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Top 10 Best Sideshow Bob Episodes

VO: Rebecca Brayton WRITTEN BY: Thomas O'Connor
A worthy nemesis is hard to find. Welcome to, and today we’re counting the Top 10 Best Sideshow Bob Episodes. For this list, we’re looking at the finest Simpsons episodes in which Bart locks horns with his arch-enemy, the sophisticated and poofy-haired Sideshow Bob.

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A worthy nemesis is hard to find. Welcome to, and today we’re counting the Top 10 Best Sideshow Bob Episodes.

For this list, we’re looking at the finest Simpsons episodes in which Bart locks horns with his arch-enemy, the sophisticated and poofy-haired Sideshow Bob.

#10: “The Italian Bob” (2005)

When Mr. Burns sends Homer to pick up his new car directly from the factory, the Simpsons get a free trip to Italy. However, a cheese-related mishap leaves the family stranded in a small Tuscan village. When the family goes to meet the mayor, they’re shocked to find that it’s none other than Bart’s old enemy, who’s settled down with a family and put his life of crime behind him. Unfortunately for Bob, the unexpected guests put his secret past back in the spotlight. It’s a sharp deviation from other Bob episodes, and, though it may be less memorable, its originality earned it a place on our list.

#9: “The Bob Next Door” (2010)

Having a crazed maniac come after you multiple times would leave any 10-year old with lasting trauma and paranoia – we’re surprised Bart isn’t seeing flashes of Bob just about everywhere. But when a new neighbor joins the Simpsons on Evergreen Terrace, Bart becomes convinced that it’s actually his old foe in disguise, and it might not just be his repressed trauma talking. This episode calls back to a few classic Simpsons gags, with yet another throwback to the famous rake bit – and even a scene that takes place at “The Five Corners”, which was last seen way back in season 6! Delivering plenty of nostalgia mixed with fresh jokes, it was an episode worthy of this beloved villain.

#8: “The Great Louse Detective” (2002)

Despite his affable nature, Homer’s made a few enemies over the years, and one of them apparently isn’t messing around. In this episode, a mysterious assassin makes several attempts on Homer’s life. Given the Springfield Police Department’s less-than-stellar success rate at solving crimes, Homer goes to the most experienced criminal he knows to try and figure out who’s behind the string of assassination attempts. With a shock collar-equipped Bob to lend some insight into the criminal mind, the family eventually learn the killer’s identity. Seeing Bob and Homer work together wasn’t just a novel concept, but a hilarious odd couple pairing for the ages.

#7: “Day of the Jackanapes” (2001)

With declining ratings, Krusty the Klown decides to finally bid showbiz adieu, announcing his retirement for a fifth time. When Krusty reveals he’s taped over every episode featuring his former sidekick Sideshow Bob, Bob flies into a rage and plots revenge. Again. In a rare show of effectiveness, Bob then captures Bart as part of his plan to kill both him and Krusty. Obviously, things don’t go to plan, and Bob is probably still kicking himself for not finishing Bart when he had the chance. Inevitable conclusion aside, it’s an episode with solid laughs and a wonderfully convoluted plot; one that put both Bob’s genius and his tendency to overthink things front and center.

#6: “Sideshow Bob’s Last Gleaming” (1995)

In this classic episode, Bob turns his rage toward television after growing tired of what he sees as a cavalcade of dull banality polluting the airwaves. Remember, this was 1995, and “Breaking Bad” and “The Wire” were a long ways off. In a convoluted scheme to rid Springfield of television, Bob breaks out of prison and steals an atomic bomb, interrupting the family’s day out at the local air show. While far from the best of Bob’s schemes, this caper still features some great moments, like Bob’s impression of an army Colonel voiced by none other than R. Lee Ermey of “Full Metal Jacket” fame.

#5: “Brother From Another Series” (1997)

This episode brought many new elements to the table, giving more of a sense of depth and intrigue to Springfield’s resident evil genius. When Bob is released from prison, again, he’s reunited with his estranged brother Cecil, who gives Bob a job working at a construction site building Springfield’s new hydroelectric dam. This episode introduced David Hyde Pierce as Sideshow Cecil, and the fact that the actor also played the brother of Kelsey Grammer's character on “Frasier” isn’t something the episode was shy about mining for comedy. Cecil would appear later on in the series as well, but this first appearance is still his best.

#4: “Sideshow Bob Roberts” (1994)

What’s worse than a megalomaniac villain who’s clearly gone off the deep end? One who’s entered politics. After repeatedly calling in to a right-wing radio show, Bob becomes the darling of Springfield’s chapter of the Republican Party. With the help of his new Republican allies, Bob runs for Mayor of Springfield and wins. Naturally, having his arch-nemesis as the mayor makes Bart’s life a whole lot harder, but he and Lisa quickly discover Bob’s mayoral win is a bit suspicious. This is another classic Sideshow Bob episode, with Bob’s villainous schemes providing material for plenty of jokes directed at Republicans and political conspiracies alike.

#3: “Krusty Gets Busted” (1990)

Every story has to start somewhere, and the rivalry between Bart Simpson and Sideshow Bob began with this episode from the show’s very first season. When Bart’s idol Krusty the Klown is arrested after seemingly having robbed the Kwik-E-Mart, Krusty’s sidekick Bob speaks for the very first time and takes over as host of his TV show. But Bart and Lisa have their doubts about Krusty’s guilt, and their investigation into the robbery begins a rivalry that would last for decades. This marks the very first appearance of Kelsey Grammer as Bob, and the start of Bob’s career as an arch-villain and criminal mastermind. To call this episode a classic is an understatement.

#2: “Black Widower” (1992)

We all want to find love, but sometimes that search can lead you down some dangerous paths. When Aunt Selma brings her new boyfriend to meet the family, Bart and Lisa are shocked to see that the object of her affections is none other than Sideshow Bob. Rather than accept that Bob has repented for his crimes and has nothing but the best intentions, the duo put him under intense scrutiny – something that eventually saves Selma from certain death. Not only did it set the tone for future Bob episodes, but gave us a fully fleshed-out Sideshow Bob; a villain worthy of multiple guest appearances spanning decades.

#1: “Cape Feare” (1993)

It wasn’t the first time Bob and Bart crossed paths, but it’s undoubtedly the best. Heavily modelled after the 1962 film “Cape Fear” and its 1991 remake by Martin Scorsese, the episode sees Bob paroled from prison… only to quickly make clear his intention to put Bart six feet under. Fearing for their lives, the Simpson family go into witness protection. A landmark episode that firmly cemented the Bob/Bart dynamic as well as Bob’s love of Gilbert and Sullivan (not to mention a deep hatred of rakes), this is the Bob episode to rival them all, and one of the best episodes in the entire series.


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