21. Marlon Brando
Approximate Weight: 300+ lbs.
When it comes to fat guys with swag, Marlon Brando is a definite shoo-in. He's the fucking godfather, literally. But besides getting dappered up to be Don Corleone, he set an example for former Hollywood heartthrobs who also didn't age as gracefully. Look at guys like Jack Nicholson and Alec Baldwin, who've put on a few pounds in their twilight years. Brando stuck mostly to staples like dark suits and golf jackets, and sure, sometimes he even went casual with denim jackets and printed shirts, but when it came time to be in the spotlight or on camera, he knew how to dress for his body type.