By Dustin Rowles | News | July 29, 2025
Why are we talking about a late-night talk show host who retired over a decade ago from a genre of television that’s practically on life support? Great question. Mostly because Monica Lewinsky — who was 22 when she had an affair with 49-year-old Bill Clinton — recently called out Jay Leno for relentlessly mocking her in the ’90s. As she told Alex Cooper on the Call Her Daddy podcast, she made Leno’s top 10 list of targets during his time on The Tonight Show, and was the only non-public figure on it.
For whatever reason, Leno felt compelled to defend himself — not directly, of course, but by laundering statements to TMZ through “sources close to Leno.” These sources (who are clearly Leno) insisted that he didn’t target Lewinsky; she was just “an easy punchline,” which sounds… exactly like something Leno would say. “I humiliated a young woman near-nightly for a decade because it was easy!” According to the source, it wasn’t unfair, just collateral damage. “Sometimes in comedy, people get hurt.” It was all part of the late-night rivalry, he added.
Leno also sees no need to apologize because all the male hosts were doing it and, hey, it was a different time.
That is true: it was a different time, and yes, all the male hosts were doing it. But here’s the thing — some of them realized they were wrong. David Letterman, for instance, apologized over a decade ago, calling it one of his biggest regrets as a late-night host. He acknowledged that he played a role in pushing “the humiliation to the point of suffocation,” and that yes, it was unfair. “She was a kid. She was 21, 22…”
Leno, meanwhile, doesn’t understand why Lewinsky is still bringing it up. But — and this is important — he (via his “source”) wants everyone to know that he “holds no ill will against” her.
And thank God for that. Jay Leno doesn’t expect an apology from her. How magnanimous.