SHOCKING TURN OF EVENTS: Jay Leno’s Regret Over Jimmy Kimmel’s On-Air Humiliation That Sparked a Feud That Changed Late-Night TV Forever

In a candid and emotional revelation, Jay Leno, one of the most iconic names in late-night television, admitted to a decision that forever altered his relationship with fellow comedian Jimmy Kimmel. On April 25, 2025, during an appearance on “In Depth with Graham Bensinger,” Leno opened up about the infamous 2010 incident when Kimmel took jabs at him on his own talk show. Leno, 64, confessed that he allowed Kimmel to roast him in a moment that would not only fuel a long-standing feud but also shape the dynamic between the two late-night legends.

The 2010 Showdown: The Start of a Legendary Feud

The drama started when Jimmy Kimmel appeared as a guest on “The Jay Leno Show” in 2010. What was supposed to be a lighthearted appearance quickly turned sour when Kimmel, known for his biting humor and irreverent style, began making public jabs about Leno’s handling of the “Tonight Show” debacle.

In 2009, Leno had stepped down from his position as host of “The Tonight Show” to make way for Conan O’Brien, but when ratings plummeted, Leno was brought back, pushing O’Brien out. The situation caused a significant public outcry and became a defining moment of Leno’s career. Kimmel, who had been a vocal supporter of O’Brien, seized the opportunity to mock Leno relentlessly, even referring to Leno’s actions as a “betrayal” of O’Brien and the late-night community.

The tension reached a boiling point when Kimmel, during his guest appearance, made a joke about Leno’s handling of the “Tonight Show” situation. “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,” Kimmel quipped.

Jay Leno’s Regret: Why He Didn’t Stop Kimmel

Though the audience laughed, Leno’s discomfort was palpable. But instead of cutting the segment short or defending himself, Leno allowed the conversation to continue, even as Kimmel’s jokes hit closer to home.

“I let it happen,” Leno admitted in his interview. “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.”

When Graham Bensinger asked Leno why he didn’t edit the exchange out of the show, Leno explained that he didn’t want to hide the moment. “It happened,” Leno said, reflecting on the incident. “It’s real—it happened. It’s my mistake. That’s how you learn.”

But Leno acknowledged that the decision to air the segment without editing it ultimately backfired. He confessed that while the exchange made for compelling television, it sparked a feud that continues to this day. “It’s not good TV for me,” Leno said. “It started a whole thing that continues to this day. But it’s okay, it’s alright.”

Kimmel’s Reaction: Moving Past the Tension

For Kimmel, the tension from the 2010 encounter seemed to simmer for years, with the two comedians taking occasional jabs at each other during their late-night monologues. Kimmel later revealed that their rivalry was rooted in his deep admiration for David Letterman, who had hoped to take over “The Tonight Show” after Johnny Carson’s departure. When Leno was chosen for the role instead, Kimmel’s loyalty to Letterman solidified his disdain for Leno.

However, in 2017, Kimmel admitted that the two had buried the hatchet. “We made peace,” Kimmel shared. “After my son had his operation, Jay called me and was very nice.” Kimmel’s son, William, had been born with a heart defect, and it was this personal crisis that led to a heartwarming reconciliation between the two late-night hosts.

The Birth of the Feud: A Battle of Late-Night Personalities

Despite their reconciliation, the origins of their feud remain a topic of discussion in late-night TV lore. For years, Kimmel had publicly mocked Leno for his role in the “Tonight Show” debacle, and Leno’s decision to let Kimmel’s jabs slide in 2010 only made matters worse. Leno admitted that the humiliation from that moment—especially from someone who had been a friend and colleague—left a lasting mark on him.

Looking back, Leno saw the feud as a consequence of their personalities—Kimmel’s brash humor clashed with Leno’s more restrained, “old-school” style. “He’s a comic,” Leno remarked about Kimmel. “You do what you gotta do.”

The Fallout: How It Impacted Both Hosts

While Kimmel has continued his late-night reign on “Jimmy Kimmel Live,” Leno’s career has taken a different turn. Leno retired from “The Tonight Show” for the final time in 2014 and briefly hosted a primetime show before taking a hiatus from the limelight. In recent years, he has focused on his passion for classic cars with “Jay Leno’s Garage.” Kimmel, on the other hand, has risen to become one of the most prominent late-night hosts in the industry, cementing his place with sharp political commentary and a more liberal stance.

Despite their rivalry, both men have acknowledged the impact they’ve had on each other’s careers. Kimmel once admitted that his “feud” with Leno helped push him into the public eye, while Leno’s decision to let Kimmel roast him in 2010 gave Kimmel the platform he needed to make a name for himself.

The Larger Picture: Personal and Professional Reconciliation

Ultimately, Leno’s regret over the 2010 incident serves as a reminder that even in a world of comedy and satire, there are real human consequences. Leno’s reflection on the encounter highlights the complex nature of their relationship—what was once a joke turned into a career-defining feud.

For Kimmel, the public spat was more than just a joke; it was a reflection of his loyalty to Letterman and his desire to challenge the establishment. The reconciliation, however, came at a time when both hosts were going through personal struggles—Kimmel’s son’s health battle and Leno’s own decision to step back from the public eye.

Conclusion: The Final Word

As Jay Leno and Jimmy Kimmel continue their late-night careers, their long-standing feud serves as a testament to the personal and professional challenges of being in the public eye. For Leno, the lesson learned from that infamous moment in 2010 has shaped his career and relationships in ways that are still unfolding today. For Kimmel, the encounter with Leno was part of a larger journey that led him to greater prominence and success.

Despite the bumps in the road, both hosts have proven that, in the world of late-night TV, personal growth, forgiveness, and humor can coexist—even when the stakes are as high as a national television audience.