Anyone who’s familiar with Jay Leno (who recently cameoed on Shifting Gears) and David Letterman is almost certainly aware of the drama that unfolded between the talk show hosts in the early 1990s. After Johnny Carson retired from NBC’s The Tonight Show, Leno was tapped as his replacement despite the fact that Letterman had been hosting Late Night in the following time slot, and Carson had thought he was his natural successor. In the decades since, Leno and Letterman haven’t exactly been chummy, and though the former recently shared why he thinks a reunion with the latter would be “awkward,” it’s actually making me hopeful that it will actually happen.
During an extensive interview on In Depth with Graham Bensinger, the title host mentioned that’d been speaking with the executive producer for Jay Leno’s Garage, who said it would “bring him no greater joy in life” then to see Leno and Letterman reunited. Here’s what Leno had to say to that:
Oh yeah. I would like to do that. I think I have no problem with it. I think Dave might be awkward… Dave’s a quirky guy. I don’t mean that in a bad way.
Jay Leno and David Letterman were already well acquainted before this Tonight Show saga unfolded, as Leno had appeared numerous times on Late Night with David Letterman. At the same time, Leno started substitute hosting for Johnny Carson on The Tonight Show starting in 1986, and evidently NBC felt Leno was the better fit to succeed Carson. But even looking the turmoil that this decision spawned, Leno went on to share how he’s already had an awkward encounter with Letterman: He recalled:
I remember once Will Shriner, another comedian, we’re riding our motorcycles. ‘Hey, let’s stop in Malibu and see Letterman. Let’s just surprise him at his house. It was the most awkward day. Dave’s like, ‘Huh? Oh, uh, yeah. Uh, come on in.’ And we’re like, ‘Oh, this is a mistake,’ It was just so awkward. ‘So, uh, you want a glass of orange juice?’ ‘No, I’m ok. Yeah. We gotta get going.’ It was just so awkward… because really, you have nothing else in common other than comedy really. Dave’s a sports guy. I’m not a sports guy…
Yeah, that’s practically the textbook definition of awkward, and when you throw in their differing views, that doesn’t make the strongest argument for pairing them back up. That’s not to say Jay Leno would refuse the opportunity if it came along, but he’s also won’t go out of his way to make it happen. As he put it:
But I mean, believe me, if they want to do something, I would do it. But I’m not gonna… I tend to get my hand bitten when I instigate those kind of things.
Look, I’m not saying we need to see them acting like the best of friends, but I would sincerely like it if Jay Leno and David Letterman sat down together for some kind of TV special. It’s been over 30 years since the conflict between these two concerning The Tonight Show, which was covered in the Bill Carter-penned book The Late Shift, and that in turn was adapted into a TV movie that can be viewed with a Max subscription. I’d like to think enough time has passed that in the right environment, they could have a thoughtful and compelling discussion for others to enjoy.
New episodes of Jay Leno’s Garage can be found on YouTube, while David Letterman’s current talk show, My Next Guest Needs No Introduction, can be streamed with a Netflix subscription. And hey, if by some chance Leno and Letterman do reunite onscreen, maybe that can help with getting Leno and Conan O’Brien in a room together… or is that asking too much?
