The David Letterman cheating scandal explained

Today, hallowed TV personality and beard connoisseur David Letterman may come across as a cheerful and caring host on his talk show My Next Guest Needs No Introduction. His interviews in this Netflix series got everyone from Kim Kardashian to Will Smith to get emotional and pour out their hearts. But from 1982 to 2015, he was known as a grumpy, sarcastic late-night host with a caustic attitude, first on Late Night with David Letterman and later on The Late Show with David Letterman. Even many of his guests, especially the women, found him rude and repulsive.

Case in point: Cher once called him an “a**hole” right in his face live during a May 1986 broadcast on Rolling Stone, and then Shirley McClaine did the same showbiz thing in 1988’s CheatSheet. In 1994, Madonna accused Letterman of constantly taunting her and speculating about her private sex life on the show, eventually swearing 14 times during her infamous appearance, per Yahoo. In 2021, Paris Hilton revealed that Letterman intentionally tried to “humiliate” her with his “mean” questioning during her performance in 2007, per TooFab. Many felt his approach to 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 for cheating on his wife.

David Letterman admitted to cheating on his wife on air

On October 1, 2009, David Letterman used an entire segment of “The Late Show with David Letterman” to publicly admit that he had cheated on his wife Regina Lasko just months after their marriage in March. The monologue behind the desk was far from funny as he detailed how he’d found a threatening package in the back of his car accusing him of doing “horrible things” and a blackmail scheme that unfolded afterwards.

“What was all that creepy stuff?” he said. “I’ve had sex with women who work for me on this show. My answer to that is yes, I have. I had sex with women on the show. Would it be embarrassing if it was made public? Maybe it would be… especially for the women.” The blackmail scheme threatened to expose Letterman’s secret in a screenplay if he didn’t pay $2 million. Letterman then foiled the conspiracy by testifying before a grand jury, leading to the arrest of Robert J. “Joe” Halderman, who was a CBS colleague and the partner of Letterman’s lover.

Years later, Letterman told Oprah Winfrey that he still couldn’t forgive himself for cheating and that he couldn’t blame anyone but himself. He revealed that telling his wife about his affair was harder than revealing it on air and was still trying to fix it and regain her trust.

David Letterman has had to apologize for discrimination against female employees

In addition to abusing female guests and participating in authority-abusive affairs in the workplace, David Letterman was also reportedly not overly kind to his female co-workers. In 2009, around the time he revealed live on air that he had cheated on his wife with some women on his staff, former “The Late Show” contributor Nell Scovell published an essay in Vanity Fair, in in which she revealed Letterman coached sexual favoritism in the workplace, denying promotion to women and promoting a toxic male-dominated workplace.

It took Letterman a full decade to read the essay, and Scovell spoke to 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 her 2019 Vanity Fair follow-up, “I just thought, ‘There’s nothing to get excited about here. It happened, that’s all true.”

“I’m sorry I was like that,” he continued, “and I was glad I read the article because it wasn’t upsetting. I felt horrible because who wants to be that guy who makes people unhappy working where they work again? I don’t want to be that guy. I’m not that guy now, I was that guy then.” It seems that, as with his extramarital affair, Letterman still feels guilt about his past behavior, but Scovell offered no atonement. “Dave still carries carrying his guilt and still carrying my anger,” she wrote.