Jay Leno Recalls Dorchester Brothel Gig And Kimmel Feud
In a candid interview, comedian Jay Leno reflected on his early career performing in unusual venues, including an unexpected gig at a brothel operating out of a Dorchester triple-decker, as well as the infamous 2010 feud with Jimmy Kimmel that continues to resonate today.
The former “Tonight Show” host shared these stories during a wide-ranging conversation that touched on his formative years in Massachusetts and pivotal moments in his late-night television career.
Unexpected Early Career Venue in Boston
Among the most surprising revelations was Leno’s recollection of performing at what turned out to be a brothel operating out of a three-decker house in Dorchester. “That was a guy in Dorchester, it was a three-decker house,” Leno explained, noting that he only realized the true nature of the establishment after arriving, according to The Boston Globe.
Leno described walking into a room filled with men carrying lunch pails and sporting three-day beards, who were clearly not there primarily for comedy entertainment. The comedian quickly realized the unorthodox nature of the venue when he understood that “the girls were on the second and third floor” of the building.
“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,” Leno recalled of the unexpected audience at the establishment.
Addressing the Kimmel Confrontation
In a more introspective portion of the interview, Leno revisited his infamous 2010 interaction with Jimmy Kimmel, which occurred during the contentious period when Leno returned to host “The Tonight Show” after Conan O’Brien’s brief tenure.
Kimmel appeared as a guest on Leno’s show and proceeded to criticize him directly on air for his handling of the O’Brien situation. When asked about the best prank he’d ever pulled, Kimmel responded with a pointed jab: “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,” as reported by Variety.
Reflecting on the incident, Leno acknowledged: “When Kimmel came on my show and humiliated me on my own show, I let it happen. I didn’t edit it. It was my mistake, I trusted somebody.”
Taking Responsibility for the Aftermath
Rather than expressing bitterness about the confrontation, Leno showed a sense of accountability for the situation and its consequences. When asked why he didn’t edit out Kimmel’s critical comments before the episode aired, Leno responded with a straightforward explanation.
“Because it happened,” Leno stated. “It’s real — it happened. It’s my mistake. That’s how you learn.” He noted that while some might view the dramatic moment as “good TV,” he sees it differently, adding, “It’s not good TV for me because it started a whole thing that continues to this day, really.”
The late-night host’s willingness to accept blame for the awkward exchange shows his perspective on handling public missteps and career controversies.
Relationship Evolution and Current Standing
Despite the long-running tension between the two comedians, their relationship has reportedly improved in recent years. According to multiple sources, the ice began to thaw in 2017 when Leno reached out to Kimmel after the latter’s son underwent heart surgery.
Kimmel has publicly acknowledged this gesture, stating he “made peace” with Leno following the kind outreach during a difficult personal time. Nevertheless, the relationship between the two remains complicated, with Kimmel occasionally making references to their past feud.
As recently as March 2025, following Conan O’Brien’s successful hosting of the Oscars, Kimmel joked that he had heard the Academy was planning to give the hosting job to Leno next year — a clear reference to the circumstances that sparked their original confrontation.
