12 Best Male Celebrity Drag Moments: Dude Looks Like a Lady! (PHOTOS)

Perhaps the least willing celebrity cross-dresser on this list is Kiefer Sutherland, who did it not for a role, but rather because he lost a bet.

The actor appeared on The David Letterman Show March of 2010 in a horrible pale green dress, prompting Letterman to quip, “You doing a remake of Beverly Hillbillies? You're Granny?” The host then challenged Kiefer to another bet: “If you get on the subway like that, I'll give you $1,000.”