Kiefer Sutherland is still crazy, wore a dress on ‘The Late Show’

Kiefer Sutherland showed up on The Late Show last night… wearing a dress. Yeah. I didn’t see the huge deal about it, because let’s face it, Kiefer is kind of crazy (but still kind of hot), and wearing a dress on Letterman isn’t even in the top ten (get it?) dumb things Kiefer has ever done. Anyway, Kiefer wore a dress because he lost a bet. Because I hear that gambling is a really good way to kick alcoholism, right, Kiefer?

Gamblers beware: losing a bet can make you look foolish. Just ask Kiefer Sutherland.

The hard-core action star of Fox’s “24” sat with David Letterman on the “Late Show” Wednesday night dressed in a hideous peacock-inspired dress after losing a bet to a buddy.

“I lost a bet over the weekend,” he told Letterman, the embarrassment displayed clearly on his face. “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’.”

The Patriots lost to the Baltimore Ravens on Sunday, 33-14.

“And so, here I am,” he noted, sheepishly.

Sutherland, who gets credit for going through with the bet, accessorized the dress with combat boots and a long-sleeved white t-shirt.

Letterman offered the 43-year-old actor $1,000 to wear the outfit on the subway.

“Riding the subway would be easier than what I’m going through right now.”

Although the conversation eventually turned to Sutherland’s return as Jack Bauer on “24” this Sunday, the dress made serious conversation impossible.

“This may be the most humiliating moment of my life,” Sutherland said with a smile. “And I’ve had quite a few to choose from.”

At the end of his segment, Sutherland ran off stage as band leader Paul Shaffer played him out with Aerosmith’s “Dude looks like a lady.”

[From The NYDN]

I could be going too hard on Kiefer, but I lecture because I love. I love him and his father, I think they’re both amazing actors, and it pains me a little that Kiefer has such a screwed up personal life. By the way, if you think the dress is bad (which it is), check out what Kiefer wore to the studio – a swear, this is a denim suit. I spent too much time looking at the cut of that jacket, and that bitch is tailored like a suit jacket. Kiefer actually picked that out for himself, you know he did. That boy isn’t right in the head.

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Kiefer Sutherland outside of the Ed Sullivan Theatre on January 13, 2010. Credit: WENN.

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38 Responses to “Kiefer Sutherland is still crazy, wore a dress on ‘The Late Show’”

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  1. Roma says:

    Kaiser, because you are from the south I’ll educate you: Kiefer is rocking what we like to call a Canadian tuxedo.

  2. Kaiser says:

    Roma – Right? That’s what good ol’ boys wear to their court dates and weddings and sh-t.

    Ah, the South.

  3. lilred says:

    Kaiser in Canada we call them our denim tuxedos. Lol. Keifer is a cazy Canadian.

  4. lilred says:

    Oops,Roma me on the jump.

  5. Praise St. Angie! says:

    funny…in NJ, we call that a “guido tuxedo”. (or “zhay on zhay”…as in, J on J with a French accent.)

    I love Kiefer, too. he has his share of problems (mostly with alcohol), but he comes off as a nice guy who would be a good friend. He also doesn’t try to minimize his very public problems – he acknowledges them, which is (in a strange way) admirable.

  6. Firestarter says:

    Love Kiefer!

  7. Phowie says:

    That jacket looks prison issue to me.

  8. Oi says:

    “Me and Jay Leno in the closet”! LOL. I love him love him love him. He looks so embarrassed!

  9. alex says:

    LOL!!! Kaiser, I agree. I love Kiefer, think he is hot and sexy and love 24 but he is crazy too and I find that hot lol

  10. archiepelago says:

    Personally I love him more for not welching on the bet, lol

  11. Kiki says:

    I watched this too and I wishes the interview had lasted a little longer. After that I was surprised when Keri Russel was the next guest. I had always liked her but she seemed very defensive… I was disappointed

  12. Tia C says:

    That was cute and funny. He seems very down to earth. I wonder why he made that comment about being in the closet with Jay Leno (?!?) Are there rumors about Jay’s orientation? I’ve never heard of any. That was an odd comment.

  13. danielle says:

    I love Kiefer! However, he looked better in the dress then in that denim monstrosity!

  14. pixiegirl says:

    Denim monstrosity indeed, danielle. Does anyone else think that his pointed boots and boot-cut pants are girlie? I know they are supposed to be cowboy-ish but they look lady-like to me.

  15. Mari says:

    I thought he was pretty funny. He seems to not take things too seriously, obviously. Great trait in my book.

    Btw, I’m really diggin those jeans, and they look about my size…

  16. Hot dang, look at that denim insanity. Good thing he wore a dress then. Haha

  17. SolitaryAngel says:

    I love me some Keifer! He can do almost no wrong in my book; and I’ve always thought Leno was gay, imho.

  18. archiepelago says:

    I used to live next door to a girl that was dating him and apparently he was a gentleman. Often brought his daughter on play dates with her kid (I think his kid was a teenager at the time) and was very down to earth.

    But seriously, how can you not love this guy when you read this (from Wikipedia):

    During the autumn of 2001, Sutherland unintentionally interrupted the filming of the premiere episode of an online series titled, The Lonely Island. In the episode, “White Power,” the main characters develop an addiction to teeth whitener, and eventually mug an old woman to facilitate their addiction. Sutherland, driving by at the time, believed the mugging was real and jumped out of his car to intervene. A small portion of Sutherland’s appearance is displayed after the credits, though the portion is only Kiefer stopping his car and looking at them. This anecdote was recounted by actor Andy Samberg during an appearance on Late Night with David Letterman.

  19. d says:

    perhaps I’m a little on the perverted side, but I have no problem with a hetero guy in a dress. it’s kinda a turn on when the guy carries it off pretty well…

  20. Jen says:

    Love Keifer. I’m glad others know of our Canadian Tuxedo… when it gets this cold in the winter you get a little crazy with clothing. HAHA.

  21. LolaBella says:

    Love me some Kiefer and he just keeps getting sexier the older he gets.

    He was a really good sport to follow through on the bet; he was clearly so uncomfortable and sheepish. It was cute! 😉

  22. Sumodo says:

    Canadian tuxedo, eh? I have jeans and a denim shirt on right now, just like I wore in high school. I dare anybody to tell me I don’t look good. ‘Cause I am SMOKIN’ in my denim. Good old Kiefer, keepin’ in real.

  23. jen says:

    Oh man, I’m Canadian & forgot ALL ABOUT the Canadian Tuxedo. Shame on me! Thank you for reminding me Roma – AND NEVER AGAIN shall I forget *solemn face*

    LOL (for real, can’t stop laughing lolol) 😀

  24. jule says:

    Dont forget for us canadians that a mack jacket is a formal dinner coat as well LOL.

  25. Karen says:

    @18. OMG thanks for reminding us about that story where Kiefer thought he was saving the day. I already have my monogrammed Mrs. Sutherland tea towels on order but my love for him grew deeper when I saw Andy Samberg on Letterman relaying that story.

    On another note, I love how many fellow Canadians are avid Celebitchy readers 🙂 And that we would all cut each other fighting over Kiefer!!

  26. lastwordlinda says:

    Don’t forget, Keifer’s mother, Shirley Douglas is a Canadian actress and very good. And, I too, am amazed at the number of my fellow Canadians that read Celebitchy. We have such good taste n’est pas? Or should I say “eh?”

  27. AlaskaJoey says:

    I know that look as “Texas tuxedo”. He’s still awesome, even if he is poorly dressed.

  28. GatsbyGal says:

    At least he’s got a reason for wearing the dress…that’s not as crazy as just showing up randomly in one and offering no explanation.

  29. Kylie says:

    Cute!! Good on him for going through with it! Love it!

  30. ccoop says:

    OMG, I love him so. “Dude looks like a lady”! Priceless.

  31. Jazz says:

    Love me some Kiefer! Dress or no dress.

  32. Maritza says:

    I don’t think the denim suit looks that bad, the dress however…
    I love Kiefer he seems like a real down to earth kinda guy.

  33. kj says:

    Amazing…up north we always referred to that one as the Thunder Bay Tuxedo and, I can assure you, it’s still a frequent sight!! Glad to know it’s so popular in the rest of Canada too 😛

    Kiefer is looking more like Donald every day and it warms my heart. I just love the Sutherlands 🙂

  34. alford says:

    i don’t see what the big deal is about wearing the dress. kind of lame he’s so embarrassed about it, to be honest.

  35. Liviania says:

    @Alaska Joey: A Texas Tuxedo is a suit jacket and shirt worn with black jeans.

  36. jame says:

    That’s a barn jacket. Check llbean, cabela’s, carhartt or similar.

  37. Teri says:

    I love the man no matter what he’s wearing…my preference…nothing! Where can I see a pic of that??

  38. Hello, just wandered by. I have a Carhartt site. Truly more information than you can imagine on the web. Wasn’t exactly what I was looking for, but very nice site. Have a great day.