Conan O’Brien’s Podcast With David Letterman Was Utterly Fascinating

It was maybe halfway through David Letterman’s podcast appearance on the Conan O’Brien Needs a Friend podcast where the two former hosts of Late Night started discussing Bob Hope and Bing Crosby’s On the Road movies – and this is the point where Letterman pauses the conversation to explain to Conan there’s nobody listening anymore. (For the record, I was enthralled.)

And, yes, for anyone who might want to just listen to these two complain about Jay Leno, there might have been some disappointment. It’s true, these are the only two people on Earth who know what it’s like to lose a dream job to Jay Leno, but over the hour-plus conversation, Jay Leno’s name is mentioned a grand total of one time. And even then Leno’s name is tossed off in passing by Letterman of an example of things he doesn’t really enjoy talking about. So, no, this didn’t wind up being the epic, once and for all, comparison of “losing the The Tonight Show,” but it became something much more interesting.

— Conan O'Brien (@ConanOBrien) October 7, 2019

It’s weird that after all these years Conan and Dave have never been part of longer-form sit-down of any kind. Sure, yes, the two have yukked it up on their respective late-night shows, but there’s only so much depth that can come from those shorter interview formats. Look, I’ve always enjoyed Conan’s interview style – and the new format of his late-night show let’s that come out even more – but it’s on his podcast where his deft skills as an interviewer really come out. And Conan’s skill as an interviewer comes from three things: (1) He’s actually listening to what his guest is saying, (2) he then engages with what the guest has said, and (3) Conan obviously possesses the wit and personality to make that engagement interesting.

There’s a great example of just this during his Letterman interview. Conan had asked a few questions about Dave’s Late Night, then mentioned to Letterman that he had applied as a writer, but got turned down. After exchanging some pleasantries, Letterman says he doesn’t want to talk about his show anymore. Now, not in a mean way, but in a more, almost folksy, “Let’s stop talking about that and talk about this instead.” To Conan’s credit, he pivots with Dave and winds up getting a lot of the same answers out of him, only with a slightly different subject.

But as Letterman and Conan kept talking, there was an overarching theme of why the job of “late-night host” made the two of these people – mind you, two of the best people ever at this job – so unhappy. It’s fascinating to listen to, and nuanced enough in the way they explain themselves I wouldn’t want to try to add any context. But it was telling when the subject of Johnny Carson was brought up. Letterman reveres Carson in the same way that Conan reveres Letterman, but it was Conan who brings up an interview Carson did in 1980 – 12 years before Carson would retire – where he laments that all the greats (people like Jack Benny) are gone. And Conan’s initial response to this was, “You just had Burt Reynolds and Steve Martin on your show, what are you talking about” But then Conan said, later, it started to make sense, because in the first few years of hosting a show you’re sitting there with all your heroes. At the end, as Conan puts it, they’ve all been replaced and you have to find something interesting to talk about with a star of One Tree Hill.

Conan had another Carson story, his only interaction with him. Carson did a voice for The Simpsons (it’s weird to think The Simpsons has been on long enough that both Carson and Bob Hope once did cameos) and says, “Carson was in no hurry to leave.” Basically it had been a year since Carson had left The Tonight Show and hadn’t been around comedy writers in a while and was really seeming to enjoy himself. It’s actually a little heartbreaking. And Letterman has never really said this, but it seems somewhat obvious he’s taken lessons again from his old hero, Carson, but only this time it’s a lesson in what not to do. Between Letterman’s Netflix show, My Guest Needs No Introduction, appearing in the Between Two Ferns movie, and just seemingly being “around” for the occasional podcast (he also did Marc Maron’s show recently, which covered a lot of Letterman’s early days and is also fascinating), Letterman finally gets the best of both worlds. He gets to be around “the business” when he wants to be, but also gets to spend a lot of time with his family. He’s certainly not going the “recluse” route like Carson did.

But Conan, too, when you listen to him, he sounds like he’s at a crossroads. During this podcast, he did that half-jokingly, half not thing where he listens to the reasons Dave retired from a daily talk show and says he feels the same way. And here’s something pretty surprising: Letterman hosted a late-night show for 33 years. Conan O’Brien has already hosted a show for 26 years. So, yes, of course he’s feeling the same way. But he seems to find honest to goodness pleasure out of this podcast. (Conan is a natural conversationalist, but the TV format is less about conversations and more about being “on.”) Conan says he now has the same problem Letterman did at the end, when sometimes he can’t remember who was on his television show from earlier in the day, but later during this conversation he has no problem rattling off all the interesting podcast guests he’s had.

The David Letterman/Conan O’Brien podcast didn’t have the bombastic quotes one might expect considering their similar history, but it almost felt like a therapy session for two legends of late-night – especially for Conan.

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