Jay Leno Shares Regret Over Allowing Jimmy Kimmel to ‘Humiliate’ Him: “It Was My Mistake”

Jay Leno is reflecting on the infamous moment that ignited a years-long feud with fellow comedian Jimmy Kimmel.

In 2010, Kimmel made appearances on The Jay Leno Show where he made repeated jokes at Leno’s expense regarding the Conan O’Brien and The Tonight Show shuffle.

Recently, Leno, now 64 years old, delved into that incident during an episode of In Depth With Graham Bensinger, expressing remorse and clarifying his decision not to cut out Kimmel’s barbed comments from the show.

“When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it,” Leno recalled.

Leno reflected, admitting, “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 Bensinger asked, “Why didn’t you?”

Leno responded, “Because it happened. It’s real — it happened. It’s my mistake. That’s how you learn.”

Bensinger then questioned whether the choice was still a “mistake,” noting that the moment made for compelling television. But Leno disagreed.

“It’s not good TV for me because it started a whole thing that continues to this day, really,” he said. “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 tension dates back to NBC’s messy handling of The Tonight Show succession plan. In 2009, Leno stepped down so Conan O’Brien could take the reins, while Leno moved to a new primetime series, The Jay Leno Show.

However, after both shows struggled in the ratings, NBC proposed shifting Leno back to late night and moving O’Brien’s show to a later slot. O’Brien refused the change and ultimately left the network, clearing the way for Leno’s return to The Tonight Show.

The move sparked public backlash, with many siding against Leno — including Kimmel, who voiced his disapproval during a memorable appearance on Leno’s show in 2010.

During a segment where Leno asked about the best prank Kimmel had pulled, the comedian quipped:

“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.”

Earlier this week, Kimmel revisited the subject during an episode of Jimmy Kimmel Live! as he welcomed Ben Affleck to the stage.

“You have that look on your face that you sometimes have when I see you, where you’re like, ‘What is he gonna do? Is he gonna do something?’”

“I’m not going to do anything,” he said to Affleck before joking, “It’s not going to be like when I came to your house for Christmas, and I walk in the door and then Jay Leno walks right in after me and then we’re both uncomfortably making small talk with you and you go, ‘Oh yeah, you both have something with each other?’ and then I had to stay in there.”

Affleck, somewhat amused, replied: “Believe it or not, I didn’t follow the nuance of your gossip history.”

To which Kimmel shot back: “No, you just dropped a grenade right on us.”

Affleck remembered the awkwardness of the moment well: “It was like, ‘This is painful enough. What’s weird? Is something weird? Have you guys been insulting each other publicly for decades?’”

Despite the public barbs that continued long after the 2010 incident, Kimmel revealed in a 2017 interview with The Hollywood Reporter that he and Leno eventually patched things up.

“Jay and I have made peace. After my son had his operation, he called me and he was very nice.”

Kimmel’s son, William John, now 8, was born with a heart defect and needed emergency surgery shortly after birth.

Kimmel also explained that his animosity toward Leno initially stemmed from his admiration for David Letterman. Letterman had hoped to succeed Johnny Carson as The Tonight Show host in 1993, but when NBC chose Leno, Letterman left for CBS — a move that left a lasting impression on Kimmel.

“You have to remember how much I love David Letterman. When all that stuff happened, I was just a fan, reading Bill Carter’s book [1994’s The Late Shift: Letterman, Leno, and the Network Battle for the Night.] and there was a villain and a hero, and Dave was the hero and Jay was the villain. I started off with a negative feeling about it. I sometimes insert myself into situations I have no business inserting myself into.”

Still, he admitted that Leno’s thoughtful gesture softened his views. “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.”