Every Sideshow Bob Episode Of ‘The Simpsons,’ Ranked

On Sunday’s episode of The Simpsons, we were treated to a cameo appearance from Sideshow Bob, who is an inmate at the prison where Bart’s ultra-strict substitute teacher (voiced by Willem Dafoe) becomes a guard. So now is a great time to rank every Sideshow Bob episode ever. Just to be clear, we’re only counting episodes that centered around Bob, so Sunday’s episode and “Wedding For Disaster,” where he also had a cameo appearance, will not be inlcuded.

Now then, on to the fun!

12. “The Man Who Grew Too Much” – Original Air Date: March 9, 2014

When I started putting this together, I couldn’t remember what happens in this one. Considering that it’s not even a year old, that can’t be a good sign. In case you forgot too, this is the one where Sideshow Bob gets super strong from experimental drugs after he becomes the Chief Science Officer at the prison. Why they would put a clearly insane person in charge of that is beyond me. I mean, yeah, he’s smart, but you have to draw the line somewhere. I could deal with leaps of faith like that if the laughs were there to back it up, but this one didn’t have a lot going for it.

11. “Funeral For A Fiend” – Original Air Date: November 25, 2007

The question of what would happen if Sideshow Bob died is an intriguing one, but sadly the answer was “a really boring episode.” First off, the notion that the entire town would turn on Bart and support a man who repeatedly attempted to murder a child is completely ridiculous. Secondly, Sideshow Bob’s big feet being utilized as the solution to the story was already done in the first Sideshow Bob episode, so that just felt lazy. The only good thing about this one was John Mahoney guest starring as Sideshow Bob’s dad, making the Frasier connection complete.

10. “The Great Louse Detective – Original Air Date: December 14, 2002

This episode relies far too much on shock humor. I mean that literally — about half of the episode is just Sideshow Bob getting shocked over and over again. Apparently, the writers found that a lot funnier than most of the viewers did. Still, this one isn’t devoid of redeeming qualities; the idea of Sideshow Bob teaming up with Homer to solve the mystery of Homer’s killer is interesting, as is the ultimate reveal of Frank Grimes, Jr. looking to avenge his father. Still, this episode seems like a waste of potential, especially the tacked-on ending with Sideshow Bob having a chance to kill Bart, but deciding he can’t because he’s “grown accustomed” to Bart’s face. When Sideshow Bob’s singing ruined his scheme in “Cape Feare,” it was clever. This time it just seemed lazy.

9. “Day Of The Jackanapes” – Original Air Date: February 18, 2001

I still don’t understand this one. In Sideshow Bob’s previous appearance, he was reformed and no longer homicidal. Now, he wants to kill Bart AND Krusty? Okay, maybe being falsely imprisoned at the end of “Brother From Another Series” made him crazy again, but this is NEVER mentioned. Instead, he’s angered that Krusty taped over his old episodes, while Krusty is sick of network notes, so he decides to retire. This culminates with Sideshow Bob trying to kill both of them in a dynamite explosion at Krusty’s final show. The whole storyline was underwhelming, and Sideshow Bob’s motive should have been explored more. Still, I can’t hate an episode that has Homer’s line about “gettin’ drunk at the old flower shop.” I use that one in conversation a fair amount.

8. “The Italian Bob” – Original Air Date: December 11, 2005

Sideshow Bob escapes to Italy and is free of the Simpsons once and for all … or so he thinks. Naturally, when the family greets him in the Italian village, they screw everything up, with the lone difference being that this time, a drunk Lisa is the culprit. This one is fairly enjoyable, combining a travel episode with a Sideshow Bob episode. The Simpsons escape Sideshow Bob’s wrath yet again, while his urge to kill them all grows stronger than ever. Most of all, I’ll remember this one for reminding us that cheese insurance does not cover mortadella.

7. “The Bob Next Door” – Original Air Date: May 16, 2010

Let’s not beat around the bush here: yes, the face-switching thing is weird. Like, really weird. Probably the grossest thing The Simpsons has ever done outside of the “Treehouse Of Horror” episodes. I can certainly understand why that turned some fans off, but I’ll argue that the rest of this episode is entertaining and clever enough to make up for it. Bart being frightened by a new neighbor who sounds exactly like his arch-nemesis is a great concept, as is Bob’s plan to kill Bart at the Five Corners — he fires a bullet in one state that kills Bart in another, therefore no crime has been committed. The face thing is weird, but there’s still a lot to like about this one.

6. “Sideshow Bob’s Last Gleaming” – Original Air Date: November 26, 1995

My least favorite of the Golden Era Sideshow Bob episodes, but it’s still a pretty strong episode. I was particularly entertained by Sideshow Bob correctly guessing that “Rock You Like A Hurricane” would play at the air show, and R. Lee Ermey playing an intense drill sergeant who happens to enjoy making Garfield references (“My wife told me that was gangbusters.”). This one isn’t as perfect from start-to-finish as “Cape Feare” or “Sideshow Bob Roberts,” but it is a really funny 23 minutes of television, and it gave us that immortal line about haulin’ ass to Lollapalooza.

5. “Krusty Gets Busted” – Original Air Date: April 29, 1990

The first appearance of Sideshow Bob! The Simpsons weren’t fully developed in the first season, and at times this one lacks the quick pacing that would drive the best seasons. With that said, this is an extremely well-done episode. We can appreciate how sick Sideshow Bob is, not just of Krusty’s frequent abuse, but of the lowbrow comedy he’s being forced to perform when he has such loftier ideas in mind. After framing Krusty for armed robbery, he turns Krusty’s old show into a smart kids show, which Lisa appreciates (“He’s a lot less patronizing than Krusty used to be!”). Eventually, his big feet betray him, and Bart becomes his lifelong enemy. A great introduction for a fantastic character.

4. “Black Widower” – Original Air Date: April 9, 1992

Poor Selma. Despite her best efforts, she just can’t seem to find the right guy. At this point in time, the format of Sideshow Bob episodes wasn’t so well-established, and it seemed possible that he might really be a changed man. But of course, that’s not the case at all. I like that the MacGuyver storyline ended up tying into Sideshow Bob’s murderous plot, as he attempted to kill her while she watched the show by herself. This was the episode that firmly established Sideshow Bob as an all-time lunatic, and set the stage for the brilliance that was “Cape Feare.”

3. “Brother From Another Series” – Original Air Date: February 16, 1997

I mean, come on, if you were casting Sideshow Bob’s brother, the obvious choice would have to be David Hyde Pierce. He put on a brilliant performance as Cecil in what more or less acts as an honorary Frasier episode. In an amusing twist, Sideshow Bob really has changed this time, and Cecil is the murderous one. This is irrelevant to Chief Wiggum, however, as he decides to just throw both of them in jail. This ending is a bit awkward, but the witty dialogue between Bob and Cecil is still enough to make this an all-time classic episode.

2. “Sideshow Bob Roberts” – Original Air Date: October 9, 1994

As fine a piece of political satire as The Simpsons has ever done, with Limbaugh stand-in Birch Barlow being a particular source of laughs, complaining about the “spendocrats” and their “bleeding heart smell-fare program.” Sideshow Bob runs for mayor and has no problem getting elected despite being an attempted murderer. Of course, Mayor Quimby’s incompetent mayoral campaign doesn’t help either (“If you were running for mayor, he’d vote for you.”). There was also the amusing tragedy of Lisa seeing that Snowball II voted for Sideshow Bob. Of course, Bob gets caught, but now he’s a white collar criminal and prison is a much more pleasant experience (“We need an eighth to row against the Princeton alums!”). Anyway, this one is just about perfect from start to finish.

1. “Cape Feare” – Original Air Date: October 7, 1993

Did you expect it to be anything else? Sorry for being predictable, but this episode is absolutely flawless, and is one of the best episodes in Simpsons history. Everything from the legendary rake scene to “HEY BART YOU WANNA SEE MY NEW CHAIN SAW AND HOCKEY MASK?” to “h, maybe you all are homosexuals too!” to “Hello, Mr. Thompson,” to the fantastic H.M.S. Pimafore scene is just brilliant. I could watch this episode every day and never get tired. There are several great Sideshow Bob episodes, but this one easily tops the list.