The Simpsons: 10 Best Villains Ever

Springfield’s resident mobster is arguably in the same category as the likes of Snake as an ever-present bad guy as opposed to a villain in any real story, but in early appearances especially, he tangles more directly with the Simpsons family.

We’ve seen Bart brought into the mob, Lisa befriending his cookery loving son Michael and Marge working as an interior designer for his brothels. Homer is more often used for spot gags though he’s also featured in one of the dumbest (yes, including Armin Tamzarian) storylines the show’s ever done.

The Fat Tony in the most recent seasons is not the original Fat Tony; he died in the Season 22 episode Donnie Fatso. He was then replaced by his cousin, Fit Tony, who took his place and ended up overeating, thus becoming Fat Tony. Why? Only the writing staff really know.

That incredibly surreal blotch on his record aside, Fat Tony often adds menacing depth to the stories he’s in. The earlier, more realistic tales of the show especially brought out his villainous edge, but the humour was always there too. Lines like ‘what’s a truck?’ and his gang’s pursuit of Krusty’s debt are both firmly established in Simpsons folklore.