Jay Leno revisits career lows: Fleeing brothel in Dorchester and ‘Tonight Show’ humiliation

The comedian's appearance at a three-decker house in Dorchester didn't last long.

Emily Sweeney | May 9th, 2025, 12:44 PM

Jay Leno recalled some less-than-proud moments in his comedy career during a recent appearance on “In Depth With Graham Bensinger.”

In a wide-ranging interview, Leno reflected on his formative years in Andover, how he was “humiliated” on “The Tonight Show” back in 2010, and the odd places he’s performed over the years, which included gigs at prisons, psych wards, and a brothel in Dorchester.

The gig in Dorchester took place in a three-decker house, which turned out to be a brothel.

“That was a guy in Dorchester, it was a three-decker house,” said Leno. “I guess the girls were on the second and third floor. So I walk in, I sit down, and it’s all men with lunch pails, you know, three-day growth,” Leno said, rubbing his chin.

“These guys are on their way home, their wife doesn’t know they’re there, you know, they got their lunch pail. They’re just trying to get in and out real quick, you know?”

Leno chuckled as he recounted how he was received there.

“So the guy thought this would be wonderful entertainment for these guys,” he said, laughing. “Hey, we got a comedian!”

“I start, [and] a guy goes: ‘Hey get out of here!’”

Leno took that as his signal to leave.

“I just ran away,” said Leno. “I just ran away.”

Leno also brought up another memorable moment from his career that happened in 2010, when he came back to host “Tonight Show” after Conan O’Brien left, and Jimmy Kimmel appeared on the show and poked fun at Leno.

“When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it,” said Leno. “It was my mistake, I trusted somebody. I went, ‘Ah, I made a mistake. Okay, I should pay the price.’ And it’s fine, it’s fine. I mean, we could have edited it out of the show.”

Bensinger asked: “Why didn’t you?”

“Well, because it happened,” said Leno. “It’s real, it happened. It’s my mistake. That’s how you learn, you know?”

“Did you view it as a mistake or is that good TV?” Bensinger asked.

“Well, it’s not good TV for me, because it just started a whole thing that continues to this day, really,” said Leno. “But it’s okay, it’s all right. He’s a comic — you do what you got to do. I mean, I wouldn’t have done it, but that’s okay. That’s all right. That’s okay. It is what it is.”

Comment count: