I lost a bet. Over the weekend, I was so sure New England was going to win that I told…the guy who used to be my friend that if New England lost, I would wear a dress on Letterman.” And this is a man whose word is clearly bond! Hmm, maybe a move like this could have spiced up his bland relationship with ex-girlfriend, Julia Roberts.
Dave teased Kiefer for not waxing his legs for the occasion and offered the actor $5,000 to ride the subway in his frumpy dress. I doubt this is what the talk show host really had in mind. Letterman also suggested there was no bet to begin with, to which Kiefer responded, “Me and Gay Leno in the closet? No.” Ha! My Kiefer made a funny!
We should have known something was up when Sutherland showed up for his interview in all denim and a giant, suspicious-looking duffel bag in his hand.
Watch the video of Kiefer Sutherland wearing a dress on David Letterman after the jump.