Discover Jay Leno’s career regrets from 2010 and his reconciliation with Kimmel.
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What’s the real story behind Jay Leno’s biggest career regret?
It all started in 2010 when Jimmy Kimmel stepped onto Leno’s stage and didn’t hold back.
Kimmel called out Leno for breaking his promise to pass The Tonight Show to Conan O’Brien, a move that shook late-night TV.
Ratings tanked for Leno’s shows, and things got messy fast—O’Brien said no to a later slot, forcing Leno back into the spotlight.
Did Leno see that moment coming?
Not really, but he owned it. During his recent chat on In Depth With Graham Bensinger, Leno explained why he let Kimmel’s jabs air unedited.
He’d trusted the wrong people, he admitted, and figured it was his mess to clean up.
“It’s my mistake,” Leno said simply, adding that you learn from these hits.
Yet, even now, he doesn’t call it “good TV”—it sparked a feud that’s lingered for years.
How has this affected their relationship over time?
It’s been a rollercoaster, but they’ve moved on.
Back in 2017, after Kimmel’s son had heart surgery, Leno reached out with kind words, and they patched things up.
Kimmel even gave Leno props for his success and staying power in the industry.
While Leno wouldn’t have pulled the same prank, he gets that comedy’s a tough game—it’s what you do to survive.