Jay Leno recently opened up about some of the most awkward and revealing moments from his long career in comedy and late-night TV. In a candid interview on In Depth With Graham Bensinger, Leno looked back on everything from performing in a Dorchester brothel to being publicly roasted by Jimmy Kimmel on The Tonight Show—a moment he calls one of his biggest televised mistakes.
Leno's Dorchester Brothel Story Shows How Far He’s Come
Before he was the king of late-night, Leno worked every odd gig he could find. One of those jobs took him to a brothel in Dorchester, where he quickly realized the audience wasn’t exactly what he’d hoped for. “I guess the girls were on the second and third floor,” Leno said. “So I walk in, I sit down, and it’s all men with lunch pails… They’re just trying to get in and out real quick, you know?”
He laughed at the misfire but didn’t shy away from sharing the uncomfortable truth. It’s the kind of story that humanizes a guy who’s spent decades in front of millions of people. Leno didn’t start at the top, and he wasn’t afraid to perform for crowds that weren’t exactly… enthusiastic.
The 2010 Kimmel Interview: When Late-Night Turned Personal
The most talked-about moment in Leno’s recent interviews isn’t a punchline—it’s a full-on throwback to the messy late-night shuffle NBC pulled in 2010. After Conan O’Brien left The Tonight Show—under controversial circumstances—Leno was brought back as host. During one of these early reinstated episodes, Jimmy Kimmel guest-hosted and used the opportunity to mock Leno.
“When Kimmel came on my show and humiliated me on my own show, I let it happen,” Leno said. “I didn’t edit it. 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.”
Kimmel’s bit wasn’t just teasing—it was pointed. When asked about his best prank, Kimmel 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.”
It was a jab straight out of a roast, but this time, Leno was the target—and it was his own show. Leno admitted he could have edited the segment out but chose not to. “I made a mistake. That’s how you learn,” he said. “I wouldn’t have done it, but that’s OK. It is what it is.”
How Leno And Kimmel’s Feud Ultimately Found Peace
Their late-night clash might have burned bright for a time, but it’s not the feud that defines Leno’s legacy. In fact, he and Kimmel have since made peace. Leno even reached out to Kimmel during a personal crisis—when Kimmel’s son underwent heart surgery.
“I called him,” Leno said simply. It was a gesture that spoke louder than any punchline. And Kimmel has acknowledged the moment, saying he “made peace” with Leno because of it.
It’s a reminder that even when careers collide in smoke-filled NBC studios, time has a way of softening the edges.
More Than Late-Night Drama: Leno’s Career Is About Resilience
What separates Jay Leno from many of his late-night contemporaries isn’t just how long he worked—it’s how he handled the fallout. The brothel story, the Kimmel humiliation, the Conan-era chaos—they’re all part of a larger narrative about sticking it out and not always playing the ego game.
Leno didn’t just survive television’s most unpredictable decade; he did it with a sense of realism that few talk-show hosts have ever shown. He messed up, he trusted the wrong people, and he took the heat. But he never let it break him.
Jay Leno’s Legacy Isn’t Just About Comedy—It’s About Showing Up
In an era when late-night hosts are often defined by how sharply they can attack one another, Leno’s story stands apart. He’s not advertising a comeback or digging up old grudges. He’s simply reflecting on what happened—and doing it without needing to rewrite the past.
Fans of superhero universes and comic book sagas know the value of an honest origin story. Jay Leno’s might not involve gamma rays or enchanted hammers, but it’s just as real. And that’s probably why it matters more than most.