Jay Leno Breaks Silence on Jimmy Kimmel’s On-Air Takedown: “It Still Stings After All These Years”

Fifteen years later, Jay Leno still remembers it clearly—the night Jimmy Kimmel stepped onto The Jay Leno Show set, armed with cutting jokes that would become one of late-night TV’s most unforgettable moments.

In a new sit-down with In Depth With Graham Bensinger, Leno finally opened up about the experience, calling it one of his biggest career mistakes. And despite the years gone by, the memory remains bittersweet.

“I Let It Happen”

“When Kimmel came on my show and humiliated me on my own show, I let it happen,” Leno said, his voice carrying the weight of regret. “I didn’t edit it out. It was my mistake. I trusted somebody.”

Leno, who built his career on sharp wit and impeccable timing, explained that he could have easily cut the segment before airing it. After all, it’s common practice for shows to edit out uncomfortable moments. But he chose not to.

“I thought, ‘It’s real—it happened.’ It’s my mistake. That’s how you learn,” he said, emphasizing that he wanted to own the awkward encounter rather than pretend it never occurred.

A Brewing Rivalry

The tension between Jay Leno and Jimmy Kimmel was no secret back in 2010. The infamous late-night shuffle—where Conan O’Brien briefly took over The Tonight Show before NBC reinstated Leno—left many in the industry fuming. Among them was Kimmel, who felt Leno had acted selfishly during the transition.

In what would become a legendary appearance, Kimmel went on The Jay Leno Show and unleashed a brutal jab. When asked by Leno what his best prank was, Kimmel smirked and said:

“I told a guy that five years from now I’m going to give you my show, and then when the five years came, I gave it to him… and then I took it back almost instantly.”

The audience roared, but Leno sat stunned. It was a moment that shifted the dynamic between the two hosts—and late-night television—forever.

A Warning Ignored

In hindsight, the ambush shouldn’t have been such a surprise. Just days earlier, Kimmel had openly mocked Leno on Jimmy Kimmel Live, even dressing up as Leno with a prosthetic chin and a gray wig. Standing in front of his audience, Kimmel joked:

“I’m Jay Leno, and let it hereby be known that I’m taking over all the shows in late-night!”

Despite the clear warning signs, Leno allowed Kimmel onto his stage, thinking the appearance would be a lighthearted exchange between two industry giants. Instead, it became a moment Leno would later call “painful but important.”

Kimmel’s Side of the Story

Jimmy Kimmel has never expressed remorse for what happened. In a 2012 interview, when asked about his feelings toward Leno, Kimmel didn’t hold back:

“F— him.”

Still, over the years, there have been efforts to patch things up. After Kimmel’s infant son underwent open-heart surgery in 2017, Leno reached out personally. That gesture seemed to thaw the ice—at least temporarily.

“Jay and I have made peace,” Kimmel confirmed in an interview that year. “He was very nice during a tough time.”

An Uncomfortable Reunion

However, full reconciliation might still be out of reach. Earlier this week, Kimmel recounted a recent run-in with Leno at Ben Affleck’s Christmas party. As Kimmel told the story on his late-night show, he described an awkward moment when Affleck, unaware of their complicated history, casually remarked, “Oh yeah, you both have some thing with each other, right?”

Both comedians were left uncomfortably making small talk, with Kimmel joking that Affleck had “dropped a grenade” right into their reunion.

It was a reminder that, while public wounds may scab over, the scars often remain beneath the surface.

Lessons Learned

Reflecting on the 2010 incident now, Leno insists he’s made peace with it—but he’s clearly still processing the experience.

“It’s not good TV for me because it started a whole thing that continues to this day,” he said. “I wouldn’t have done it, but that’s OK. That’s alright. It is what it is.”

Even so, Leno believes the mistake taught him a valuable lesson about trust, vulnerability, and professionalism in a cutthroat industry.

“You’ve got to own your mistakes,” he said. “You can’t blame somebody else. It was my show. It was my decision. And I’ve lived with it.”

Legacy Over Ego

Despite the painful memory, Jay Leno’s career remains one of the most successful in late-night history. With multiple Emmy Awards, bestselling books, and a second act in car restoration shows, Leno has nothing left to prove.

And perhaps that’s the ultimate takeaway. In a business often fueled by ego, Jay Leno chose humility. Instead of erasing an embarrassing moment, he allowed it to air. Instead of retaliating, he turned the other cheek.

It might not have been the easy path—but it was, in Leno’s words, “the right one.”

Looking Ahead

Today, Leno continues to focus on the things he loves: family, friends, and classic cars. And if he runs into Jimmy Kimmel again at another party?

“Well,” Leno says with a grin, “I’ll just bring a helmet—just in case.”