What did David Letterman say about Jay Leno? Feud timeline explored as former Tonight Show host says reunion might be awkward

Jay Leno is not keen on a reunion with David Letterman over 30 years since they first began feuding.

According to a Deadline report:

The late night host recently said if a reunion was in the cards, he “would do it,” but he doesn’t want to “instigate those kind of things” after having his own “awkward” encounters with Letterman.

The report added:

“Oh, yeah. I would like to do that. I think I have no problem with it,” Leno said on In Depth with Graham Bensinger. “I think Dave might be awkward.”

Jay Leno, called Letterman,

“a quirky guy,” explained that he doesn’t “mean that in a bad way.” He noted that he’s also quirky, “but opposite sides of the coin.”

The pair have long been at odds, though Letterman was the first to take shots at Leno. According to The Wrap, back in 2013, he told Oprah Winfrey:

Jay Leno is “the funniest guy I’ve ever known” — but also “maybe the most insecure person I have ever known.”

Scroll down to know all about their feud.

The decades-long feud between David letterman and Jay Leno, explored

Jay Leno and David Letterman's feud dates back to 1992, when Johnny Carson stepped down from his role as host of The Tonight Show. At the time, several late-night viewers presumed the title would go to his protege, David Letterman, then 45 years old. However, Jay Leno would assume the role, kicking off a hosting stint that would span 17 years — and an equally long feud with Letterman.

Shortly after, Letterman sat down as a guest on Tonight, when Carson asked him:

“Just how p—ed off are you?”

Letterman replied, jokingly suggesting that if he continued with language like that, he was going to find himself without a job.

By 1992, Letterman dropped his NBC show Late Night with David Letterman to launch Late Show with David Letterman on CBS, placing him in direct competition with Leno.

In 2010, the pair set aside their differences momentarily to shoot a Super Bowl commercial, though at the time, Letterman took shots at Leno by imitating him. By 2013, shortly after it was announced that Jay Leno would be retiring from Tonight, Letterman took shots once again, noting that his competition was “going out on top."

He also poked fun at the futile attempt a few years earlier of trying to replace Leno with Conan O'Brien.

“It seems like we just went through this. Didn’t we just go through this? Jay Leno now is being replaced, and this is the second time this has happened,” Letterman joked. “I mean, it’s crazy. He’s being replaced by a younger late-night talk show host–what could possibly go wrong?”

In January 2023, Jay Leno sat down with Chappelle’s Show co-creator Neal Brennan, where he said, that at the time, the time slot belonged to NBC and David Letterman was not on good terms with a lot of people, suggesting that all he did to kick start the feud between the two was accept a coveted job.

“You know, I love Letterman,” Jay Leno told Brennan. “The thing I liked about it was that I got the ratings and Dave got the critics, and that seems fair. And you know something, if you flipped it, that would be okay, too. I think we both did okay in that way.”

However, Leno also said that it was a feud built on a foundation of mutual respect.

“He and I were the perfect foil for each other. Because, any time I spent with Letterman, I always left with more material than I came in with. We would have a conversation and we’d both be laughing, and there’s no greater joy than putting something in that Letterman genuinely laughed at,” Leno recalled of when they would do stand-up on the same circuit. “Because Letterman didn’t always find things funny.”

For Jay Leno, Letterman is still as funny as he was:

“To this day, Letterman makes me laugh as much as anybody. Fascinating character, funny, and there’s a connection we have that I can’t describe,” Leno said. “It’s like s*x: I don’t care how it works. It works. Just leave it. I like to make love, I don’t wanna be a gynecologist.”

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Leno served as a recurring guest star on Letterman's original NBC Late Night series through the 1980s before their bond turned sour. Their feud would eventually go on to serve as the inspiration for the bestselling book and HBO movie, The Late Shift.

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