10 Things You Didn’t Know About Sideshow Bob

Sideshow Bob is often considered to be the best occasionally-present character in The Simpsons. His devious voice (thanks to the incredible talents of Kelsey Grammer), fluffy hairstyle, and overwhelming desire to kill Bart Simpsons mean that an episode centering on him is pretty much always a winner.

We’ve gathered ten facts about Robert Terwilliger that might only be known to the biggest fans of The Simpsons.

10 He’s A Genius

You might be able to have taken an educated guess at this one based as his voice alone, but Robert Terwilliger is a genius. Well, sort of. He claims, many times, to be a genius in terms of just about everything, from crime to comedy to opera. In fairness to him, he does sing Bart an entire opera at one point.

9 He Ran For Mayor Of Springfield

After one of the many, many times Bob was released from prison, he decided to run for the position of mayor of Springfield. He is a devoted Republican, and somehow managed to beat Mayor Quimby by a huge landslide.

It might have led him straight back to prison after it was found to be a set-up, but in his time as mayor, Bob had Bart moved back to Kindergarten.

8 He Used To Work With Krusty The Clown

It is often referenced, but Bob’s time working alongside Krusty came before the timeline of The Simpsons began. The first episode we ever see Bob in shows him framing Krusty as revenge. What you may not realize if you haven’t seen that episode, is that Bob was once upon a time the equivalent of Sideshow Mel on the Krusty The Clown Show.

7 His Feet Are Huge

The idea of Bob’s massive feet is often a source of physical comedy in episodes featuring Sideshow Bob. He is shown to be forced to wear comedically large shoes, which has led to a range of different outcomes.

It ended up getting him caught trying to frame Krusty, but it also meant he was able produce excellent Italian wine because he was so good at crushing grapes. Got to use those talents when you have them, huh?

6 He Has Interesting Family Connections

We don’t see a lot of Sideshow Bob’s family, but the few episodes in which we do introduce us to a colorful collection of characters. The most interesting of these is his brother Cecil and father Robert Terwilliger Sr. They are played by David Hyde Pierce and John Mahoney respectively, who also play Frasier’s brother and father. Frasier himself is played by Kelsey Grammer, who voices Sideshow Bob! Hollywood sure is a small place, isn't it?

5 He Found An Italian Family

After being forced out of Springfield, we didn’t see or hear a lot from the town’s most famous killer. Eventually, it transpires that he had moved to a small town in Italy and settled down with a wife and child, who were pretty much as obsessed with murder (or vendetta, as their son Gino lovingly puts it) as he is. An absolute match made in heaven.

4 And Actually Did Become Mayor

Interestingly, despite the overwhelming failure of his plans to become mayor of Springfield, Bob managed to become mayor of the small Italian town he moved to.

In this town, nobody knew of his horrific crimes and creepy past life, and he was able to lead them rather well. Obviously, things changed quite a lot when the Simpsons showed up, but things ran pretty smoothly for a while.

3 He Was, At One Point, Redeemed

During one of his many terms in prison, Bob attempted to change himself, becoming a member of the Christian outreach, and being declared as redeemed by Reverend Lovejoy. This time, it was actually true, and he was an innocent man who was being framed by his own brother. He still ended up back in jail anyway.

2 He Saved Homer’s Life

For some very strange reason, the Springfield Police Department thought that the best person to track down whoever attempted to kill Homer Simpson was the man who has tried to murder Bart Simpson over and over again.

Despite this weird set of circumstances that you’d think would make Homer hate Bob quite a lot, he actually managed to save Homer’s life. Of course, he still wanted to kill Bart after all of that, but he just couldn’t bring himself to do it.

1 He Is Released As A ‘Minor’ Offender

One of the many times Sideshow Bob was re-released from prison (he has had an impressive number of prison sentences), the frizzy-haired killer was considered a ‘minor offender.’ Considering Bob is a repeat offender who has consistently tried to kill an innocent ten-year-old boy for a number of years, you’d think he’d be a little more than a ‘minor’ offender, right?

NEXT: The Simpsons: 10 Life Lessons That Are Still Applicable Today