2. Adam Sandler

For a man who hasn't strayed from hockey jerseys and sweatpants publicly since 1994, he gets some credit for consistency. That's why he's #2 and not #1. We get it, he's the funnyman who makes a fashion statement by making an anti-fashion statement, but when you're worth $300 million, one would think you'd bother to invest in a proper suit, maybe if only for the red carpet. But hey, the guy made Jack and Jill, so his quotient for giving a fuck is evidently sub-par.