Sutherland loses football-related bet , dons woman's dress

The 43 year-old Sutherland surprised Letterman when he came on stage in a hideous peacock-inspired dress. And, when asked the reason, he explained that he lost a football-related bet with a friend.

Sutherland dresses up
After seeing the actor appearing on the stage wearing a blue-green, print sleeveless wrap dress with a long sleeved undershirt underneath and combat boots on his feet, Letterman chucked and asked: "You're doing the remake of Beverly Hillbillies? You're granny? You're – what's happening here?"

"Far worse than that," Sutherland answered, "I lost a bet. Over the weekend, I was so sure New England was gonna win that I told a guy who used to be my friend that if New England lost, I would wear a dress on Letterman."

Sutherland then stood up for laughing audience and modeled his outfit.

Challenge?
The show host took it further by challenging the actor to ride the subway wearing a dress. "You ride the subway, I'll give you $1,000," Letterman said. "You get on the subway like that... downtown."

Sutherland’s reply was: "I have to say, riding the subway would be easier than what I'm going through right now. This, I think, may be the most humiliating moment of my life, and I've had a couple to choose from."

Sutherland’s segment ended with a song, Aerosmith's "Dude looks like a lady," played by a band leader Paul Shaffer, making the TV star run off the stage.

Sutherland’s professional and personal life
Born on Dec. 21, 1966 in London, UK, Sutherland is the son of actor Donald Sutherland and Canadian actress Shirley Douglas. He made a big screen debut by appearing as Bill in “Max Dugan Returns” in 1983.

Sutherland is most famous for his role as CIA agent Jack Bauer in the worldwide TV hit “24”. His magnificent acting in the Joel Surnow and Robert Cochran- created series helped him win a Golden Globe Award, a Screen Actors Guild Award, two Golden Satellite Awards, and two Emmy nominations.

Sutherland has been married twice. In 1988, he was married to actress Camelia Kath who was 14 years his senior. But their marriage lasted for only two years. The couple filed for divorce in February 1990. They share a daughter, Sarah Jude, born in the same year they got married. He was married a second time, to Kelly Winn, on June 29, 1996. Unfortunately, the relationship ended in May 2004.

The actor is known to have had romantic relationships with several women, like Julia Roberts and dancer Amanda Rice. He got engaged to Roberts in 1991, although their relationship ended just five days before their planned marriage, which was scheduled for June 14, 1991.