The Simpsons: 10 Best Villains Ever
8. Jack Crowley
It might seem a little bit rich to excuse Snake from the list but keep in Crowley, who we first meet when he’s in jail for shooting Apu. However, the Michael Keaton voiced character did a lot more than that, so he’s earned his spot in Springfield’s rogues gallery.
A talented painter who Marge meets while teaching an art class at Springfield prison, he’s released on bail shortly after, on the condition that he live with Marge and the rest of the family. She lies to get him a job painting a mural at the elementary school, and things fall apart from there.
He first paints an (admittedly awesome) mural of a Xena like figure riding a puma, but Skinner orders him to paint over it and go more ‘cutesy-wootsey’. He does so, but at the unveiling lights it on fire, almost burning down the school and damaging Skinner’s car.
He also has one of the most tonally awkward senses of humour of any character in the show’s history. He tells Marge he’s going to pray then ‘jokingly’ asks which way Mecca is, and wonders if the Mr Universe contestants can be gay because ‘they look pretty strong’. They just don’t land.