Jay Leno: Why David Letterman Reunion Would Be ‘Awkward’ (But I Want It Anyway!)

People who know Jay Leno from his recent appearance on Shifting Gears, or David Letterman for that matter, are likely aware of the tension that developed between these two talk show hosts in the early 1990s following Johnny Carson’s retirement from NBC’s The Tonight Show. Initially, Leno was chosen to replace Carson, even though Letterman had been hosting Late Night on the preceding time slot and many believed he was Carson’s intended successor. Since then, Leno and Letterman have not maintained a close relationship, but Leno recently expressed his thoughts about a potential reunion with Letterman, stating it would be “awkward.” However, this comment has sparked my hope that such an encounter might actually take place in the near future.

During a comprehensive chat on “In Depth with Graham Bensinger”, the show’s host casually mentioned he had been talking to the executive producer of “Jay Leno’s Garage”. This individual expressed that there would be nothing more fulfilling in life for him than seeing Jay Leno and Letterman together again. Here’s what Jay Leno responded:

*Jay Leno replied:*

“I must admit, I share the same sentiment. The thought of reunion with Dave brings me immense joy as well.

Absolutely! I’m game for that endeavor. From what I can tell, it seems quite feasible for me. As for Dave, he’s an eccentric individual, not in a negative sense, just uniquely his own.

Before the events surrounding The Tonight Show, Jay Leno and David Letterman were acquainted, as Leno often appeared on Late Night with David Letterman. Simultaneously, Leno began standing in for Johnny Carson on The Tonight Show from 1986. NBC seemed to believe that Leno was the ideal choice to take over from Carson following this decision, despite the ensuing uproar. However, Leno reminisced about an uncomfortable interaction with Letterman; he recounted one such instance: “I remember an awkward run-in with Letterman.

One time, Will Shriner, another comedian, and I were on our motorcycles. We suggested impulsively to pay a surprise visit to Letterman at his home in Malibu. The day turned out to be incredibly awkward. Dave looked puzzled, muttered ‘Huh?’, then stammered ‘Yeah… come on in.’ We felt it was a mistake. He asked if we’d like some orange juice, but we politely declined and left quickly. It was an awkward encounter because our shared interest was limited to comedy, as Dave is more into sports, and I’m not.

Indeed, that situation embodies almost perfectly the classic understanding of awkwardness, and adding their contrasting opinions certainly doesn’t bolster the case for rekindling their relationship. However, this doesn’t mean Jay Leno would turn down the chance if it were offered; instead, he’s not likely to actively pursue it. As he himself expressed:

To clarify, if they wish to act upon something, I’d be willing to join in. However, I prefer to avoid situations where I might end up regretting my actions, as I’ve learned that getting involved in such matters can lead to unwanted consequences.

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I’m not asking them to be best friends, but it would be great if Jay Leno and David Letterman could do a TV special together. It’s been more than 30 years since their feud over “The Tonight Show,” as detailed in Bill Carter’s book “The Late Shift” and later adapted into a TV movie available with a Max subscription. I believe enough time has passed that, given the right circumstances, they could have an insightful and engaging conversation for us to watch.

Check out the latest episodes of Jay Leno’s Garage on YouTube, while David Letterman’s current show, My Next Guest Needs No Introduction, can be enjoyed with a Netflix subscription. By any chance, if Jay Leno and David Letterman were to appear together again, it could potentially bring Jay Leno and Conan O’Brien into the same room… or is that wishful thinking?

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2025-04-25 03:08