Jay Leno Spills on Potential David Letterman Reunion: “Might Be Awkward!”

Over three decades after their famed rivalry, Jay Leno is now expressing openness to a reunion with David Letterman, suggesting he’d participate if the opportunity arose.

The veteran late-night TV host recently shared that he’d be willing to collaborate with Letterman again, though he’s hesitant to initiate anything given their historically “awkward” interactions.

“Absolutely, I’d be up for it. I don’t foresee any issues on my end,” Leno remarked during an interview on In Depth with Graham Bensinger. “It might be a bit awkward for Dave, though.”

Leno described Letterman as “a bit eccentric,” quickly noting that he meant no offense by it. He admitted he’s somewhat eccentric himself, just in a completely different way.

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Leno recounted a time he and comedian Wil Shriner unexpectedly dropped by Letterman’s house in Malibu while out riding motorcycles. “We thought, ‘Let’s just pop in.’ It turned out to be incredibly awkward. Dave was like, ‘Uh, hi? Oh, sure, come in.’ And we immediately knew it was a mistake,” he explained.

“The whole visit was just uncomfortable,” Leno continued. “‘So, do you want some orange juice?’ ‘No, we’re good. Actually, we should get going.’ It felt forced because outside of comedy, we don’t share many interests. Dave loves sports; I don’t follow them much… But hey, if there’s a chance to reunite for a project, I’m in. Although, past experiences have taught me to be cautious about initiating such things.”

Leno’s career was notably intertwined with Letterman’s when he appeared on Late Night with David Letterman, before controversially being selected over Letterman as Johnny Carson’s successor on The Tonight Show in 1992. This decision was famously dramatized in the HBO movie The Late Shift in 1996.