39. Springfield's Most Stylish Criminal
"Homer the Vigilante"
Season 5, Episode 11
We don't always give old dudes the respect they deserve when it comes to style, and Springfield retirement home resident Molloy reminds us why we should respect our elders' steez. Dipped in all-black-a'thing, the cat burglar is as sleek as the animal his profession is named after. Just goes to show that, if you have the skills and the steez, you can outsmart an entire town full of dim-wits and yokels.