Most 10-year-old boys do not have an enemy, let alone an arch enemy whose sole purpose is to kill them. Bart Simpson (Nancy Cartwright), though, is not your typical 10-year-old, and Sideshow Bob (Kelsey Grammer) is not your typical villain. It's a classic rivalry, up there with Wile E. Coyote vs. Road Runner, Batman vs. Joker, Itchy vs. Scratchy... and so on. This dynamic has provided some of the best episodes in The Simpsons’ 30+ seasons. Read on, and you just might learn about nutrition, self-esteem, etiquette, and all the lively arts.
15. “The Italian Bob” - Season 17, Episode 8
This episode finds the Simpsons in Italy, picking up a Lamborgotti Fasterossa for Mr. Burns. They end up in the idyllic Italian town Salsiccia where it's discovered that Sideshow Bob is mayor. His townspeople don't know of Bob's past, and he has settled down with a wife and son, Francesca (Maria Grazia Cucinotta) and Gino (Tress MacNeille). He begs the Simpsons to keep his secrets, which they agree to do. Naturally, however, the Simpsons mess up Bob’s tranquil life, prompting him and his family to seek revenge.
The worst of the lot. There's no outrageous schemes, and no intention of killing Bart at first sight. Bob is domesticated, for lack of a better word, and the idea he is now a family man seems wrong. This episode lacks almost everything that makes Sideshow Bob episodes special, and leaves our antagonist simply boring.
14. “The Man Who Grew Too Much” - Season 25, Episode 13
Lisa, after researching the benefits of GMOs, finds out the chief scientist behind GMOs from Monsanto is none other than Sideshow Bob. Sharing a common bond with the works of Walt Whitman, Bob and Lisa spend some time together, eventually visiting the local museum. Saving Lisa from a falling exhibit, Bob reveals he has been changing his DNA with those of intelligent people and the various strengths of animals. Now in a murderous rage, Bob takes Bart and Lisa to Springfield Dam, where he threatens to kill them. Stalling Bob by asking him to sing, the sibs are rescued, and Bob attempts suicide by drowning, only to escape thanks to the presence of gills.
This episode has a "been there, done that" vibe that's hard to shake, like asking Bob to sing in order to stall him, and another change of heart. The revelations of Bob's new abilities are fun, but, considering most Sideshow Bob episodes have at least some rooted reality, seems out of place.
13. “Gone Boy” - Season 29, Episode 9
Bart enters the forest and disappears into an abandoned military installment. After searching for hours, he is assumed dead. Milhouse (Pamela Hayden) knows the truth, but doesn't tell, enjoying the opportunity to console Lisa. Sideshow Bob, distraught that he didn't kill Bart, discovers the truth and forces Milhouse to bring him to Bart. He ties them up to a Titan II missile and is going to launch and kill them, but has a change of heart at the last moment. By this point, we've seen Bob not follow through with his murderous plans because of a change of heart one too many times, lessening the impact of his appearance, and the episode as a whole.
12. “Brother From Another Series” - Season 8, Episode 16
Sideshow Bob leaves prison on a work release program, and into the custody of his brother Cecil (David Hyde Pierce), who is the engineer behind a new hydroelectric dam being constructed. It's soon discovered that Cecil has been embezzling money from the hollow and poorly constructed dam, and had plans on scapegoating Bob. Working together, Bart, Lisa, and Bob prevent the destruction of the dam. Cecil is arrested, as is Bob. Reuniting Grammar and Pierce (who played brothers on Frasier) should have been great, but instead Pierce shows up as the sole antagonist of the episode, leaving Bob the hero to save Bart, Lisa and the whole town. Sideshow Bob is at his best when he is solo and psychotic. A decent episode nonetheless.
11. “Funeral for a Fiend” - Season 19, Episode 8
Sideshow Bob sets up an elaborate scheme to kill the Simpsons by luring the family to a fake BBQ restaurant. He is stopped, but a secondary scheme even more elaborate than the first leads to the death of Bob (Spoiler: not really) and another attempt at ridding the world of Bart. Another average entry, with nothing that really makes it stand out from the others. Fun fact: This marks the second, and so far final, time we see Bob's family.
10. “Sideshow Bob’s Last Gleaming” - Season 7, Episode 9
Sideshow Bob sets his sights on the mindless drivel state of television programming, vowing to rid the world of it. Escaping from work duty at an Air Force base, Bob finds a 10-megaton nuclear weapon, and threatens to blow up Springfield with it unless they stop all television broadcasting. All but Krusty comply, which is enough to make Bob detonate the device. But he should have checked that best before date of November 1959. The device is a dud. It's a pretty average entry, certainly not Bob at his best, but has its moments.
9. "The Bob Next Door” - Season 21, Episode 22
The Simpsons get a new neighbor, Walt Warren, who sounds identical to Sideshow Bob. Bart is convinced that it actually is Sideshow Bob, but he looks nothing like Bob and, besides, Sideshow Bob is still in prison. Convinced that Walt isn't Bob after all, Bart goes with Walt to the Isotopes' game. Only, it isn't Walt - it is indeed Sideshow Bob, who, in a great call out to Face/Off, has switched faces with the real Walt, and is now free to kill Bart at Five Corners, where five states all meet. "The Bob Next Door" is a welcome throwback to the earlier Sideshow Bob episodes, where Bob simply wants to kill Bart and devises a crazy plan to do so.
8. “Bobby, It’s Cold Outside” - Season 31, Episode 10
Sideshow Bob is found living as a lighthouse keeper, but is offered a job as a mall Santa at Springfield Mall. At the same time, someone is stealing Christmas gifts from porches throughout Springfield. Denying himself an opportunity at killing Bart, describing it as being out of character for Santa, Bob offers to help find the true thieves. The thieves, C. Montgomery Burns (Harry Shearer) and Waylon Smithers (also Harry Shearer), are soon caught, with Burns confessing his depressing experiences with Christmas. Sideshow Bob, as Santa, helps Burns see the good in his experiences, resulting in all the presents being returned. With shades of The Grinch throughout, it's not the most original episode, but does contain a hilariously exaggerated PC take on "Baby, It's Cold Outside."
7. “The Great Louse Detective” - Season 14, Episode 6
Somebody is trying to kill Homer, so Chief Wiggum (Hank Azaria) suggests that they need someone who can understand the mind of a murderer to help figure out whom. That someone is Sideshow Bob. He is freed from prison, but with a shock device attached to his leg to keep him from attacking Bart. You know what they say - helping hands aren't harming hands.
6. “Treehouse of Horror XXVI” - Season 27, Episode 5
In the “Wanted: Dead, Then Alive” segment of the annual horror fest, Bob succeeds in killing Bart. His greatest desire finally fulfilled, Bob becomes a literature teacher, but quickly learns that the only passion he truly had was hunting Bart. He builds a reanimation machine which revives Bart, allowing Sideshow Bob to kill him again, setting off a kill/reanimate cycle where Bob kills Bart in a variety of ways. The Treehouse episodes are among the series' best, and seeing Bob finally succeed... and succeed... and succeed is weirdly rewarding.
5. “Day of the Jackanapes” - Season 12, Episode 13
Bob, enraged that Krusty publicly admitted to taping over all archived episodes of Bob on The Krusty the Klown Show with episodes of Judge Judy, hypnotizes Bart and sends him off to kill Krusty. This time, Sideshow Bob himself stops the proceedings after hearing Krusty's sincere regret for Bob's mistreatment at his hands. Sure... but would he have been so quick if it were The People's Court?
4. “Sideshow Bob Roberts” - Season 6, Episode 5
Sideshow Bob is put forward as the Republican candidate for the Springfield mayoral election, winning the seat by an overwhelming majority, a number of which are false votes for Bob from the dead (including a vote from Lisa’s (Yeardley Smith) beloved pet Snowball), Bob is found guilty of electoral fraud, stripped of his title, and returned to prison. An episode that manages to throw in some good political humor along with the usual Bob vs. Bart hijinks.
3. “Krusty Gets Busted” - Season 1, Episode 12
Krusty the Klown (Dan Castellaneta), a robber? The ever-vigilant Kwik-E-Mart security cam footage would certainly indicate so. But a large shoe size, and Bart's determined insistence that Krusty is innocent, thwart Sideshow Bob’s plans to incriminate Krusty and take over the show for himself. This episode set the template for Bart vs. Bob episodes to follow.
2. “Black Widower” - Season 3, Episode 21
Sideshow Bob marries Selma (Julie Kavner), a seemingly loving union, until the whole blowing up the room on the honeymoon while Selma is still inside, post-MacGyver business. A brilliant scheme, but thwarted by Bart at the last minute. This episode highlights Grammer's strengths as a voice actor, giving Bob a full range between hopeless romantic and murderous psychopath.
1. "Cape Feare" - Season 5, Episode 2
The best of the lot, hands down. In this brilliant parody of Cape Fear, Sideshow Bob is on the loose, forcing the Simpsons into the Witness Protection Program. There are so many memorable moments: Homer (Dan Castellaneta) and his inability to grasp that he is now Mr. Thompson; Bob attaching himself under the Simpson's Thompson's car, his vote to not drive through the cactus patch the losing minority; a pitch-perfect piece of comic timing involving Bob and an unfortunate number of rakes to step on; and the one-man HMS Pinafore show. Perfection.