Jay Leno Opens Up About Letting Jimmy Kimmel Roast Him on Live TV: 'My Mistake'

Jay Leno is taking a candid stroll down memory lane, revisiting the infamous moment when he let Jimmy Kimmel take some serious comedic swings at him—right on his own turf. Back in 2010, during an appearance on "The Jay Leno Show," Kimmel didn't hold back, poking fun at Leno for the now-legendary "Tonight Show" fiasco with Conan O'Brien.

Fast forward to this week on "In Depth With Graham Bensinger," and Leno, now 64, admitted he regrets not hitting the edit button on Kimmel's zingers. "When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it," Leno recalled, owning up to the moment. He added, "It was my mistake, I trusted somebody. I went, ‘Ah, I made a mistake. OK, I should pay the price.’ And it’s fine, it’s fine. I mean, we could have edited it out of the show."

When pressed on why he didn’t just trim the segment, Leno doubled down: "Because it happened. It’s real — it happened. It’s my mistake. That’s how you learn." Apparently, Leno's idea of learning is a little more public than most people’s pop quizzes.

Leno made it clear he never saw the moment as "good TV." Instead, he said, "It's not good TV for me because it started a whole thing that continues to this day, really. But it's okay, it's alright. He's a comic — you do what you gotta do. I mean, I wouldn't have done it, but that's okay. That's alright. It is what it is."

The whole drama originated during NBC's chaotic late-night shuffle in 2009. Leno stepped down from "The Tonight Show" for Conan O'Brien, only to get his own primetime gig. When both shows stumbled in the ratings, NBC tried to move Leno back to late night, pushing O'Brien even later. O'Brien refused, left the network, and Leno returned as host—setting off a media circus and a tidal wave of backlash. Kimmel, a self-proclaimed O'Brien supporter, came on Leno's show the next year and, in classic Kimmel fashion, called out Leno with a joke about promising someone a show, giving it to them, and then snatching it back almost instantly. Ouch.

This late-night rivalry even made its way into Kimmel's recent on-air banter with Ben Affleck, with Kimmel joking about awkward holiday run-ins with Leno. Affleck, never one to let a moment slide, simply replied, "This is painful enough. What's weird? Is something weird? Have you guys been insulting each other publicly for decades?" If only every family gathering had this kind of entertainment value.

Despite years of public barbs, Kimmel revealed in 2017 that the ice finally thawed after the birth of his son, William John, who underwent emergency heart surgery. Leno reached out with a supportive call, and the feud finally fizzled out. Kimmel credited his love for David Letterman as one reason for his original anti-Leno stance, joking about casting himself in a late-night soap opera he had no business starring in. But time—and a little empathy—seems to have mellowed everyone out.

These days, Kimmel admits, "You can't argue with [Leno's] success and his longevity. I will say, when I was in high school and college, he was one of my all-time favorite comics." Funny how a little compassion (and maybe a few decades) can turn a TV rivalry into a footnote. Late-night TV: where the grudges are just as legendary as the punchlines.