10. Letterman Responds to Bristol Palin Joke (June 10, 2009)
Irreverent and silly Dave may be, but his brand of humor has never been particularly vicious or hurtful. Still, the host angered people when he made a joke about the Palins' trip to New York in the summer of 2009, commenting that, "One awkward moment for Sarah Palin at the Yankee game: During the seventh inning, her daughter was knocked up by Alex Rodriguez." The politician shot back, accusing him of promoting child rape. (It was Palin's 14-year-old daughter Willow who was at the game — not 18-year-old Bristol, who had given birth in December 2008.) Dave responded to the controversy, acknowledging the joke was in poor taste but clarifying that he would never make light of having sex with an underage girl. "Look at my record, it has never happened," he said angrily. "I don't think it's funny, I would never think it's funny." Letterman invited the former Alaska governor to be on the show, but she never took him up on the offer.