The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best

The best bits from the bouffanted baddy.

By Josh Mills /

Picking your favourite Simpsons character is like picking your favourite yellow skinned, four fingered child. The show’s 31 years have produced endless iconic creations to pick from - it’s simply too hard.

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Most, however, would surely agree that Sideshow Bob has to be right up there. Silkily voiced by Frasier star Kelsey Grammer, the convict and former Krusty the Clown sidekick, has starred in only 15 episodes of The Simpsons (with a few additional minor appearances over the run), but has left an indelible impression on the show.

Master criminal, attempted murderer, scholar, family man - there are many strings to Bob’s bow, which have been exploited over his years of service to The Simpsons universe. He’s all but guaranteed to lift the quality of any episode he appears in.

Bob doesn’t appear as frequently as he once did - given the way the show has been going in general, it’s hard to say whether or not this is a bad thing. Just as the quality of The Simpsons has varied over the years, so has the standard of Sideshow Bob starring instalments. From the divine to the duds, this is how they stack up.

15. The Man Who Grew Too Much

The Simpsons, it goes without saying, is a cartoon. There are no two ways about it. But back in the day, it didn’t used to be so cartoony. It could break the laws of physics at times, and it used its medium to bolster its comedy. But there was a limit - it never became so silly that we couldn’t relate to it.

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Sideshow Bob genetically mutating himself so that he can unhinge his jaw like a python and swim underwater? That’s just too far! If this sounds like a family show being taken too seriously, well, it is. But at the same time, episodes like this, 25 years into the run of a show, seem like a slap in the face.

It would be alright if there were decent jokes to be derived from the farfetched setup, but there aren’t. The episode teams up Bob and Lisa, which is fresh to start with, but brings out the more tedious characteristics of both. It becomes an excuse for the writers to show off the research they’ve done on, for some reason, Walt Whitman. Kelsey Grammer remains unassailable, but even with Sideshow Bob in the mix, this is a dud.

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