Kiefer Sutherland Dresses Like a Woman for David Letterman

By PopEater Staff Posted Jan 14th 2010 07:03AM

David Letterman took a little break from skewering Jay Leno and NBC last night and had Kiefer Sutherland as his guest on 'The Late Show,' who came out wearing a green dress.

"I lost a bet," the '24' star explained to a laughing audience and a shocked Dave.

"Over the weekend I was so sure New England was going to win that I told a guy who used to be my friend that if New England lost I would wear a dress on 'Letterman,'" he added, referring to the Patriots' loss to the Baltimore Ravens.

Letterman describe the frock as "quite slimming" when Sutherland twirled around to show the full effect. Watch Video After the Jump

But don't worry, before Sutherland came on, Letterman got a Conan vs. Jay joke in. "Isn't it lousy cold outside today? You know, they say, from the weather bureau, they say it's caused by an Arctic chill between Jay and Conan."

Tags: conan obrien, david letterman, jay leno, Kiefer Sutherland, TheLateShow

Comments

(20)

Thursday 14 January

By phurbee951

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Letterman is a jackass.

By Brett Bundy

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Did you even watch the show? Letterman spent most of the show mocking NBC executives, calling them idiots, mouth-breathers, and some other really funny insults, ripping apart CEO Jeff Zucker with his ugly bald picture on screen, and saying his first career choice was jockey but he was too small. The Sutherland segment was mildly entertaing, but Letterman really let it rip.

By cj

I watch some of the show and thought Dave was very mean and I went on to the Jimmy Kimbel show I found that more entertaining then both Conan who whinned and David who said see you should have kept me there, Jimmy just got another fan for his show

By Steph

I think Kiefer showed a lot of class to honor the bet he made with his friend...it takes real guts for a guy to show up on national TV in a dress!

By maria

i absolutely agree with you!!!

By John

WHY ?

By jbjg24m

takes a real man to do what he did !

By Gina

Way to go Kiefer! You showed real class in honoring your bet. I don't know anyone who would do that. Many talk the talk, but refuse to walk the walk. I didn't watch the show last night because I can't stand Letterman, and I send my thanks to popeater for posting the video clip. I look forward to watching 24 as I do every year.

By Donna

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Kiefer looks good in anything...

By scottishmedium

Keifer is a good Irish name and sutherland Scottish the way to
go what a good sport as a top medium Britain and U.S. I predect
all kinds of parts being offered to this young man he has class,
spunk, and a great sense of humour go for it Keifer and a Happy
New Year I 'see'

Thursday 21 January

By christina

hahahaha!!!! It takes a real man to wear a dress on national television. You looked great Kiefer!! ;)

By Raven Maniac

That'll teach him to bet against the Ravens........

By buddy

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I can't believe that Letterman is still that bitter about the whole NBC Tonight Show thing. He just can't let it go to this day. I'd say he did OK. Did not like to see Kiefer Sutherland in a dress. Don't care if he lost a bet, or not-it was stupid. You could tell that it made Letterman even madder than he already was. I would say that you won't see Kiefer on his show for a while.

By MiserblOF

Sutherland looks a bit like Ann Coulter in that dress..

By rej

kiefer, you're such a good sport! we're excited to see you soon @ "24" man!!!

By MSF

WELL, JACK BAUER NEVER LOOKED SO TRIM. I'M SURE KIEFER IS GLAD THAT'S ALL HE BET. AND SINCE DAVE WAS AGROCERY WORKER, AND FORMER WEATHERMAN, HE COULD APPRECIATE KIEFER'S JOKE. PERSONALLY, I'M STILL LOOKING OVER MY ON GOING ANSCHUTZ MADISON MINE CASE. I'M VERY SURPRISED TO SEE THAT SOLOMAN JEROME BRAY NOTE PAID IN THE MID NINETIES TO MR. BRAY IN VALENCIA, CALIFORNIA (THROUGH LAWYER FULTON) IS THE AREA IN WHICH MARIA FREITAG EATON RESIDED. ANY THOUGHTS, ON THIS "24" DILEMMA?

By Vic

Hey a bets a bet takes a big man to man up to it

By jackie

It KILLS me how everyone makes such a HUGE DEAL whenever a male (celebrity or otherwise) dons a dress in public. I'm sure no one would say boo if Angelina Jolie showed up on the Letterman show wearing a tuxedo, or even 501's and a T-shirt with work boots. But just put Keifer Sutherland in a dowdy frock without some much as added mascara and watch what happens. Talk about a double standard.

By Praise the Lord

You are jaded if all you see is a guy in a dress!It really IS nice to see a man keep his end of a bargain, even though no one but he and his friends knew why when he walked out onstage in that dress. Why I'd love to meet a man who would do this-it'd mean I could trust him and actually enjoy him instead of wondering, questioning his integrity! The gesture spoke volumes about his character; he's a good sport and a man of his word!

Wednesday 27 January

By tangilct

Keifer is awesome. He didn't lose an ounce of masculinity by just holding up his end of the bet. Moments like this just make me an even bigger fan of his.

10 Years from now, we'll be making Keifer Sutherland jokes instead of Chuck Norris ones.

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