Team: Chicago Bears
Dresses like: A beaten man who has unequivocally given up on life 

Jay Cutler hates that he's good at football. He wishes he could just be a shift manager at Outback Steakhouse, but he can chuck a pigskin 70 mph through double coverage so he's tortured by a career in the NFL. When you consider his pained existence, Cutler's reasons for dressing like a deranged lunatic on bath salts become crystal clear. He'll get sacked 40 times this season and go home to the hottest girl from Laguna Beach, so what's the point of trying?