One of the most iconic recurring characters in The Simpsons is the failed television star turned attempted murderer Sideshow Bob. The nefarious (but comically inept) villain has been a consistent threat to Bart Simpson and the greater population of Springfield. The character works best when the show's creators perfectly meld his failures with a genuine sense of malice and terror. Along the way, his episodes have been among the best (and occasionally worst) entries in the series.
But how do they all stack up against one another? Here's every episode of Sideshow Bob, ranked.
THE MAN WHO GREW TOO MUCH
In the season 25 episode "The Man Who Grew Too Much," it's revealed that Bob has been made into the Chief Scientist for the genetic engineering company Monsarno. Having been a test subject for their experiments, he's risen in the ranks as a researcher. He actually finds a surprising friend and lab partner in Lisa, but their relationship falls apart when Bob reveals that his experiments have been altering his DNA to give him attributes and powers of other species. Terrified by his new state, he stops himself from killing the people around him by throwing himself into the river -- where he survives because of his modified body.
Far and away the worst episode featuring Sideshow Bob, "The Man Who Grew Too Much" takes an initially promising idea -- pairing Sideshow Bob and Lisa as intellectual peers -- and wastes it on an attempt to make the character a sci-fi horror fiend. While he works well in more horrific story beats, this episode pushes it to a point where even the most absurd Simpsons plot twists pale in comparison. Coupled with a forgettable subplot of Marge trying to teach abstinence to teenagers, the episode lacks any of the aspects that make for a memorable Sideshow Bob episode -- a grounded enough sense of humor and terror to make him believable.
FUNERAL FOR A FIEND
During a new attempt to kill the Simpsons, Bob ends up defeated and arrested. But during the trial, Bob and his family try to make the case that Bob has been driven insane due to his interactions with Bart. This slowly turns public opinion against Bart, who only makes things worse by becoming seemingly being responsible for the death of Bob while he’s on trial. But when Bart goes to try and make peace with Bob before he’s cremated, Lisa realizes it’s a trap and is barely able to lead the family to Bart in time to save him from Bob and his family.
While it’s nice to see Lisa take center stage as the one to defeat Bob fully for once in this season 19 episode (instead of just giving Bart an assist), the episode falls flat for more of the run-time than not. The entire Terwilliger family is on hand but don’t leave much of an impression, save for a cameo by Cecil where he talks to Bart about their mutual dislike for Bob and how it's shaped them to an extent. The entire family being in on the plan to murder Bart pushes the suspension of disbelief to a breaking point, leading to the entire family ending up in jail only to never appear again. While the episode swings for the fences, it fails to make any real impression.
DAY OF THE JACKANAPES
Bob is released from prison -- again -- and this time sets out on killing Bart and Krusty at the latter’s retirement celebration. To this end, Bob brainwashes Bart ala The Manchurian Candidate so that Bart can be used as Bob’s tool to murder the pair of them. But when Bob finds out that Krusty dedicated part of the final show to honor his relationship with Bob out of regret for the strain that came to define it, Bob has a change of heart and is able to warn Mr. Teeny in time to save the pair.
While there’s nothing particularly offensive or poorly produced in this Season 12 episode, “Day of the Jackanapes” suffers by comparison to the rest of the episodes featuring Bob. There are almost no elements (save a few jokes about Bart being hypnotized) that are wholly unique to the episode. Even ideas like Krusty retiring or throwing a massive anniversary show have been done better in other episodes. Predictable to a fault, the episode also turns Bob into a full-parody of himself, making him a completely comedic character instead of the threat he can be when he’s at his best. It's not necessarily bad, but there's nothing particularly original or memorable to it.
KRUSTY GETS BUSTED
The first Sideshow Bob episode is deceptive one. Airing towards the end of the first season, the episode centers around Krusty the Clown apparently robbing the Kwik-E-Mart, to Bart's dismay. Despite all the overwhelming evidence (including Homer being an eye-witness), Bart refuses to believe Krusty is guilty. Bob briefly takes over Krusty's show and intends to make it a more educational series, but Bart finds out he framed Krusty for the crime and he's taken to jail.
In this introduction to the character, Bob doesn't feel quite as fleshed out or specific as he would later become. Coming in the first season, "Krusty Gets Busted" is also a major introduction for Krusty as well. Informative and influential on the future of the characters, "Krusty Gets Busted" doesn't so much have flaws so much as it possesses the overall weaknesses of the first season of the series as a whole -- the animation is loopy, the writing is figuring itself out and the cast is still settling into their roles. But there's something inherently appealing about the characters, especially Bob, and shows how quickly it made sense to make the character.
THE ITALIAN BOB
This sixteenth season episode opens with the family traveling through Italy to deliver a sports car to Mr. Burns. Ending up stranded in a small Italian village, they discover that, after escaping custody at the conclusion of his previous appearance, Bob relocated overseas and made a home for himself in Italy -- including getting married and having a son. But when the Simpsons accidentally blow his cover, he swears revenge on the entire family and tries to murder them -- alongside his new family.
While the first act of the episode is all set-up for the Bob plot, the episode shifts gears well when it finds the core plotline. Bob’s attempts to be civilized are funny, and his eventual outing as a criminal is sudden but effective -- ruined by Lisa of all people. It becomes increasingly amusing when, unlike the town that turns on him, his wife and son go along with his plan to kill the Simpsons in revenge. It all builds to the Simpsons trying to evade them during a performance of Pagliacci starring Krusty -- because of course -- that includes Bob calming the horrified crowd with his operatic singing. It's a fun moment that leads to perhaps the character’s most sinister laughter ever, finding at least some level of balance between the humor and frightening aspects of the character. The worst part of the episode is that Bob’s family would be underutilized in future episodes. But that’s more of a flaw of future stories, not this one.
BROTHER FROM ANOTHER SERIES
After finding peace behind bars, Bob seems to have actually found redemption. Let into the custody of his brother Cecil as part of a work-release program, Bob soon finds himself hounded by Bart, who is convinced that he’s up to something nefarious. But the twist is that there is no reveal to Bob’s plans -- he genuinely is trying to go straight. Instead, it’s revealed to be Cecil who’s the criminal, intending to destroy the dam his company had been hired to construct so he can make off with a small fortune in stolen money while his brother -- and the rest of Springfield -- die to cover his escape.
At times, the Season 8 episode feels like the kind of stunt-casting that The Simpsons would later become beholden to -- casting David Hyde Pierce, who played Kelsey Grammer’s brother on Frasier, as Bob’s brother does nothing but draw attention to that other series. But once the episode finds a rhythm, it moves at a hilarious and harrowing pace. Bob’s attempts to go clean are punctuated with flashes of his telltale anger, but his brief partnership with Bart and Lisa to stop Cecil is full of great moments between the three of them. It helps that Cecil ends up being a surprisingly threatening character in his own right, even coming closer to killing Bart than Bob ever has by just picking him up and throwing him over the side of a dam. Although the episode ends with Bob back in prison and prepared for his next appearance (which skips over the character development he gains in this episode), it does begin the transition in Bob’s character that would eventually lead him and Bart to try and bury the hatchet in the future.
THE GREAT LOUSE DETECTIVE
When someone starts trying to kill Homer on the eve of Mardi Gras, the police release Bob into the family’s custody. While Bob tries to help Homer uncover the mystery behind who’s threatening him, Bob also continually hints at his own intentions to kill Bart as soon as he gets the opportunity. Although Homer is saved from the vengeful son of Frank Grimes, it's something he attempts in the final moments of the episode to no avail.
Season 14's “Great Louse Detective” isn’t so much flawed as it is scatter-brained. The episode features parodies of then-modern television, an entire opening act about a spa resort that only serves to introduce the plot and a twist that tries to connect the story to a far stronger episode, "Homer's Enemy." But "The Great Louse Detective" also gets a lot of mileage out of the Homer/Bob relationship, which finds an exasperated but genuine connection between the two. It also builds to one of the best moments of Bob and Bart’s relationship, reflecting how they’ve become more friendly rivals than mortal enemies by this point in the show: getting the open opportunity to kill Bart, Bob finds he can’t do it. He sings a song about their relationship and how he's even come to kind of respect him, despite himself. It’s a surprisingly complex shade to give Bob and Bart’s animosity that would be largely dropped in future installments but works well here.
SIDESHOW BOB'S LAST GLEAMING
During an air show at the Springfield Air Force Base, Bob escapes custody (again) and, in perhaps his most bold attempt at murder yet, steals a hydrogen bomb. He threatens to destroy Springfield if they fail to completely shut off all television in the town. Bart and Lisa, trapped on the base with him, end up discovering his plan and help foil it -- but not before Bob kidnaps Bart so they can perform a kamikaze attack on the one man who ignored Bob’s demands: Krusty.
Consistently hilarious, Season 7's “Sideshow Bob’s Last Gleaming” finds a hard balancing act between making Bob the butt of the joke or making him actually threatening. While some moments don’t land as well as they could (particularly in his motivations, an argument against television that he never really makes outside of his intentions to turn the Krusty Show more educational in “Krusty Got Busted”), the episode ends with a frantic and enraged Bob stealing the Wright Brothers Plane to try and kill himself and two others. Those moments, especially the way he bellows what he believes will be his death cry, show Bob at some of his most fearsome and frantic. The fact that it’s completely pointless (with the plane bouncing off Krusty’s shack before being crushed by a tank) is the perfect comedic touch on the moment, giving Bob a level of comic ineptitude that doesn't detract from his scarier aspects.
The most recent Sideshow Bob episode (at least until next year’s "Bobby, It's Cold Outside"), and what could have easily been the last appearance of the character. When Bart falls into an abandoned bunker in the woods without any way to contact help, Springfield spreads out to try and find him. But when the search is called off, Bob escapes from his prison appointed psychiatrist to find him -- and kill him -- himself. But things take a turn when Bob actually finds Bart with the forced help of Milhouse.
What follows is a surprisingly thoughtful Sideshow Bob episode from Season 29, as the criminal mastermind is forced to confront the reality of his situation. His perpetually patient psychiatrist is a recurring element in the episode, forcing Bob to have flashes of sanity punctuated by stylized bouts of madness. The episode also has a lot of fun pairing Bob off with Milhouse of all people, forcing the young boy to take him to Bart by singing light operetta. While the episode isn’t perfect, it does include a genuine moment of reconciliation and understanding between Bart and Bob. Bart outright asks Bob if it’s worth everything he’s done just to murder a young boy, leaving Bob actually speechless. The two even hug at the end, content with the revelation that Bob didn’t stab him -- and Bart didn’t put a Kick Me sign on his back. It all leads to a brief epilogue sequence that shows Bob later in life, regretting his earlier commitment to vengeance that consumed his life. It gives Bob a complete arc, something almost no one on The Simpsons has ever fully received.
THE BOB NEXT DOOR
When Springfield is forced to release a majority of non-violent offenders back into the public because of a lack of resources, one of them moves in next door to the Simpsons. While most of the neighborhood is immediately won over by Walt Warren, Bart remains terrified because of his voice -- which sounds exactly like Sideshow Bob. He continues to think so even when he sees Bob in maximum security but tries to come to terms with his anxiety to go out to a baseball game with him. But that's when Whitman reveals he is Bob -- having knocked out the real Walt Warren and, using surgical tools in the prison, cut off Warren's face to replace with his own.
It's maybe the darkest appearance of the character ever, taking Bob into a complete horror movie direction. Even other appearances from Sideshow Bob at their scariest aren't as outright frightening as the sequence where Bob cuts off his own face and sews on another while fully conscious. His ultimate plan to kill Bart falls apart in large part thanks to Bart's suspicious nature never allowing him to trust Warren This allows for Warren's Jimmy Stewart character and his innocent nature to play off perfectly against Bob and the rest of the crimes he commits. Plus, while it may be one of the more outlandish Sideshow Bob episodes, the horror is still grounded enough in the usual comedy of the Simpsons world to keep it consistent.
SIDESHOW BOB ROBERTS
With Springfield facing a mayoral election in the coming weeks, a swell of conservative arguments leads Mayor Quimby to release Sideshow Bob from prison. He quickly throws his hat into the election and actually wins, becoming the most powerful person in Springfield. He immediately makes life difficult for the Simpsons, forcing Bart and Lisa to try and prove that Bob won the election fraudulently -- otherwise, they risk losing their house to his plans.
One of the best political satires the series has ever attempted, “Sideshow Bob Roberts” is a highlight of the sixth season of the show. However, Bob is less of the villain of the episode than the concept of the Republican Party as a whole. This episode largely uses Bob as a tool rather than a character, with his hatred for Bart being largely muted as a result of his intentions. But in the process, he becomes a villain for the entire town, at least for an episode This episode is more focused on mocking pretty much every aspect of politics in quick succession, while still featuring some solid characters beats from Bart and Homer. While it’s not the best Bob episode, it is one of the better episodes period and deserves recognition for that if nothing else.
The second appearance of Sideshow Bob occurs in the third season and features Bob at perhaps his most realistically devious. After meeting Selma through a prison pen-pal program, Bob seemingly commits himself to reformation. Eventually released, he proposes to Selma and the pair are promptly married. But a suspicious Bart eventually uncovers a plot by Bob to kill Selma to steal a small private fortune she’s ended up with.
While there are some fun bits after Bob’s full plan is revealed (particularly his inability to keep himself from promising to kill Selma during a foot rub), the episode is largely one of the darkest Sideshow Bob episodes. Bob is actually treated with a sense of malice, coming remarkably close to fulfilling his mission and murdering Selma on-screen. Bob himself is never treated as a comic figure. Only the second episode largely featuring the character, and the writers discover the perfect balance for him: funny things may happen to him and his response to them can be silly, but for the character to work there needs to be a genuine threat. While other episodes would lose that balance at times, "Black Widower" finds a happy medium.
In this fifth season episode, after being released from prison, Bob makes his mission very clear: he’s going to kill Bart and be done with it. To get away from all of his threats, the Simpsons are moved into witness protection. But Bob follows them to their new home of Cape Feare and is able to corner Bart alone in the middle of the night on a drifting house-boat. It comes down to Bart having to try and outthink Bob if he wants any chance of escaping him.
A high mark of the entire series and maybe the single funniest episode of the show, “Cape Fear” finds the tricky balance of having Bob be both hilarious (his tattoo that says "Die Bart Die"is just German for "The Bart The") and terrifying all in good measure. There’s something unsettling about how casual he is in his threats against Bart, and no matter how many rakes, cactus or elephants get in his way, he’s still able to sneak into a ten-year old’s bedroom in the middle of the night with a machete. Even the absurd ending, where Bart plays into Bob’s showmanship and gets him to sing the entirety of the Gilbert and Sullivan opera H.M.S. Pinafore to stall for time, concludes with Bob drawing a blade and preparing to gut the boy. It’s the perfect example of how Bob should work, and he's an undeniably funny character that's the closest thing the show has to life-or-death stakes.