Jay Leno Regrets Letting Jimmy Kimmel ‘Humiliate Him’

Fifteen years later, and Jay Leno still can’t shake the sting of getting roasted on his own turf by Jimmy Kimmel.

In a brand-new interview on In Depth with Graham Bensinger, the former Tonight Show host got candid about what he calls one of the biggest “mistakes” of his career — trusting Kimmel to come on The Jay Leno Show and not completely humiliate him. Spoiler alert: big mistake.

“When Kimmel came on my show and humiliated me on my own show, I let it happen,” Leno admitted, sounding like he still hasn’t forgiven himself. “It was my mistake. I trusted somebody.”

Flash back to 2010. Leno was trying to recover from the infamous Tonight Show chaos — you know, the mess where Conan O’Brien got the job, only for NBC to shove him out and reinstall Leno months later. Jimmy Kimmel wasn’t about to let that drama slide. When Leno asked him about the best prank he ever pulled, Kimmel savagely replied, “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.”

Ouch.

Leno had every chance to cut that moment from the show but didn’t. “We could’ve edited it out,” he said. “But it’s real—it happened. It’s my mistake. That’s how you learn.”

Honestly, maybe he should have seen it coming. Just days earlier, Kimmel went full troll mode on Jimmy Kimmel Live, dressing up like Leno — prosthetic chin and all — and announcing he was “taking over all the shows in late-night.” Zero chill.

And if you think Kimmel regretted any of it, think again. When asked in 2012 what he thought about Leno, Kimmel famously replied, “F— him.” Classy.

Despite the brutal history, there was a brief thaw in 2017 after Kimmel’s son underwent open-heart surgery. Leno reached out with kindness, and Kimmel told Oprah they’d “made peace.”

But don’t expect warm hugs anytime soon. Just this week, Kimmel told a fresh story on his show about awkwardly bumping into Leno at Ben Affleck’s Christmas party. According to Kimmel, they exchanged stiff small talk before Affleck (completely clueless) pointed out their decades-long feud like it was nothing.

“You just dropped a grenade right on us,” Kimmel joked about the encounter.

Meanwhile, Leno insists he’s “fine” about it all — even though he also confessed that the Kimmel ambush started “a whole thing that continues to this day.”

“It’s not good TV for me,” Leno shrugged. “I mean, I wouldn’t have done it, but that’s OK. That’s alright. It is what it is.”

One thing’s for sure: in late-night TV beefs, some wounds never really heal.