• Was in cell that got crashed into by a jet 

• Shocked with defibrillators, though he was incapacitated for long enough to be restrained

• Run over by Duff Beer truck, though he was hospitalized afterwords 

• Should compare to other notable Simpsons durability feats, including:

• Bart regularly survives being choked by Homer

• The entire Simpsons family shocked each other with enough energy to start flickering lights in nearby buildings.

• Homer, Bart, and Milhouse survived being in close proximity to a toy rocket exploding.

• Bart & Homer sprayed each other with Buzz Cola, which was shown to be acidic enough to melt metal and burn a hole in Bart’s stomach.

• Homer survived falling  down Springfield Gorge twice, getting struck by lightning presumably 50 times, and being in a garage that was full of exploding fireworks, twice.

• Principal Skinner has walked through a raging river and bulldozed through a bridge without reacting, along with being in close proximity to his car exploding from a grenade launcher.

• The Flanders survived their house being violently demolished in a hurricane

• Bart survived being at the epicenter of a sonic blast that shattered most of the glass in a wide area of Springfield.

• Chief Wiggum survived being in a tank that exploded. (0.095 tons of TNT) 

• Homer grabbed a beer can that exploded hard enough to blow the roof off the Simpsons house, which Bart was also close to (0.15-0.39 tons of tnt) 

• Frank Grimes was in a silo that exploded, though he was heavily injured (0.68 tons of TNT) 

Count Olaf

Overall

• Nearly captured and killed the Baudelaires many times

• Escaped authorities many times

• Started many fires

• Played a role in the schism that broke apart the VFD

• Might have started the Baudelaire Mansion fire

• Defeated and killed Dr Montgomery, Aunt Josephine, Jacques Snicket, Olivia Caliban, Larry Your Waiter, and other VFD members

Power

• Slapped Klaus hard enough to send him to the ground and leave a bruise 

• Stopped door from being closed by stabbing it with a knife 

• Pushed Aunt Josephine overboard to her death 

• Sliced off head of a mannequin with a sword

• Lifted anchor over his head that Violet & Klaus needed to use rollers to move

• Threw slices of wedding cake hard enough to stun Violet 

• Threw a heavy book hard enough to break a window

• Was able to evenly arm wrestle Klaus & Violet at once 

• Stabbed a box full of Very Fancy Doilies and threw it into the air

• Beat Jacques Snicket to death with a crowbar offscreen

• Casually shattered multiple light bulbs with a crowbar swing

• Physically shoved around Hook Handed Man

• Destroyed submarine controls by hand

• Pushed a boat with the orphans inside to the edge of a pool

• Despite dying due to a harpoon in the chest, still had the energy to be able to carry a pregnant Kit

• Should scale to other displays of strength in his world

• Klaus can shatter vases and knock out grown men.

• Violet kicked a caravan door off its hinges.

• Violet & Klaus can both move large statues by shoving them.

• Sunny can bite through wooden pillars, the roots of trees, and the sides of an elevator shaft hard enough to emit sparks.

• The Bald Man carries around an anchor, which he used to hit the ground hard enough to make small shockwaves.

• The Hook Handed Man held a door against an angry mob and broke a hole in an ice covered lake with a single blow.

• Esmé carried/dragged an unconscious man up 66 flights of stairs, threw a shoe with a knife in it’s heel hard enough to embed in metal, and casually tipped over several large filing cabinets that Violet & Klaus struggled to lift.

• As a child, Lemony Snicket took on a man named Hangfire, who can smash through windows with ease, and later pushed him into the mouth of a monster.

• Aunt Josephine wrestled an alligator and threw a life sized metal statue of herself out a window.

• Jacques Snicket kicked down the door to a freezer.

• Jacquelyn Scieszka uprooted a tree as she was tied to it and knocked out the Hook Handed Man in a single hit with a tray.

• Kit Snicket broke a hole in the ice of a frozen river from below.

Speed

• Slipped away from the sight of Jacques Snicket

• Uhh he tends to run pretty fast ig

• Should scale to other speed feats done in his world

• Violet can shoot giant wasps out of the air

• Violet & Klaus were able to briefly chase after Olaf’s Car by running.

• Jacques dodged various objects tossed at him by Olaf.

• Esmé was able to fire a harpoon gun to accurately hit several books that were dropped from a hot air balloon, along with accidentally intercepting a crow.

• Carmelita managed to shoot down a crow mid flight with a slingshot.

• Violet is able to dodge sonic blasts 

Durability

• Got bitten by Sunny

• Survived a car crash, which in the series caused a large hedge to be moved

• Beaten up by angry mob

• Was made to suffer every hardship he forced the orphans through, including being on the wooden remains of a house that fell off a cliff, getting eaten by deadly leeches, and being trapped in his car as a train hit it

• Repeatedly shot at with various food stuff fired by gun made by Violet 

• Shocked by a faulty light switch

• Spun around before crashing into shed hard enough to knock it over

• Stabbed his hand while doing the knife game thing

• Survived boat wrecking in a storm

• Got shot in the gut with a harpoon and survived for about an hour before dying

• Should scale to other displays of durability in his world

• The orphans sailed a boat through a hurricane, got hit by blasts of steam, fell down an 66 story elevator shaft (though their fall was cushioned with a rope net), and rode a toboggan down a mountain on a sharp incline.

• They also survived a hot air balloon exploding into a small fireball, though the presentation of it makes it hard to say exactly how much they endured 

• Klaus endures being smashed by falling barrels of wine.

• Lemony Snicket as a child endured a beating from an adult named Stew Mitchum who had a cane and was in a train car as it crashed, and as an adult he was barely fazed by being tossed off of a trolley while in a box and tumbling for a bit.

• Dr Montogomery Montogomery survived being hit by a heavy lamp that fell on his head from a 2nd story window.

• Jacquelyn Scieszka was barely stunned by a fold up bed being dropped on her.

• Kit Snicket dove into a frozen river from high up.

Weaknesses

Sideshow Bob

As you may expect from a man who’s spent over 3 decades trying to kill a 10 year old boy, Bob is hardly flawless. His greatest weakness is his massive ego and love of the spotlight, wanting everyone to know he's brilliant. This is more often than not how his plans fall apart, due to him explaining his plots to whoever he has in his clutches, rather than just get on with it and kill them. Notably, when Bart & Lisa found out he had rigged the mayoral election, they managed to get him to confess to his entire plot in front of a packed courtroom simply by insinuating he had been a patsy instead of the mastermind of the plot. His ego also leads to him preferring not to make a simple plot, needing to kill Bart in a way that’s theatrical. Finally, his continued path of vengeance has also led to him spiraling into insanity, with his plots getting progressively more deranged, declaring a rivalry with an inanimate object, and seemingly suffering from vivid hallucinations. 

Count Olaf

While Count Olaf is a terrifying man, he’s far from a perfect genius. For one thing, his stamina can leave a lot to be desired, as he’s gotten winded from doing two jumping jacks and tends to be lazy and let his minions do more menial tasks. It's also hard to say how much of his success came from him being a genius rather than the rest of the world being oblivious enough to let him get away with it, which is something he himself has noted. This is best demonstrated in how his disguises are effective at tricking most normal people, but more intelligent people like the Baudelaires and VFD Agents can see through them since he usually only goes as far as covering up his unibrow, beard, or ankle tattoo. Finally, he’s also very determined to a fault, meaning he ended up getting tunnel vision on hunting down the Baudelaires at the expense of other goals such as keeping his allies on his side and alive, and this has led to his minions abandoning him and his sanity slipping, with his plots getting more deranged and violent as the series goes on. 

Before the Verdict

Wait, the Simpsons can scale to Futurama?

I for the most part didn’t include crossover scaling for The Simpsons, as things like the Family Guy crossover is firmly in non-canon territory, thanks to the presence of Kang & Kodos, whose appearances are usually a good sign that what you’re watching is not canon. That being said, I do feel Futurama is a bit more on the table in terms of potentially being fair game. Not only does the Simpsons have several instances of acknowledging Futurama for brief gags, but the full crossover episode has several elements hinting that it is well within the bounds of canon. Most notably, the episode ends with Bender going into sleep mode to get back to the future the slow way, and you can spot his sleeping form in the Simpsons house in several future episodes, which was confirmed to be intentional. However, most of the references to the Simpsons within the world of Futurama has The Simpsons be acknowledged as fictional in that world. And in their crossovers in the comics, it was explicitly established the Futurama cast getting trapped in an actual Simpsons comic in their world instead of actually going to the Simpsons world, and the context of the Simpsons later coming into the Futurama reality further reinforces that. Though the comic also has some weird meta shit as well that I am not getting into. This is all pretty weird to try and break down, but including this scaling or not ultimately doesn’t affect the verdict of this match much, so don’t worry too much about it.

Wait, if Olaf scales to Lemony Snicket, does that mean he’s comparable to the actual author of his books?

This is here mainly as clarification to anyone unfamiliar with the books wondering this, but to put it simply, no. The books are written with the framing device of Lemony being an in-universe character whose family was involved with the events, and is investigating and chronicling the events of the Baudilare’s lives after the fact. This is due to the fact he had fallen in love with their mother, only to let her leave him because she loved another man. He even has a prequel series starring him that discusses his past as a VFD agent. Additionally, as a bit of kayfabe for the kid fans, David Handler, the man who actually wrote the books, is in lore simply a guy Snicket uses as a representative due to being on the lam and not liking public appearances. To get back to the point, at no point in the original books or the movie does Lemony ever demonstrate anything implying he has some sort of omnipotence, reality warping, or other author abilities, and while the Netflix series does have him do some odd things, like pause time, walk around without being noticed, and take the audience into scenes of people acting out his analogies, this is likely just a visualization of his role as the narrator and not a literal ability the man himself has. So no, Olaf is not a metanarrative threat.

What about The Carmelita?

This is a fairly massive part of Olaf’s potential arsenal, and I feel like this would be incomplete without acknowledging it. Seen in The Grim Grotto, this is a massive octopus shaped submarine, powered by kidnapped orphans rowing, and possessing tentacles that are powerful enough to halt other submarines. While in the Netflix series, it was a rental, Olaf explicitly mentions stealing it in the books, and he boasted that he could use it to bring the armies of his enemies to their knees. That being said, it’s also not something he still has access to, as in both versions of the story that included it, Fiona and the Hook-Handed Man later end up hijacking it for themselves. Regardless, even if I did include it, the fact it’s a submarine means its usefulness in this kind of confrontation would be incredibly situational and incredibly unlikely to play a part in proceedings in anything besides super specific scenarios.

Verdict

(Track Art by @fmtthewomp)

Stats

Without involving scaling, the two are on a fairly similar level physically speaking, as both are reasonably above peak humans and survive plenty of slapstick. That being said, Bob definitely takes the advantage in durability, as he has a far more notable history of toughing it out though pain, and in far more varieties, whether that be blunt force, explosions, falling great heights, electrocution, being run over by various vehicles, and even having his face be ripped off. Olaf doesn’t really compare to this sheer variety of pain, and his own low stamina doesn’t help matters either, as Bob is typically able to go through all this pain with little that actually stops him.

When you start to bring up scaling, that’s really when Bob really takes the advantage. There are at least 5 pretty consistent feats that should all reasonably get up into the building level range, and there’s no reason not to scale Bob to these, as he does regularly pose a threat to Bart and the other Simpsons, who all reasonably scale to the other people doing these feats. Meanwhile, while they have admittedly not been calced yet, the best feats I could find for other characters in A Series of Unfortunate Events that Olaf reasonably scales to all appear to be well within the Street to Wall range at best, and while there are certain other entities within the verse I could see surpass that level, like The Bombinating Beast, the idea of Olaf directly scaling to them is very questionable. His submarine could also get up there, given it can overpower other submarines, but as mentioned, it’s not standard, and would be situational to bring in regardless.

Strength follows the same logic. In terms of talking pure lifting strength, Olaf actually could potentially get higher than Bob on his own even with the Brahma Bull strength, as Josephine tossing a metal statue could potentially be more impressive than Bob tossing a marble one, depending on the material and hollowness. However, Olaf also doesn’t have any strength feats that quite get up to the levels of the toonier feats of The Simpsons which Bob should also scale to, and his AP should scale to his durability, as he regularly harms people and gets harmed by people at that level. 

As for speed, the two really don’t have much on their own, though Bob does have a bullet reacting feat, meaning he should easily outpace any of Olaf’s scaling to harpoon firing feats. And bullet dodging is something that’s been done by Bart, Homer, and Krusty, all of whom Bob should compare to, which makes it fairly consistent. That being said, Olaf does manage to outpace simple bullet dodging thanks to his own scaling to Violet in the game, who is capable of blatantly dodging actual sonic blasts, which would take reacting at faster than sound speeds. That means Olaf actually takes speed, right?

For one thing, the games are fairly loose adaptations of the movie, which was already a very loose adaptation of the original books, so it’s hard to say how applicable it would be in terms of accuracy with scaling. It’s also only a single instance of this kind of speed, as well as being the fastest thing I could find in the series, whereas the bullet dodging is far more consistent from multiple sources across the Simpsons. And this feat for Olaf is really only in reaction speeds, as Bob is still significantly faster than him in terms of movement speeds, especially once their vehicles are involved.

Regardless, bullet dodging is also hardly the limit of Simpsons speed feats, as Abe Simpson was able to dodge a beam of light in his sleep, which is potentially far above anything Olaf’s done, as while beams of light do come up a bit in ASOUE, no one really can be argued to be able to react to and dodge them. You could also scale the Simpsons cast to the Futurama cast, as their crossover episode has been declared fully canonical, which potentially could get them into the MFTL range, though for this debate that’s likely just grievous overkill. The point here being, no matter how you slice it, I feel Bob is the one that will be faster more often than not.

Overall, regardless of if you use scaling or not, or how far into scaling you’d want to get, Bob is likely going to take stats here. If you don’t include it, Bob is a bit faster and stronger and far more durable, and the further you go into including scaling, the further the gap widens, as ASOUE is a far more grounded verse in terms of physicality than The Simpsons.

Arsenal & Abilities

When it comes to their respective arsenals, there’s a lot to discuss. Both have a wide swath of weaponry they use in close quarters, so they’d likely be about even in terms of melee combat options. The two’s disguise capabilities do kinda balance each other out. Olaf has a wider swath of options and personas to choose from, but Bob has the better track record in terms of people getting fooled by them, and his PMS Pinafore performance shows he’s able to pull them out of nowhere with no prep time. That being said, it’s ultimately unlikely to be a big deciding factor here. 

In terms of advantages, I’d say Bob’s arsenal would generally be overall deadlier. For starters, he has actual guns, which would definitely trump Olaf’s harpoon gun in speed and power. He’s also packing explosives, which would definitely get results far faster than Olaf’s slower fire starting methods. Finally, his options for ground transport trump Olaf’s car, as his bike would be significantly faster and more mobile, and his van is likely to come out on top in any attempted vehicular combat by virtue of being a big van charging an antique car. 

Though that’s not to say Olaf’s without his own advantages. He has several options for naval transport with his various boats, and his lions would definitely offer a potential avenue in terms of causing carnage, though Bob could likely overpower them. Most importantly, his various poisons would give him a pretty solid avenue to actually kill Bob regardless of the stat gap, as he’s not really demonstrated any sort of specific resistance to poisons. The injector, darts, anesthesia machine, and Medusoid Mycelium would all likely give Olaf the win should any of them manage to connect. Bob does have a poison of his own, but he’s only ever shown to deliver it with a basic syringe, meaning Olaf takes the edge in having more versatile methods for delivering it.

As for inherit abilities and skills, they surprisingly match each other pretty beat for beat, but Bob’s demonstrated far more impressive feats with what he has. Olaf does have training in stealth, but Bob’s demonstrated greater use of it, as he’s snuck around an actual military base. Olaf has some training in athletics to fall into trees, but Bob’s demonstrated far greater feats of acrobatics and flexibility. Olaf has utilized hypnotism in the past, but Bob’s methods towards it require far less set up in order to put into action, and are things he’s actually personally utilized. Olaf has fourth wall awareness, but while Bob himself hasn’t demonstrated it, the Simpsons tend to stay fairly loose with the fourth wall, meaning that’s unlikely to be an advantage. And Olaf has stage magic, but like, that’s just not going to be helpful.

And then there's the genetically modified elephant in the room. While some of Bob’s gene spliced abilities are admittedly not that useful, his Brahma Bull strength means he’s more likely to take the strength edge, his grasshopper thighs and wings mean he’s taking the acrobatics edge way easier, his enhanced eyesight and sonar would render Olaf’s attempts at stealth far harder, and his gills would mean he’d get a solid edge if Olaf attempts to take the fight to the water. The Zombie Ant Fungus rage could be a double edged sword, but in the episode Bob doesn’t really demonstrate any hits to his faculty when under the effects of it, so it’s likely not sending him into a mindless rage or something. And I’ll reiterate that I feel they are fair game, as there’s not been any confirmation on if and how he lost the abilities.

So ultimately, Bob does take this category overall. He boasts an arsenal that’s overall deadlier, and his skills and abilities surpass any displays Olaf may have with his. Though Olaf still has some options that Bob would have a hard time answering to.

Tertiary Factors

When it comes to comparing the two on an intellectual level, that’s actually something that’s a bit hard to lock down, as they have plenty of advantages over each other. Both are manipulative, classically talented, and have made many complex plans that let them dodge authorities. While Olaf does have the caveat of him mostly dealing with a world of idiots, Springfield is also hardly an intellectual melting pot itself. Bob is likely smarter on a purely intellectual level, given his wide knowledge on literature and science, but Olaf has better practical training which would come into play in a fight thanks to his time in the VFD. Olaf also takes the advantage in general mental stability, as while both can get pretty deranged, Bob’s the one where his insanity has gotten to be more of a potential active hindrance. Though on the other end, Bob is a lot more used to actually fighting and doing stuff on his own, whereas Olaf typically tends to let his minions do heavy lifting most of the time.

Now as for who could manipulate each other better, that’s a fairly hard question to lock down. Both are fairly good at manipulating others, whether that be idiot townsfolk or the smart children they face themselves with. On paper, Olaf might seem like the one to come out on top here, as he’s managed to find a higher success rate with what he’s accomplished with his plans, as well as being the only one of the two to boast an actual body count. That being said, context is important, and it’s important to note that the Baudelaires are typically able to immediately see through Olaf’s disguises, with his success coming more from them being helpless to stop him due to other circumstances until he’s close to succeeding. In contrast, while many of Bob’s plans also manage to go off without a hitch until endgame, the difference is that the Simpsons are typically not able to see through them and play right into Bob’s hands until he reveals and tries to murder them. And it’s typically a last minute ploy by Bart or his family that manages to get him out unscathed. So I’d overall say the net result here is that the two are very evenly matched on the intelligence end, meaning this would likely come down less to wits and more to their resources. 

Another thing to acknowledge is potential associate help, and there’s really not much question that Olaf is the one with the clear advantage here. He has at least double the amount of potential minions than what Bob could do with a family outing, with him having 10 between his troupe’s prominent members, Esme, the freaks, and Carmalita, whereas the only family members Bob would have to assist him amount to 5. He’d have an easier time coordinating them, thanks to his walkie talkies and spyglass. There’s also the fact that most of these minions are noted to be just as intelligent and competent as Olaf, if not more so. While Bob’s parents are implied to be very intelligent, there’s also the issue that Bob has actually utilized them in his plots far less than Olaf has with his minions. And in terms of what the ones with less screen time did, only his wife and son actually have helped him in a murder attempt, whereas his parents were more there to aid in his manipulation. The only one of them who has more than two major appearances to their name would be Cecil, who has a decent history of plots on his own thanks to the comics, but there is the issue that the two brothers have a rivalry, meaning he would be potentially less reliable as well. Bob’s family could potentially scale to stuff Bob scales to, but the only one who has anything really resembling feats suggesting scalability would be Cecil, meaning they'd still be outnumbered 2 to 10. 

Speaking of which, I feel it’s important to really break down the possibility of Bob dying to one of Olaf’s poisons. Now as mentioned, Bob hasn’t really demonstrated any sort of resistance to these, with the closest being that time he was in a storage locker as it was fumigated, but pesticide is pretty different from the poisons that Olaf is packing. As I said, Olaf’s methods would likely be effective in ending the fight, if they were given the chance. But to really break that possibility down, I believe that realistically Olaf’s poisons would be unlikely to edge him out a win. The venom injector would require Olaf to overpower or sneak up on Bob, which would be unlikely given Bob’s superior strength and stealth skills. The darts would likely affect him easily, but Bob scaling to dodging bullets means it’d be unlikely one of these would hit him in the first place. The anesthesia gas machine could knock Bob out, but it requires a mask be fitted onto Bob’s face for a couple seconds before taking effect, so unless he was somehow restrained it simply wouldn’t be effective. And the Medusoid Mycelium would be very devastating if it is unleashed, but it would also require an hour to take full effect, and during that time Bob would still have relatively full faculties until a couple minutes before he dies. 

Olaf could hypothetically trap Bob somewhere with the Mycelium with the help of his minions, at which point he’d run away to wait for it to take effect. Even if he does get infected himself in the process, he is likely aware of the cure to it, meaning it wouldn’t be a suicide move. However, Bob certainly has the stats and skills to eventually overpower Olaf’s minions and bust out of anything he could set up on short notice, his better land vehicles would mean he’s winning any potential car chases, and his skill in science thanks to his time at Monsanto Inc means the idea of him deducing the cure on his own is certainly plausible. In fact, in another odd bit of overlap, the horseradish/apple crossbred fruits that immunize you to the Mycelium’s effects are pretty similar to the GMO foods Bob was cooking up during the whole gene splicing business. Olaf does have his own methods of sea travel, but there’s realistically nothing stopping Bob from just stealing a boat from someone else himself and giving chase, and his gills would mean when he does catch up he’d be at an advantage at sea combat. Finally, if worse comes to worse, Bob killing Olaf only to die to the spores some time later would still technically classify as Bob taking the win, as Olaf would still be the first to die in this situation, and it’s not an explicit “suicide when you use this” ability. So while this is hypothetically a way Olaf can win, the odds are fairly stacked against that all going off without a hitch.

Finally, in case you were curious, if I included the non-canon material for Bob, then the match becomes far more uneven in his favor. In this material, Bob can revive himself from death, bring in corn based plant clones of himself, ride around in an animatronic mech suit, has a laser gun that can level buildings in a single blast, turn into a massive blob creature that absorbs people on touch, and split into two beings which can take on Stretch Dude and Clobber Girl, the former of which can dodge lasers and the latter of which can lift houses and the entire Statue of Liberty one handed. So, yeah, it’s a lot less close at that point.

Conclusion

“Listen to me! Life is short. Don't spend it on foolish, empty revenge!” 

Advantages:

• Far stronger, faster, and more durable

• Far greater stamina

• Overall deadlier arsenal

• Smarter intellectually

• Better at working solo

• Roughly equally good at manipulation

• Voiced by Kelsey Grammar

• Won an Emmy in real life and in universe

Disadvantages:

• Potential help is less in number and likely less reliable

• Has no known combat training

• Lower success rate 

• Has never (canonically) killed someone

• Rakes

• British

“Man hands on misery to man. It deepens like a coastal shelf. Get out as early as you can. And don't have any kids yourself”

Advantages:

• Better training 

• Potential help is more competent and greater in numbers 

• Poisons offer him methods which could kill Bob…

• Higher canonical success rate

• Actually has a canonical body count

• Roughly equally good at manipulation

• Played by both Jim Carrey and Neil Patrick Harris

• Doesn’t have hocus pocus or mind control, but still keeps his staff under his control

Disadvantages:

• Far weaker, slower, and less durable

• Worse stamina

• …though ultimately these methods would be difficult to pull off

• Arsenal otherwise is overall less lethal

• More used to working in a group

• Tried to marry a teenage girl like what the fuck man

Overall, this match has a lot to discuss, as the two are very tenacious in their goals and have many options for equipment and skills that make them a match for each other, especially intellectually. Count Olaf could certainly take the win against most if given the chance, given his poisons, better help, and better training. But when it comes to taking down Bob, his greater strength and survivability, overall deadlier arsenal, and more potent abilities and skills would mean Olaf would have little luck managing to win this Sideshow game. While Bob would have everything he’d need to deliver upon Olaf a Very Final Demise.

.

The winner is Sideshow Bob.