Sideshow Bob is one of the most iconic Simpsons side characters. It’s easy to see why. Even among the eras fan consider the chaff of the series, Bob is usually a highlight. The character has been there since Season 1 and has made sporadic enough appearances that he hasn’t worn out his welcome.
Sideshow Bob has been in a lot of episodes, but not all of them are substantial. In doing research, there are literally episodes where all Bob does is cringe. So this list will focus on his major appearances from worst to best. We're ranking from lowest to highest starting with #16.
16. "Funeral for a Friend"
Sideshow Bob’s plan is WAY too convoluted and not in a fun way. Bob blows a perfect opportunity for revenge (especially since his previous appearance established he has enmity with the whole family). I like some things about this episode. I like the idea of bringing in Bob’s entire family, but Cecil (who appears in maybe two scenes) is the only one with a backstory, so the writers had to invent backstory. How Lisa figured out Bob’s ruse was clever, and I like the idea that Sideshow Bob convinces everyone he’s the good guy. But these ideas are in the service of a pretty lousy episode.
15. "Wedding for Disaster"
This episode is pretty bad. And Sideshow Bob only has a small part where he’s a red herring in a kidnapping scheme. But Sideshow Bob’s cameo—where he actually gets along with Krusty—is one of the only good parts. Bart’s specious reasoning is one of the few genuine laughs. This episode was somehow worse than the previous, but Sideshow Bob almost salvaging a lousy episode deserves a little credit.
14. "The Man Who Grew Too Much"
One of the drawbacks of social commentary is that when it rubs the viewer the wrong way, it really becomes annoying. This episode tries to make big statements about GMOs and a lot of it feels like the dollar store "Lisa the Vegetarian." Though it is interesting to see a new side of Bob as his obsession with GMOs turns him into a superhuman. Plus, we see him interact with Lisa without feeling like some belabored attempt to answer why he has no grudge against her. There’s also a B-plot about Marge teaching an abstinence course. Like most of the social commentary of this ilk, it’s a lampoon of how narrowminded and one-dimensional this mindset is. Of course, the commentary is narrowminded and one-dimensional. I mean, this is a worthy target, but still.
This episode was salvaged by one thing: It was the late Marcia Wallace’s last episode and there’s a touching tribute to her at the end. Yeah, this mediocre episode gave me feelings. Though I’d recommend watching that part and skipping the rest.
13. "Treehouse of Horror XXVI"
Hard to believe it took this long for Sideshow Bob to appear in a "Treehouse of Horror." Many of his episodes feel like horror spoofs, so that should have been a no-brainer. But his big appearance is a doozy. Sideshow Bob kills Bart. I knew of this episode’s reputation for Bob repeatedly killing Bart, but it turns out that was the payoff rather than the premise. And it works. The image of Bob keeping Bart’s corpse around the house is pretty creepy. And surprisingly, this episode does have a happy ending. It’s a good thing this segment is buoyed by the gruesome imagery because the humor is hit and miss. Speaking of hit and miss, the Godzilla spoof is so-so even if the attempt at meta-fiction was at least interesting. The Chronicle spoof was decent, considering I’ve missed that movie.
12. "The Italian Bob"
Parts of this episode are pretty good, parts are pretty bad. On one hand, it introduced Bob’s family who became pretty entertaining characters. The scene where Bob decides where he wants to start over is the comedic highlight. And this is a pretty sprawling episode. The plot about the Simpsons going to Italy to pick up a car for Mr. Burns is used later, making it feel like someone wrote an outline. And I cannot say that about every episode from this era. The ugly Americans narrative really gave an excuse to make Homer act obnoxious. And while it was an accident, even Lisa feels obnoxious in outing Bob’s criminal past. I just felt sorry for Bob in a way I did not like. Still, this episode has more good than bad. So, if you’re a Sideshow Bob fan, check this one out.
Also, there’s a joke where Homer mistakes Mussolini for Donald Trump. Some jokes are just layups…
Read More From Reelrundown
11. "Day of the Jackanapes"
It’s amazing that there was a time when The Simpsons could do jokes about shows getting stale without feeling like a cop-out. This episode does suffer from all-too-familiar story beats. The scene where Bob is paroled feels like the writers were desperately trying not to repeat a similar scene from "Cape Feare." But this episode overall works. Jokes about studio notes feel evergreen. Sideshow Bob’s role feels quite similar as he plans to kill Bart and Krusty pretty gruesomely and actually has the upper hand on Bart for the lion’s share of the episode.
10. "Bobby, It's Cold Outside"
This is another episode where Bob plays the hero, even if the story feels a little zig-zaggy. It’s also not that hard to figure out who the actual culprit behind the mystery is. Though a predictable outcome is preferable to a nonsensical cheap gag - which was to be expected from this era. And the motivation actually makes sense instead of just being a cheap gag. My only gripe with this episode is that the ending drags a little with an extra ending that feels tacked on. Also, there’s a Scott Bakula cameo for the win. The end of this episode is surprisingly wholesome. It’s funny how despite his numerous wrongdoings, Sideshow Bob is likable enough that him getting a happy ending actually feels good.
9. "Krusty Gets Busted"
Being the first Sideshow Bob episode, we see different sides to the character before crime became his dominant feature. The idea of him trying to convert Krusty’s show into a much more high-brow show is unique. Plus, we actually saw Bob in a prior episode… just one… and he had a different design. But that is more continuity than many shows of this vintage would have bothered with. Plus, the episode does a decent job setting up Bob’s motive, and how Bart figures out Bob committed the crime was clever.
8. "Gone Boy"
Surprisingly, the Christmas setting has little to do with the plot. But the snowy setting does give the episode plenty of atmosphere. One reason recent Sideshow Bob episodes have been decent is that they test new relationships – like Bob with Milhouse. Bart spends much of the episode in a bunker and it leads to some pretty funny gags. The final act ups the ante with laughs and stakes. And it ends on a weirdly heartwarming note, made even weirder by Bob committing a pretty serious crime (albeit by accident).
7. "The Great Louse Detective"
We see a lot of different sides to Sideshow Bob: Bob as a hero and a rare pairing of Bob and Homer. The Simpsons delight in torturing Bob, which is understandable. Plus, we get a clever tie-in to another episode (which is too good to spoil). This episode has several big laughs, making me wish I could rank it higher. But it loses points over some moments of Homer the jerk and a few other jokes that clang. But the bad jokes are over quickly enough.
6. "The Bob Next Door"
This is another example of The Simpsons just going for joke after joke and actually working. One problem with modern Simpsons is the number of jokes that feel like they needed the brakes pumped. We see one or two of those, but there are way more hits than misses in this episode. Bob’s plan is convoluted, but this time it’s in a fun way. Even jokes like the cop who talks like Andrew Dice Clay are so dumb they circle back to being funny. Some viewers may be turned off by scenes of faces falling off. But those who can stomach it will be rewarded with one truly funny episode.
5. "Sideshow Bob Roberts"
I forget where I saw this, but someone once pointed out that maybe The Simpsons didn’t consistently predict the future. We’ve just always had the same problems. Despite some jabs at the Republican Party, one would have to be a gloomy Gus to take issue with this episode (incidentally proving Kelsey Grammer has a sense of humor about his politics). Especially since they get some jabs at the Left. It’s also interesting to see Bob grind his ax with the Simpsons in a different way – no attempted murders, just making their lives miserable. I also like that the writers remembered Bob was a children’s entertainer, which he uses to his advantage. My one nitpick with the episode is that while Birch Barlow is a brilliant spoof of Rush Limbaugh, we do feel the characters’ frustration with his tedious talk.
Though one burning question: Why is Dr. Demento Bart’s other mortal enemy?
4. "Brother from Another Series"
Bringing in Sideshow Bob’s brother could have been a cheap gimmick. Bringing in the actor who played Kelsey Grammer’s brother on his most famous show could have been gimmicky. But they made it work. Cecil is an entertaining character without being a clone of Bob or Niles Crane. He and Bob have good chemistry – those two played brothers for a reason on Frasier. This was the first time Bob plays the hero and his desperation to prove he’s not the bad guy offers some laughs. Bob’s line about shampoo is an underrated gem. And Homer’s line about doing your own dirty work wrecks me every time.
3. "Black Widower"
After a bizarre non-speaking part in "Bart the Murderer" (where he buffed up), Sideshow Bob made his first full comeback. This episode has some choice gags – Bart trying to explain gas exploding to Homer, an odd scene of Barney driving the hansom cab. But The Simpsons doesn’t get enough credit for its cinematography and coloring, both look great in this episode. Sideshow Bob’s scheme has holes… actually, they’re more like questions. Like was he really willing to (a-hem) blow his whole scheme because he didn’t like MacGyver? Maybe it was part of his scheme. Maybe that was a bridge too far for Bob. But the episode is so good those problems don’t matter. Though I could live without the somewhat petty dig at Jim Henson’s Dinosaurs.
2. "Sideshow Bob's Last Gleaming"
The joke-writing was on point – the slow chase, Grandpa mistaking the port-o-potty for an elevator, a great Dr. Strangelove spoof, and Krusty’s ham-fisted attempt to be the only TV show running. The guy who eats people and steals their faces is such a quick throwaway line that wrecks me every time. But after some of Bob’s serious but more personal crimes, it’s interesting to see the stakes raised this high with Bob threatening Springfield with a nuclear weapon. I also like that the writers of this episode remembered that this whole mess started with Bob’s feud with Krusty.
1. "Cape Feare"
I didn’t have to think too long about my favorite Sideshow Bob episode. In fact, this may be my favorite Simpsons episode full stop. There have been Simpsons episodes that go for social commentary. Some go for heart. This one just goes balls-to-the-walls for laughs. Nearly every joke is a home run – Mr. Thompson, Homer’s brownies, and the rakes. Oh God, the rakes. Kelsey Grammer’s “Lurch cringe” is one of the great sound effects. And they weren’t afraid to go full wacky – like Airplane or The Naked Gun – with stuff like Bob singing the HMS Pinafore.
The episode is a less than subtle spoof of Martin Scorsese’s Cape Fear remake. You don’t need to see the movie to get the jokes – as I’m sure most of us didn’t when we were seven. Though if you are familiar, seeing their takes on famous scenes makes some of these gags even better. It’s funny how this parody feels like it has actually overshadowed the film. But despite being nonstop jokes, this episode did inherit some atmosphere from the film.
More Ranking Articles
- Ranking Every Mel Brooks Film
Mel Brooks is a comedy legend with dozens of films under his belt. But how does each film compare to the others?
- Ranking the Ernest Movies
Hey Vern! It's time to rank every Ernest movie from worst to best
- Ranking Every Episode of It's Always Sunny in Philadelphia Season 13
The Sunny Gang just wrapped their 13th season. How did each episode fair?
Favorite Episode on this List?
© 2022 Alex deCourville