Jay Leno Regrets Letting Jimmy Kimmel Humiliate Him After Conan O’Brien Takeover

When the dust settled the second time, the same man was standing there with egg on his face … again. Only this time, Jay Leno admits that at least some of that egg is his own fault.

In a recent appearance on In Depth with Graham Besinger, Leno looked back at the whole debacle, and one of the most shocking moments to come out of it, which was when Jimmy Kimmel basically humiliated him on his own show.

That moment went down in 2010, shortly after Leno’s return as host of The Tonight Show, replacing his successor Conan O’Brien after less than a year. Yeah, it was messy.

“When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it,” Leno said of the instantly viral takedown. “It was my mistake, I trusted somebody.”

“I went, ‘Ah, I made a mistake. Ok, I should pay the price,'” Leno said of the browbeating he took from Kimmel over the mishandling of O’Brien’s brief tenure. “And it’s fine, it’s fine. I mean, we could have edited it out of the show.”

Talking to him via video chat, Leno asked Kimmel his best prank, and the Jimmy Kimmel Live! host shot 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.”

And that was just one burn.

Leno explained to Besinger that he let the jokes land because “it’s real — it happened. It’s my mistake. That’s how you learn.”

Now, though, he kind of wishes he’d handled it a little differently. “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 gotta do.”

“I mean, I wouldn’t have done it, but that’s okay. That’s alright,” he added. “It is what it is.”

With the late-night hosts all so chummy these days, it’s hard to imagine how contentious things used to be, if you weren’t there. Thanks to the dominant popularity of Johnny Carson’s 29-year tenure at The Tonight Show, it was a very, very coveted position.

The first late-night war, of course, came with Carson’s retirement in 1992. David Letterman, the presumed frontrunner to take the desk as he’d hosted Late Night right behind it, was stunned when Jay Leno was announced instead. Letterman would jump ship to CBS and launch his own Late Show opposite Leno.

Jump ahead nearly 20 years and the stage was set for the second skirmish, which again found Leno in the center position. This time, it was Leno who was looking to retire.

Hoping to avoid a repeat of the Letterman disaster, he announced Conan O’Brien, who was then hosting Late Night just behind him, as his successor. He then stepped down as agreed on May 29, 2009 while still at the top of the ratings.

But he wouldn’t be gone long, and things were about to get even uglier than the Letterman debacle.

O’Brien picked up the reins and got to live his dream as Tonight Show host from June 1, 2009, but it would prove extremely short-lived. Almost immediately, there was apparent concern from NBC about ratings declines from Leno’s popular tenure.

But rather than give O’Brien time to find his voice and his audience in this new timeslot, NBC made the unexpected decision to bring back Leno — in a nightly prime-time talk show to air basically right before O’Brien’s Tonight Show (with local news between).

Suddenly, after waiting years to be the lead person in late-night, O’Brien found himself running second again to Leno, after The Jay Leno Show premiered on September 14 at 10 p.m. ET and ran nightly thereafter.

After ratings for both shows continued to decline, the network floated putting a shortened half-hour Jay Leno Show on at 11:35 p.m. nightly, which would have bumped The Tonight Show to 12:05 p.m.

But when O’Brien balked and refused to do this, the network reached a $45 million settlement with him and cut him loose, setting the stage for Leno’s return as Tonight Show host — at 11:35 p.m. nightly.

Leno would then continue as host of The Tonight Show until he retired for good in 2014, and this time offered a truly seamless succession to then-Late Night host Jimmy Fallon, who continues hosting The Tonight Show to this day.

Like Letterman before him, O’Brien took his talents immediately to another network, launching Conan on TBS in November 2010 and continuing there until 2021. He currently hosts podcast series Conan O’Brien Needs a Friend and spinoff Max series Conan O’Brien Must Go.

Leno most recently hosted Jay Leno’s Garage and the You Bet Your Life revival, while he also spends a lot of time showing off his massive car collection.