9. Patrice O'Neal
Approximate Weight: 300+ lbs.
Patrice O'Neal was hilarious, but never looked as funny as he was. His style was actually very similar to how rappers dress, consisting of a lot of baseball caps and leather jackets. His cap game was really on point though, ranging from patchwork suede, elephant print, and even Coogi. You can't deny that dude had taste. When he wasn't rocking an all-black outfit that would make Jay-Z jealous, he dressed up in gear like velvet or leather blazers and a simple fedora. It was clean and timeless.