33. Fats Waller
Approximate Weight: 299.8 lbs.
Fats Waller had an iconic smile, but he was also known for the half-ashed cigarette partially dangling out of it. He essentially created Guns N' Roses guitarist Slash's signature look years before he was born. Like most jazz musicians, Waller was almost always suited up—those were just the times. But where he injected his own personality was with a rounded bowler hat and pencil mustache.