Best Sideshow Bob Episodes of the Simpsons

The Top Ten

1 Cape Feare - S5

In the sequel of The Simpsons Movie Sideshow Bob needs to be the villain.

Actually, the episode with Sideshow Bob in season 21 was really good and maybe a little bit disturbing. (That's the one where Sideshow Bob exchanges faces with his cellmate)

THE RAKES! *slam* yehhohohohoh *slam* yehhohohohoh etc...
- Oreanta

Who wants to drive through this cactus field? That is such a funny scene (and so is the part where he passes out from writing with his blood).

2 The Bob Next Door - S21

The Bob Next Door was the best voted episode in that season but had a few minor bits in. The way Bob's feet cracked when the waitress took off Bob's and Walt's face transplants and the way Bob used Anesthetic on Walt at least punch him...

This was bob's most successful plan to get rid of Bart. if Walt hadn't escaped, bob could have succeeded.

This episode was amazing, but at the end instead of telling bart his plan, he could have already killed him.

Very shocking and actually we'll put together.

3 Brother From Another Series - S8

I really liked this one because it actually put bob as a good guy and that was a neat twist.

Bob's brother Cecil plots to flood springfield - CrowdedChisel

Greater Frasier parody! I love it.

An amazingly funny episode

4 Sideshow Bob's Last Gleaming - S7

Utterly, excellent great things happen. If you want to see it go to HMV and buy Season 7.

Bob attempts to cut off TV from Springfield - CrowdedChisel

Awesome! Better than other S.B. episodes

5 Sideshow Bob Roberts - S6

Great episode but cheating is not always the answer to win the election...

6 The Italian Bob - S17

I like how Sideshow Bob's wife still loves him after she found out that he trying to get his revenge on Bart, unlike other wives. Also the son is very cute when he kept on shouting "Butterfly Revenge." Sideshow Bob's wife is also very pretty.

The Simpsons go to Italy only to find Bob is the mayor of a small town - CrowdedChisel

Sideshow Bob is featured on the cover of the Season 17 DVD.

Hey mambo. Mambo Italiano... (Burps like Barney)

7 Krusty Gets Busted - S1

Bob frames Krusty for armed robbery - CrowdedChisel

8 The Great Louse Detective - S14

I love this episode but there is one problem: It is the what started The Simpsons being digitally animated (the season 7 episode "Radioactive Man" was digitally animated but it went back afterwards and it is this episode where it becomes permanently like it) - 445956

Homer is being followed by a mysterious murderer who Bob is assigned to capture - CrowdedChisel

9 Funeral For a Fiend - S19

This episode is really clever, but not particularly funny. The opening five minutes could also just have been thrown away, as they add nothing to the story and are pointless setup. - MrKite

Bob fakes his own death so it looks like Bart killed him - CrowdedChisel

That my favourite episode of bob.

The coffin is too obvious.

10 Black Widower - S3

Bob is released from prison and marries Selma to try and get her money - CrowdedChisel

Luckily Selma didn't marry Bob.

A overall great episode

The Contenders

11 The Man Who Grew Too Much - S25

I laugh so hard at the end when bob jump off the dam
Bob : oh yea I forgot I got gill too lol

Hello, it's a little lonely down here...

Meh this one is ok for a sideshow bob episode. But could get a little repetitive if watched too much - Harri666

Rake at the bottom of the 💦!

12 Day of the Jackanapes - S12

Bob brainwashes Bart to kill Krusty - CrowdedChisel

Sideshow Bob's greatest nemesis: Bart Simpson, or rakes.

This episode reminds me of star wars.Bob want Bart to joined dark my second favorite episode of Bob.

13 Who Shot Mr. Burns? Part Two - S7
14 The Telltale Head - S1

Bob first appears in this episode. But he is not in it much and does not try to kill Bart.


15 Bart Gets an F - S2
16 Treehouse of Horror V - S6
17 Bart the Murderer - S3
18 Treehouse of Horror XXVI - S27

Come on he actually killed Bart "Those bastards know how to party" was funny and Homer killed Bob!

It would been more interesting if Sideshow Bob had become Bart Simpson. Meaning he stole Bart's identity, DNA, appearance, and everything that is Bart related material. That would been quite freakish.

19 Gone Boy - S29

This time, Sideshow Bob also tries to kill Milhouse Van Houten.

20 Itchy & Scratchy & Marge - S2
21 Stark Raving Dad - S3
22 Lisa's First Word - S4
23 Another Simpsons Clip Show - S6
24 Bart the Fink - S7
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