It’s been 15 years since Jimmy Kimmel “humiliated” Jay Leno on national television and the moment still stings.
“When Kimmel came on my show and humiliated me on my own show, I let it happen,” Leno said wistfully in a new episode of In Depth With Graham Bensinger, acknowledging one of the biggest “mistakes” of his career.
Kimmel had it out for Leno over the infamous Tonight Show debacle in which Conan O’Brien briefly took over as host before NBC ultimately reinstated Leno. Kimmel visited The Jay Leno Show in 2010 armed with the jokes he’d later call “probably my proudest moment.”
During his Kimmel’s Leno appearance, Leno asked him what his best prank was. Kimmel 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.”
The moment still leaves a bad taste in Leno’s mouth.
“I didn’t edit it,” Leno said on In Depth. “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’ve edited it out of the show,” he continued, but he opted not to because “it’s real—it happened. It’s my mistake. That’s how you learn.”
The moment could have been expected, as just before his appearance on Leno, Kimmel donned a prosthetic chin and gray wig to mock the host on Jimmy Kimmel Live, telling his audience, “I’m Jay Leno, and let it hereby be known that I’m taking over all the shows in late-night!”
Kimmel has no regrets about his relentless roasting of Leno, as he expressed in 2012 when asked for his thoughts on the host. “F— him,” he said then. Though Leno told Oprah Winfrey he felt “sucker punched,” by Kimmel jokes, the pair seemed to put their old feelings to bed after Kimmel’s son underwent open-heart surgery in 2017.
“Jay and I have made peace,” Kimmel said then. “After my son had his operation, he called me and he was very nice.”
And yet, there is at least still some awkwardness there as evidenced by both Leno’s new comments and a story Kimmel just told Wednesday night of this week about running into Leno at Ben Affleck’s Christmas party this past year.
“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 some thing with each other?’ and then I had to stay in there,” Kimmel recalled to Affleck on his ABC late-night show.
As Affleck admitted he didn’t know “you guys had been insulting each other publicly for decades,” Kimmel responded, “No, you just dropped a grenade right on us.”
It’s still just as fresh for Leno, it seems, though he insists “it’s fine,” as he said Wednesday. “It’s not good TV for me because it started a whole thing that continues to this day, really,” he explained. “I mean, I wouldn’t have done it, but that’s OK. That’s alright. It is what it is.”
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