The Simpsons: 10 Best Villains Ever

The Simpsons has been around for 30 years now, and as is natural in an episodic show such as this, there’s been a whole host of antagonists for the main characters to deal with. To try and keep plots fresh (without a crazy wedding or Marge becoming a robot), new characters are often introduced specifically as roadblocks for the family to deal with.

This in and of itself is nothing new though. The characters featured here span pre and post-Golden Era (commonly thought of as Seasons 3-4 until Seasons 9-10), though a good majority did appear during that sweet spot. For all the other criticisms you can throw at the show down the years, shortage of guest stars is definitely not one of them.

Importantly, this is villains in particular; and as such they need to have done something fitting the description of villainous to earn their spot. For example, while Nelson is a bully, he’s on Bart or Lisa’s side in quite a few episodes, so isn’t really in the ballpark of evilness.

Likewise, career criminal Snake has shot Apu, sure, but there’s just a $100 fine for that these days. The ones that make the cut are much more monstrous.

Kicking things off with a post-Golden Era villain (though Gladwell is an exception, not the rule), this wacky character is a fairly on the nose Gene Wilder as Willy Wonka parody, at least at first. These sorts of off the wall weirdos tend to pop up once a Season these days, with Gladwell, Steve Coogan’s Rowan Priddis and Guthrie Frenel the hits sprinkled amongst the misses.

Gladwell pops up around midway through the episode when his comical car bumps into Bart, knocking a stack of homemade T-shirts out of his hands. Gladwell is taken by the humorous slogans and offers to go into business. Bart, enthralled by Gladwell’s ridiculousness, agrees in a heartbeat.

At first things go great, with Bart earning money hand over fist and pushing Homer into a b-plot where, usurped as the breadwinner, he dedicates himself to connecting with Maggie.

Gladwell has some fantastic moments too, like sneaking behind the family to throw leaves in their face when he ‘must be leaving’ and scurrying around on roller blades. His Dr Seuss way of talking is zip-zap-zupuluos too.

Eventually though it turns out he’s been scamming Bart, selling off the brand to Disney with his ‘loopy lawyers’ ensuring Bart gets nothing.