Jay Leno Recalls ‘Awkward’ Encounter With David Letterman

David Letterman may be a legendary TV host, but according to Jay Leno, the “quirky” host was less than welcoming when Leno once popped in at his house unannounced.

Guesting on In Depth with Graham Bensinger, Leno recalled a long-ago memory of riding motorcycles with comic Will Shriner when the two decided to drop by Letterman’s house for a friendly pop-in.

“Hey, let’s stop in Malibu and see Letterman,” Leno recalled thinking. “Let’s just surprise him at his house.”

Letterman, however, was thrown by the visit. “It was the most awkward—“ Leno began. “Dave was like, ‘Huh? Oh, uh, yeah. Come on in.’”

“We’re like, ‘Oh, this was a mistake.’” Leno added. “It was just so awkward… Because you have nothing else in common other than comedy, really.”

During the interview, Bensinger noted that Leno’s executive producer had told him “it would bring him no greater joy in life than to see the [Leno and Letterman] reunited.”

“What do you think has to happen?” Bensinger asked Leno.

“I have no idea,” Leno answered. “Dave’s a quirky guy. I don’t mean that in a bad way.” Asked if he is ‘quirky’ too, Leno said, “I guess so, but opposite sides of the coin.” 

Even so, Leno says he’s open to rekindling their relationship. “Believe me, if Dave wanted to do something, I would do it,” Leno added. “But I tend to get my hand bitten when I instigate these kind of things.”

As proof, Leno went on to recount when an incident surrounding Letterman’s 2000 heart surgery. Letterman’s team, he said, had asked him not to mention anything about it on air. Within weeks, Leno was being slammed in the press for being the only late-night host to not offer Letterman well-wishes.

But Leno doesn’t seem to hold that incident against Letterman personally. “I don’t mistrust Dave. I like Dave,” Leno told Bensinger. “I think he’s great. He still makes me laugh more than anybody else.”

Leno also offered up another late-night host as an example of getting his hand bitten: Jimmy Kimmel. “When Kimmel came on my show and humiliated me on my own show… It was my mistake. I trusted somebody,” Leno said. “I should pay the price.”

Coincidentally, Kimmel recounted an awkward encounter with Leno of his own during his interview with Ben Affleck last night, detailing how the run-in went down at Affleck’s Christmas party.

“I came to your house for Christmas. I walk in the door, and then Jay Leno walks right in after me,” Kimmel told Affleck. “And we’re both uncomfortably making small talk with you, and you go, ‘Oh yeah, you guys have some thing with each other right?’ And I had to stand there… You just dropped a grenade right on us and went through.”

“Have you guys been insulting each other publicly for decades?” Affleck, who was unaware of Kimmel and Leno’s feud, recalled thinking. (Kimmel didn’t specify when the awkward Christmas party encounter occurred.)

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