Letterman chuckled when he saw Sutherland take the stage wearing a blue-green, print sleeveless wrap dress with a long sleeved undershirt underneath and combat boots on his feet.
"It's, uh, you're doing the remake of 'Beverly Hillbillies?' You're Granny? You're -- what's happening here?" Letterman asked.
"Far worse than that," Sutherland, star of TV's "24," explained, "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.'"
"You ride the subway, I'll give you $1,000," Letterman later told the actor. "You get on the subway like that... downtown."
Sutherland laughed and replied: "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."
Celebrity Breakups and divorces of 2014 [PHOTOS]