Jay Leno is opening up about a moment he still regrets — when Jimmy Kimmel publicly called him out on The Tonight Show during the infamous late-night TV feud involving Conan O’Brien.
In 2010, tensions were high as Leno stepped back into his hosting role at The Tonight Show, a move that left Conan O’Brien sidelined after briefly taking over. During a now-famous appearance, Jimmy Kimmel used the opportunity to roast Leno directly on his own show, delivering a scathing jab that many viewers still remember.
When Leno asked Kimmel about the best prank he’d ever pulled, Kimmel didn’t hold back:
“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 pointed joke referenced the controversial 2010 late-night shuffle that saw The Jay Leno Show underperform in prime time, ultimately leading NBC to restore Leno to The Tonight Show — much to Conan O’Brien’s disappointment.
Jay Leno Opens Up About the Mistake During a Recent Interview
During the April 23 episode of In Depth with Graham Bensinger, Jay Leno revisited that uncomfortable chapter, admitting he made a crucial mistake by not editing out Kimmel’s mocking remarks.
“When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it,” Leno said. “It was my mistake, I trusted somebody. I went, ‘Ah, I made a mistake. Okay, I should pay the price.'”
When asked why he chose to leave the footage intact, Leno emphasized authenticity:
“Because it happened. It’s real — it happened. It’s my mistake. That’s how you learn.”
Though some critics hailed the moment as “great TV,” Leno confessed he never saw it that way.
“It’s not good TV for me because it started a whole thing that continues to this day, really,” he explained. “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. It is what it is.”
The Longstanding Impact of the Jay Leno, Jimmy Kimmel, and Conan O’Brien Feud
The drama between Jay Leno, Jimmy Kimmel, and Conan O’Brien has long been a touchstone in the history of late-night television. Leno’s decision to reclaim The Tonight Show after promising it to O’Brien remains controversial even years later.
Despite the friction, Leno and Kimmel eventually buried the hatchet. In a 2017 interview on The Hollywood Reporter’s Awards Chatter podcast, Kimmel confirmed that he and Leno had made peace following a personal tragedy in Kimmel’s life.
“Jay and I have made peace,” Kimmel said, revealing that Leno reached out with kindness after Kimmel’s son, Billy, underwent open-heart surgery. Kimmel even praised Leno’s career, saying, “You can’t argue with [Leno’s] success and his longevity.”
A Defining Moment in Late-Night TV History
Jay Leno’s candid reflections highlight just how defining that confrontation was — not just for his career, but for late-night TV as a whole. Even today, the saga of Jay Leno, Conan O’Brien, and Jimmy Kimmel remains one of the most talked-about chapters in entertainment history.
