Jay Leno Explains Why He Let Jimmy Kimmel Roast Him Over Conan O’Brien Debacle on His Own Show

Jay Leno let Jimmy Kimmel roast him on his own show in 2010 because he believed he was to blame for the moment, which kickstarted the two late-night hosts’ 15-year, ongoing feud.

“When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it,” Leno revealed during a guest appearance Wednesday on “In Depth With Graham Bensinger.” “It was my mistake, I trusted somebody. I went, ‘Ah, I made a mistake. Okay, I should pay the price.’ And it’s fine, it’s fine. I mean, we could have edited it out of the show.”

When he was asked why he did not cut Kimmel’s famous appearance on the “Jay Leno Show,” the former “Tonight Show” host said, “Because it happened. It’s real — it happened. It’s my mistake. That’s how you learn.”

In 2009, Leno famously passed the mantle of “The Tonight Show” host to Conan O’Brien only to sign on to host his own primetime NBC show, the short-lived “Jay Leno Show,” which went on to air before “The Tonight Show.” When O’Brien refused NBC’s request to push “The Tonight Show” to 12:05 a.m. so that the “Jay Leno Show” could have its long-held 11:35 p.m. slot, he subsequently exited as host and was replaced by a returning Leno.

In the midst of that conflict, Kimmel appeared as a guest on the “Jay Leno Show” and used the opportunity to take shots at Leno to his face over his disruption of O’Brien’s planned “Tonight Show” ascension. When Leno asked Kimmel what the best prank he had ever pulled was, Kimmel sarcastically responded, “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.”

That joke was one of several Kimmel lobbed that night at Leno. Reflecting on the moment in question, Leno disagreed with Bensinger’s assertion that it resulted in good TV. “It’s not good TV for me because it started a whole thing that continues to this day, really,” Leno explained. “But it’s okay, it’s alright. He’s a comic — you do what you got to do. I mean, I would not have done it, but that’s okay. That’s alright. It is what it is.”

Leno and Kimmel’s feud has, indeed, continued to this day. In March, Kimmel responded to O’Brien’s well-received stint hosting the 2025 Oscars by joking that he had heard ABC was going to give the job to Leno in 2026. He also poked fun at Leno again when O’Brien’s TBS talk show “Conan” ended after 11 seasons in 2021. On Wednesday, Kimmel’s feud with Leno even came up while the former was interviewing Ben Affleck for “The Accountant 2.”

Kimmel told Affleck that he had nothing to worry about during his latest appearance on “Jimmy Kimmel Live!” and assured him, “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 we’re both uncomfortably making small talk with you, and you go, ‘Oh yeah, you guys have some thing with each other, right?'”

You can watch the full segment in the video above.

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