The David Letterman Cheating Scandal Explained

Today, hallowed TV personality and beard aficionado David Letterman might seem like jovial and caring host on his conversational talk show "My Next Guest Needs No Introduction." His interviews on that Netflix series have made everyone from Kim Kardashian to Will Smith get emotional and spill their guts. But from 1982 to 2015, he was known as the curmudgeonly, sarcastic late-night host with a caustic attitude, first of "Late Night with David Letterman," and later of "The Late Show with David Letterman." Even many of his guests, especially the women, found him to be rude, and off-putting.

Case in point, Cher once called him an "a**hole" right to his face, live during a broadcast in May, 1986, per Rolling Stone, and then Shirley McClaine did the same thing in 1988, per Showbiz CheatSheet. In 1994, Madonna accused Letterman of constantly ridiculing her and speculating about her private sex life on the show, and ended up cussing a reported 14 times during her infamous appearance, per Yahoo. In 2021, Paris Hilton revealed that she felt Letterman was purposefully trying to "humiliate" her with his "mean" line of questioning during her 2007 appearance, per TooFab. Many felt his approach to both Linsday Lohan and Jennifer Aniston was inappropriate.

All of these ongoing issues came to a head when Letterman revealed he was the target of blackmail, and it was all because he cheated on his wife.

David Letterman admitted on air that he cheated on his wife

On October 1, 2009, David Letterman used an entire segment of "The Late Show with David Letterman" to publicly admit that he cheated on his wife Regina Lasko mere months after they had married in March. The soliloquy from behind the desk was anything but funny, as he went into detail about finding a threatening package in the back of his car that accused him of doing "terrible things" and a blackmail plot that unfolded thereafter. 

"What was all this creepy stuff?" he said. "I have had sex with women who work for me on this show. My response to that is yes, I have. I have had sex with women on the show. Would it be embarrassing if it were made public? Perhaps it would ... especially for the women." The blackmail plot threatened to expose Letterman's secret in a film script unless he paid $2 million. Letterman then foiled the plot by giving testimony to a grand jury, resulting in the arrest of Robert J. "Joe" Halderman, who was a fellow CBS employee and the partner of Letterman's lover.

Years later, Letterman told Oprah Winfrey that he still can't forgive himself for cheating, and that he has no one to blame but himself. He revealed that telling his wife about his affair was the harder than revealing it on-air, and was still trying to fix it and regain her trust.

David Letterman had to issue an apology for discriminating against women staffers

On top of mistreating female guests and partaking in authority-abusing affairs in the workplace, David Letterman was reportedly also not too kind to his female staffers. In 2009, around the time that he revealed live on-air that he had cheated on his wife with some women on his staff, former "The Late Show" staff writer Nell Scovell published an essay in Vanity Fair, where she revealed that Letterman exercised sexual favoritism in the workplace, denying women staff promotions, and fostering a toxic male-dominated workplace.

It took a full decade for Letterman to read the essay, and Scovell spoke with him face to face to gauge his reaction to her allegations. "When I read that document you wrote 10 years ago," Letterman told her in 2019 in her Vanity Fair follow-up, "I just thought, There's nothing to be upset about here. It happened, that's all true." 

"I'm sorry I was that way," he continued, "and I was happy to have read the piece because it wasn't angering. I felt horrible because who wants to be the guy that makes people unhappy to work where they're working? I don't want to be that guy. I'm not that guy now, I was that guy then." It would seem, like his extramarital affair, Letterman still feels guilt over his past behavior, but Scovell didn't offer him atonement. "Dave still carries around his guilt and I still carry around my anger," she wrote.