Kiefer Sutherland is a man of words. The tough actor entered into a bet with a friend, over the weekend, that he would wear a dress on Letterman if his team, the New England Patriots, failed to beat the Baltimore Ravens. His team lost, but Kiefer won the gentleman’s crown when he actually graced the late show in a granny dress. Love you, Kiefer!
Best moment: Each time he tucks his dress between his legs!