Occupation: Comedian
Approximate Weight: 350+ lbs.

For a guy who complained about getting no respect, he sure deserved it for his sense of style. Dangerfield wasn't afraid of going bold or cavorting around in shorts and boxers. While he looked good in a suit, he was known for looking kind of stressed, always with the top button undone and a loosened tie. In his later years, he might care less, but he still looks unintentionally cool. Only he could rock a khaki jacket, shorts, and loafers on the red carpet but keep it together with a Barneys bag as an accessory.