Lifetime of Simpsons

Murder and Rakes: Sideshow Bob Episodes Ranked



Hi there everyone, and welcome to my second week of wrap-up here on Lifetime of Simpsons. This whole week is going to be built on one of the internet’s favorite activities. Ranking things! So, over the next five days I’ll be ranking different frequent types of episodes. And we’ll be starting things off by discussing one of my favorite categories of Simpsons episodes. Sideshow Bob episodes! Ever since the very first season we’ve been getting occasional stories that take a pretty radical departure from the feeling of the rest of the show. Because, fourteen times over the past 29 years we’ve gotten to experience weird little mystery episodes, primarily focused around Bart Simpson trying to deal with attempted murderer and former children-entertainer, Robert Underdunk Terwilliger, Jr, better known as Sideshow Bob. And I love these episodes so much. The idea that Bart Simpson has a murderous nemesis who has repeatedly broken out of prison in order to kill him and destroy Springfield. All because Bart helped prove that he framed Krusty the Klown for robbing a convenience store. Bob is a great character, brought to life by Kelsey Grammer’s consistently great performances, and his episodes are almost all incredibly solid. But, some are certainly better than others. So let’s talk about that.



14. “The Bob Next Door”


Bob Next Door

I’m of the opinion that there hasn’t been a truly bad Sideshow Bob episode. They’re all pretty fun, and make for weird little departures to the normal order of episodes. But, there was certainly a strange trend in the Sideshow Bob episodes over the past decade or so. They’ve gotten incredibly weird. They used to be pretty grounded episodes that just dipped into the world of crime. But, slowly, they started to become utterly absurd. And “The Bob Next Door” is probably my least favorite of the whole bunch because of this. This was the episode where Sideshow Bob performed surgery on himself in order to switch faces with another convict in order to escape prison and kill Bart. And it’s just a little too weird to hold together for me. Seeing Sideshow Bob pull a New 52 Joker and just rip his own face off was just a tad over the line for me, pushing the episode too far into absurdity. There’s still some good gags, and it’s a very silly and weird episode, it just doesn’t hold up that well when compared to its siblings.


“The Bob Next Door” was written by John Frink and directed by Nancy Kruse, 2010.




13. “The Man Who Grew Too Much”


Grew Too Muh

Now, while the idea of Sideshow Bob cutting his own face off in order to pull of an evil scheme was just too much for me, the idea of him genetically splicing himself into a literal supervillain was just a bit better for me. “The Man Who Grew Too Much” is a super strange episode, from top to bottom. It doesn’t reveal itself to being a Sideshow Bob episode until about halfway through, it’s about Lisa being tricked into thinking that Bob is rehabilitated and befriending him, and it ends with Bob literally gaining superpowers in order to take over the world only to be bested by a group of mindlessly horny teenagers. Objectively, this is a dumber episode than “The Bob Next Door.” And yet, it’s so stupid that I find it just a tad more enjoyable than “The Bob Next Door.” This is a very stupid episode, but it’s so dumb I find myself enjoying it. At least more than “The Bob Next Door.” Which isn’t exactly a ringing endorsement, but hey, this is my dumb list and I can rank these however I want.


“The Man Who Grew Too Much” was written by Jeff Westbrook and directed by Matthew Schofield, 2014.




12. “Funeral for a Fiend” 


Funeral Fiend.jpg


But, no matter how fun those two episodes are, the fact that they’re so strange, and go so far outside the structure of a Sideshow Bob episode makes it hard for me to really like them. Which is how an episode like “Funeral for a Fiend,” which is an incredibly dull Sideshow Bob episode, manages to beat them. “Funeral for a Fiend” really feels like they were working off a Sideshow Bob checklist, just going through the motions. And yet, there is one thing that this episode has going for it. I’ve always found the idea that Sideshow Bob is just a murderous Frasier pretty funny, and this episode doubles down on the far superior “Brother From Another Series” by tossing in the late John Mahoney as the pair’s father, Dr. Robert. It isn’t a perfect episode, and not even a really great episode, but it’s the insistence to sticking with the gimmick is enough to inch this one above the previous two episodes.


“Funeral for a Fiend” was written by Michael Price and directed by Rob Oliver, 2007.




11. “Wanted: Dead, then Alive”


Dead then Alive


I cannot believe that it took twenty six years for the show to put Sideshow Bob in a Treehouse of Horror episode. And boy was it exactly what you’d expect it to be. Seeing Sideshow Bob recreate an Itchy and Scratchy episode by brutally killing Bart again and again while using some sort of device that brings him back to life is fun. It’s very dumb, but it’s pretty fun. Obviously, since this is just a segment of a Treehouse episode it doesn’t have a whole lot to it, and it doesn’t really get into any of the things that I enjoy about Sideshow Bob stories, the mystery, but there’s still a certain cathartic joy to be found in this episode, letting Bob vent his frustrations. But, that’s about it.


“Treehouse of Horror XXVI” was written by Joel H Cohen and directed by Steven Dean Moore, 2015.




10. “The Italian Bob” 


Italian Bob.jpg


And speaking of that catharsis, “the Italian Bob” is an episode that really shows off why Sideshow Bob hates the Simpsons. This episode, which initially masquerades as a vacation episode, only for the Simpsons to randomly encounter Sideshow Bob in Italy, trying to start a new life. And, of course, the Simpsons ruin all of that, even though it’s by accident. The Sideshow Bob half of this episode is pretty fun, but the fact that the first act meanders with the vacation aspect, which ends up leaving this episode in kind of a weird state. It’s not a great Sideshow Bob episode, and it’s not a great vacation episode. There’s aspects of it that work really well, and I like Bob in the episode, but it’s just not one of the best examples of what a Bob episode can be.


“The Italian Bob” was written by John Frink and directed by Mark Kirkland, 2005.




9. “The Great Louse Detective”


Great Louse


It does seem like the show started to worry at a certain point that they needed to do something new with Sideshow Bob. Even though the episodes that followed the formula were all great, they apparently figured they needed to change, and try new things. Which resulted in episodes like this. “The Great Louse Detective” wasn’t a very traditional Sideshow Bob episode, but I do enjoy the idea that they flipped the script and had had Bob investigating a murder rather than planning one. The way things pan out, what with the secret son of Frank Grimes coming to kill Homer in revenge for the death of his father, is pretty weak, and the worst part of the episode. But, having Bob be forced to pal around with the Simpsons, and especially Homer, was a pretty fun idea, even though it never really had any hope of besting one of the classic episodes.


“The Great Louse Detective” was written by Jon Frink and Don Payne and directed by Steven Dean Moore, 2002.




8. “Gone Boy”




It was a very pleasant surprise to find that the latest Sideshow Bob episode, and one of the latest episodes in general, was a pretty fun one. Yeah, it still doesn’t follow the classic Sideshow Bob formula that I know and love, but it’s still quite a bit of fun. It takes a while for Bob to really become important in the episode, but when he finally escapes from prison in order to find Bart and finally get his vengeance, things really kick into gear. But, the things I find most interesting about the episode is the ending. Like I said in my article, it really feels like this is meant to be the final Sideshow Bob episode. It ends on a note where Bob finally realizes that this fixation on the destruction of Bart Simpson is a hollow pursuit, and that he should finally just give it all up and lead a normal life, and that’s fascinating. He realizes that he’s just going through the motions, concocting an evil plan not really because it means anything to him, but because that’s just what he does. And, when confronted with that realization, he decides to finally change. Who knows if that will actually stick, but it’s an interesting way to end the saga of Sideshow Bob if they choose it to be.


“Gone Boy” was written by John Frink and directed by Rob Oliver, 2017.




7. “Day of the Jackanapes”




“Day of the Jackanapes” is one of the last episodes of the more classic Sideshow Bob episodes, and the first to really buck the formula and try something different. And I think it succeeded more than any of the previously mentioned episodes. There wasn’t a mystery to solve, but getting to see Sideshow Bob plan an elaborate assassination attempt on Krusty the Clown while killing two birds with one stone and also killing Bart is pretty fun. The lack of a mystery is a serious downside to this episode, but it gets a huge step-up by the fact that it’s a very fun and funny episode. It’s full of great bits, and we get to see plenty of Bob being pure evil, which is pretty damn fun. Even if it’s not exactly the deepest episode.


“Day of the Jackanapes” was written by Al Jean and directed by Michael Marcantel, 2001.




6. “Black Widower”




Now we’re getting cooking. The last bunch of episodes on this list are all going to classic ones, stories that fall into what I consider to be the true formula for a Sideshow Bob episode. This was the second episode that really featured Bob, and it really cements what most of the episodes in the future would be modeled after. This is a story where Bob gets out of prison and plans an elaborate scheme to get rich by marrying and then killing Selma, and he would have gotten away with it if it wasn’t for that meddling Bart. I really love the mystery of this episode, especially when it straight up becomes an Agatha Christie story with Bart telling us all what happened. The only problem with this episode is that it can be a tad forgettable. I think that’s mostly due to the fact that it revolves so heavily around Selma instead of Bart. But, it’s still a really fun little mystery.


“Black Widower” was written by Jon Vitti, Sam Simon, and Thomas Chastain, and was directed by David Silverman.




5. “Krusty Gets Busted”


The.Simpsons_S01_E12_Krusty.Gets.Busted 082


And then there’s the episode that started it all. The first season of the Simpsons is such a strange assortment of stories. The show was trying to figure out what it wanted to be, and it certainly seemed to believe that being a Bart-centric show was the right route to take. So, they put Bart in a bunch of different scenarios, one of which was to put him in a mystery story. It’s funny to think back on the long tenure of Sideshow Bob and remember that it all began with him framing Krusty for armed robbery, just because he wanted control of the show. It’s such a relatively minor thing to have thrown him down a path that would eventually lead to him almost firing a nuclear bomb at Springfield just a couple months ago. This episode lays the foundation of what a Sideshow Bob episode should be, and introduces the central conceit that I’ve always found so strange and enjoyable. Bart Simpson has never been portrayed as the brightest bulb in the bunch, and yet he has a preternatural skill at solving Bob’s schemes. He’s able to notice things that no one else can, even the police, and time after time brings Bob’s schemes tumbling down. And it all begins with this episode, which succeeds in making it all believable and fun.


“Krusty Gets Busted” was written by Jay Kogen & Wallace Wolodarsky and directed by Brad Bird, 1990.




4. “Brother From Another Series” 




This is an episode that’s probably best remembered for its gimmick. Because it’s a great gimmick. The idea to have Sideshow Bob have a heretofore never-mentioned brother who is voiced by fellow Frasier castmate David Hyde-Pierce is a hilarious one, and it ends up working beautifully in this episode. It’s full of funny Frasier references which make for classic and memorable gags, but it’s all bolstered by a really great mystery. The idea that Bart just can’t believe that Bob has gone straight is a lot of fun, and seeing him and Lisa stalking Bob, waiting for him to slip up leads to a lot of great moments throughout the episode. Plus, the revelation that Bob actually was on the level this time, and that Cecil is actually the one behind the evil scheme this time, assuming that everyone would just blame Bob is fantastic. We have an episode that captures everything that I love about Sideshow Bob episodes while also bucking tradition and trying something new, which apparently was a nigh impossible task. But they nailed it.


“Brother from Another Series,” was written by Ken Keeler and directed by Pete Michels, 1997.




3. “Sideshow Bob’s Last Gleaming”




It’s interesting that “Gone Boy” featured Bob attempting to use a nuclear bomb on Springfield, since he’s tried that and failed once before. But, I don’t think that there’s really any debate that his first attempt lead to a much better episode. “Sideshow Bob’s Last Gleaming” is an absolutely hilarious episode, and while it doesn’t feature a whole lot of mystery, it more than make up for that with terrific gags. We do get to see Bart and Lisa on the case, working hard to stop Bob’s schemes, which I love, and it’s made even better by how absolutely insane this episode is. I mean, Sideshow Bob attempts to kamikaze Krusty the Clown in the Wright Brother’s plane by the end of this episode. Things really go off the rails. But it is a hell of a ride.


“Sideshow Bob’s Last Gleaming,” was written by Spike Feresten and directed by Dominic Polcino, 1995.




2. “Sideshow Bob Roberts”




This episode is basically everything that I want from a Sideshow Bob episode. We get Bob getting out of prison for a ridiculous reason, him planning an incredibly elaborate crime, Bart and Lisa slowly unraveling the whole thing, and then a climactic and dramatic revelation of misdeeds before Bob can be arrested again. All while wrapped up in a hefty dose of political satire, making for one of my absolute favorite episodes of all time, let alone Sideshow Bob episodes. This story is just so wonderful, and I love the added twist of having Bob attempt to destroy Springfield, and Bart, through a less murderous route. Having him run, and get elected, for mayor of Springfield all as an evil plot is a whole lot of fun, regardless of current political similarities. Bob’s reign of terror is brief, but it’s kind of refreshing to see him win for once. And man do I love the fact that in the end he’s brought down by his own hubris, refusing to admit that he isn’t a tactical genius. It’s just great stuff, folks.


“Sideshow Bob Roberts” was written by Bill Oakley and Josh Weinstein and directed by Mark Kirkland, 1994.




1. “Cape Feare”




“Cape Feare” is a hell of an episode of television. When I went back and looked at all of the articles I wrote about these episodes, I was a little surprised that my reaction to this episode upon revisiting it was a little off. At the time I complained that the episode wasn’t really fitting into my strict definition of what a Sideshow Bob episode should be. And, while I still do maintain that I’m a sucker for an episode with Bart trying to solve some sort of mystery, it becomes clear when looking at this list that that actually didn’t happen very often. So, even though “Cape Feare” doesn’t really feature that strong of a mystery, I still have to admit that it’s my favorite of the bunch. It’s just such a solid episode. Having the Simpsons hide, unsuccessfully, it witness protection is a really fun idea, and then having Bob so easily see through that and continue his single-minded revenge against Bart is great. But, where this episode really shines is that ending. While Bob may be a homicidal genius, Bart Simpson knows how to push his button, and Bob’s vanity is always an assured way to get him off his game, which is done to terrific effect in this episode. I just love it so much.


“Cape Feare” was written by Jon Vitti and directed by Rich Moore, 1993.



So there you have it. Fourteen stories about a grown man trying to brutally kill a ten-year old boy who has continuously been a thorn in his side. It still delights me that the people behind the Simpsons decided that a recurring feature of this show should be to include episodes where the members of the Simpsons family have to deal with a murderous kids-show host, let alone the fact that they’re some of the strongest episodes of the series. Sideshow Bob is just a terrific character, and the fact that the show has been able to craft more or less consistently enjoyable mystery stories featuring him for the past twenty nine years has been a treat to experience again over the course of this project. I don’t know if we’ll see Bob again during the tenure of this show, but he’s always a welcome addition to the show.




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