It's the first day of the PopSugar 100 bracket, and we're so excited to see how you're voting! We already have some big surprises like newcomer to the list Jon Hamm putting up a good fight against Jessica Simpson. Plus, Jay Leno and David Letterman are locked in yet another battle. Make sure to cast your votes for a chance to win a Chanel bag — and click here to start voting. Check out today's hottest head-to-heads!