In movies and TV, every hero needs a villain. In The Simpsons, young Bart (Nancy Cartwright) might be the bad guy himself sometimes, but he’s a good kid at heart. Many times during The Simpsons, he’s had to go toe to giant clown shoe with the evil Sideshow Bob (Kelsey Grammer), the former sidekick of Krusty the Clown who now wishes death to Homer and Marge’s oldest child, and who many times has tried to make that happen. It has always been funny to watch Sideshow Bob get defeated, but he’s also one of the creepier cartoon characters you’ll ever find due to just how ruthless he is and Grammer’s impeccable voice performance. Still, there have been times when Sideshow Bob hasn’t been so bad. In two Christmas episodes of The Simpsons, he and Bart have even been almost like friends, turning one of TV’s most memorable bad guys into a toothless, well, sideshow of himself.

Sideshow Bob Has a Change of Heart in “Gone Boy”

Sideshow Bob could never kill Bart Simpson. This is The Simpsons, after all, not Game of Thrones. It’s rare for animated shows to kill off characters (sorry, Maude Flanders), and Bart will certainly never die. Heck, he can’t even age. Still, Sideshow Bob is a complete lunatic in early episodes like “Cape Feare,” where he certainly tries his best. Sideshow Bob is not a softy, but in two Christmas episodes, he becomes just that. The holiday season is supposed to be all about good times and coming together, so The Simpsons chose, unwisely, to lean into that and make friends out of foes.

The first time this happens is in the Season 29 episode “Gone Boy,” a play on the popular Gone Girl novel and movie. First airing on December 10, 2017, we find an imprisoned Sideshow Bob outside collecting trash by a highway with his fellow inmates. On the same highway, Homer and Bart are out for a drive, as the family is on a Christmas vacation. With Bart needing to pee, he walks out into the woods for some privacy, only for him to fall through a manhole cover under the leaves into a military bunker with a nuclear missile inside. Meanwhile, a search party, including the inmates, goes looking for Bart. Sideshow Bob wants to find and kill him, but when the search is called off and the boy is assumed dead, Bob is upset that he wasn’t the one responsible for it.

Later, a prison therapist tells Bob that Bart’s death can free him, but Bob won’t believe he’s dead until he sees the body himself. He escapes from prison and forces Milhouse, who has known where Bart was the whole time, to take him to his friend. Sideshow Bob then ties the two pals to the missile, but as the launch countdown commences, he remembers what his therapist says and decides that he wants to do good. Bob unties the two boys and hugs them, telling Bart he doesn’t want to kill him anymore. While it’s good that he had a change of heart, it came out of nowhere simply because of a chat with a doctor. Rather than being earned, it’s a quick feel-good moment for a Christmas episode.

Sideshow Bob Takes His Role as Santa Claus Seriously in “Bobby, It’s Cold Outside”

Sideshow Bob was front and center again for another Christmas episode of The Simpsons on December 15, 2019, for “Bobby, It’s Cold Outside”. Bob is out of prison and living in a lighthouse where, to celebrate the season, he’s making tree ornaments of dead Barts. One hangs from a noose, another has a knife to the heart, and another an ax to the head. You get the picture. When a woman, another lighthouse keeper, comes over and asks if he has any secrets, Bob flashes back to his hatred for Bart. He’s then offered a job as an amusement park Santa, taking it only because it’s the lead role.

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You know what’s gonna happen next. Bart goes to visit the Santa only to find out that it’s the villain of his life underneath the white beard. Bob ties Bart up with Christmas lights, ready to kill him, but he can’t do it because he’s a method actor who can’t step out of character. He’s committed to playing Santa Claus and can’t quit just to simply murder his archnemesis. After hours, Bart goes back to the park, where he encounters Bob, who swears he’s not going to kill the boy. To get Bob to prove it, Bart enlists him to help find out who has been stealing the packages of Springfield residents. He finds the culprit, Mr. Burns, and gets him to confess that he’s the thief and give everyone’s presents back for a happy Christmas morning. It’s another feel-good moment for the holidays, but an even bigger head-scratcher than the previous episode. Sideshow Bob has made it his life’s mission to kill Bart, but he gives it all up to play an amusement park Santa? More confusing, as the episode ends, Christmas is over but his urge to destroy Bart doesn’t return.

The Simpsons Run Into Sideshow Bob on Their Vacation in ‘The Yellow Lotus’

Sideshow Bob’s latest appearance on The Simpsons was in this season’s episode “The Yellow Lotus”. It’s the opposite of Christmastime in this one, with the Simpsons going to a fancy island resort in the summer called the Yellow Lotus (a spoof of the TV series The White Lotus). It’s there that the family runs into Sideshow Bob staying in the room next door with a woman who is his new wife. Bart wants to know what his evil plan is this time, but Bob swears he’s not up to anything. For whatever reason, they decide not to tell the woman about Sideshow Bob’s criminal past as long as he stays out of trouble. Unable to keep it in any longer, Marge tells the woman about Bob’s villainous side, but she doesn’t believe her. However, the twist is that it’s Bob’s new wife who tries and fails to kill him when she pushes him off a cliff.

An episode of The Simpsons with Sideshow Bob used to mean mayhem, with Krusty’s former sidekick absolutely obsessed with Bart to the point of madness. He may have never reached his goal, but he still stayed a madman and was always back to try again. Sadly, it seems like The Simpsons has gotten bored with this approach in the past few seasons. They’re over Bob as being an attempted killer and don’t know what to do with him, so now he’s either backing out of his nefarious plans for the silliest of reasons or, like in “The Yellow Lotus,” he doesn’t even have those plans at all anymore. Sideshow Bob is now just another character, and Bart’s life is safe from harm. Where’s the fun in that?

The Simpsons is available to watch in the U.S. on Disney+.

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The Simpsons

Release Date

December 17, 1989

Seasons

36

Studio