Star loses bet, pulls his most hilarious appearance to date

Jan 14, 2010 11:30 GMT  ·  By
Actor Kiefer Sutherland makes a dashing appearance on David Letterman in green dress and combat boots
   Actor Kiefer Sutherland makes a dashing appearance on David Letterman in green dress and combat boots

Thanks mostly to his part on the critically acclaimed and highly popular “24” television series, but also due to some incidents in his personal life, people perceive Kiefer Sutherland as this macho type who would knock somebody into the ground for solely looking at him the wrong way. This bad boy image was shattered the other night, when the actor put in an appearance on David Letterman in a green dress and combat boots, as the Huffington Post can confirm.

Although he’s known to do some pretty crazy things (like this one), wearing a dress while on Letterman’s popular show was not Kiefer’s idea, as he reveals only seconds after taking a seat on the couch. On the contrary, the actor explains, he had to do it because he’d lost a bet with a friend (who can no longer call himself a friend because of it) and thus owed him an appearance on the show in a dress.

However, actually buying the item was the most horrible part of the experience, not the humiliation of appearing like that on television, the actor further says. Going into a women’s store, inquiring about a dress for a “heavy girl” with a broad chest and then asking if he could try it out would certainly make the list of Sutherland’s most embarrassing experiences ever, he explains. Letterman joking about his forgetting to shave or match the dress with stockings and heels certainly did not help to make the actor more comfortable, as the funny video below shows.

“Kiefer Sutherland wore a dress on Letterman Wednesday night, much to his own chagrin. Decked out in combat boots, a long-sleeved t-shirt and a green print dress, the ‘24’ star told Dave that he lost a bet over the weekend, wrongly believing the New England Patriots would beat Baltimore. But while Kiefer lost, the audience won. Dave’s first comment, when he stopped laughing, was, ‘You doing a remake of Beverly Hillbillies? You’re Granny?’ He followed up with an offer, ‘If you get on the subway like that, I’ll give you $1,000’,” the Post writes.

However, perhaps the funniest part in the interview is when Kiefer starts talking about some accident on set, where he tumbled off his horse into a river, to which Letterman, apparently very concerned and absorbed by the conversation, goes, “Wow, and did you lose your purse?” See the entire segment below. Enjoy.