In a comedy and entertainment universe that’s changing with increasing velocity, the task of being interesting, and staying interesting, is a crucial and immensely difficult one. But that’s the operating reality of the business, even if your repertoire includes a masturbating bear.
Conan O’Brien is the longest-serving late-night talk-show host in the business, and he also happens to be one of the more interesting players of the mainstream comedy game. His consistent interestingness isn’t just limited to his actual material — often typified by an immense weirdness — but also extends to what’s clearly a deft understanding of the structures around him. O’Brien, after all, is the kind of entertainer that’s equally responsible for things like “Clueless Gamer,” which is as much a triumph of native advertising as it is a comedic commodity; Conan Without Borders, a series of travel specials (now streamable on Netflix) best described as a bizarro version of the late Anthony Bourdain’s work, in turns absurd and heartfelt; and even a genuine documentary, as in the case of 2010’s Conan O’Brien Can’t Stop, which followed the comedian as he mounted a string of live shows around the country in the aftermath of the Tonight Show debacle that temporarily prohibited him from performing on television.
One could argue that O’Brien is a particularly willing crucible for all the change that’s constantly disrupting the comedy world: digital media, distributed audiences, democratized competition. And that logic only appears to be intensifying as he gets deeper into fourth decade of his career. Later this month, O’Brien will debut a slimmed-down version of his TBS show, Conan, which will scale down some of the more conventional talk-show aspects and introduce newer, radically different things into the mix. The move is being billed as a natural extension of his efforts to become more modern and digital-friendly as a comedy brand.
It makes sense, then, that a podcast would be part of that effort. After all, the podcast scene is bumpin’, and basically everybody has a podcast these days, from various news organizations to government agencies to various talented aspirants to professional athletes to your cousins and aunts. Also, and more importantly, podcasting as a business proposition naturally fits into O’Brien’s strategy: Podcasting proponents champion the medium’s intimacy and its particularly strong capacity to facilitate direct relationships between the comedian and his fans.
Conan O’Brien Needs a Friend, the comedian’s new weekly interview podcast, debuted last November with a killer lineup of initial guests. The show kicked off with Will Ferrell, and in the eight weeks since it debuted, the show has followed up with celebrities like Kristen Bell, Wanda Sykes, Nick Offerman, and Megan Mullally, but also celebrity podcast veterans like Dax Shepard, Bill Burr, and Pete Holmes. This week saw the release of the podcast’s eighth episode, its best so far, which featured a rollicking, fascinating interview with the podcast stalwart Marc Maron that involves a sharp detour into the whole Tonight Show affair. (“When you hosted The Tonight Show, why didn’t you have me on?” Maron asked, in classic form. “Because it only lasted for 45 minutes?” O’Brien replies.)
As a production, Conan O’Brien Needs a Friend is a really savvy piece of business. To build the show, Team Coco, O’Brien’s production company, partnered with Earwolf, the heavyweight comedy podcast network that’s home to, among other things, Scott Aukerman’s Comedy Bang! Bang! and the widely loved paean to bad movies, How Did This Get Made? (A mildly interesting connection to note here: Team Coco’s current chief operating officer, Adam Sachs, who is also an executive producer on the podcast, was the former head honcho of Midroll Media, Earwolf’s parent company.) Matt Gourley, a podcast legend in some circles (see: Superego), serves as the show’s producer and a secondary sidekick. Gourley brings with him considerable expertise in assembling a project like this, and the end result is a really slick product. Remember: For a production like this, if it sounds casual, that’s because someone meant it to sound that way, and a lot of work goes into creating that aesthetic.
There is, ostensibly, a conceptual hook to the podcast: O’Brien, noted self-deprecator, is worried he has no real friends beyond the staffers on his payroll, and therefore embarks on a quest to find out if he can actually be friends with any of his famous guests. It’s a good framework gag, but it ends up only being marginally utilized, for better or worse. For the most part, Conan O’Brien Needs a Friend is a fairly conventional comedy-interview show, which is to say, expect mostly straightforward if not casual interviews punctuated by bits and surreal digressions depending on the guest. Each interview is also generally followed by an extra segment that involves some banter work between O’Brien, Gourley, and Sona Movsesian, his personal assistant and podcast foil/sidekick.
So, eight episodes might be a small sample size — Earwolf is apparently getting at least 36 weeks — but still, it’s enough to say: All of it really works. You’re probably already in the bag for this project if you’re a Conan O’Brien fan, but for a comedy civilian like myself, there’s a lot of meat to pick on this bone. O’Brien is a really good fit for the medium, as it turns out. His weirdness translates well to the casual intimacy that’s come to define the podcast as a platform for performance, and his default stance of efficient self-deprecation makes the show feel accessible in ways that other comedy podcasts, fronted by needier ids, may not. It also helps that O’Brien is great at the performance of longer-form interviews, effectively balancing the impulse of filling the room with being genuinely curious, and there’s also a lot of charm to be found in the podcast, particularly in the core O’Brien-Movsesian-Gourley workplace dynamic, which goes a long way to providing listeners with a sheen of habitual comfort. (A representative gag: “I’m the only late-night show — maybe the only entertainer in America — who has gone to the home where Trotsky was murdered, and not only that, I went to the gift shop.” And so on, and so forth.)
I’m partial to thinking that the thing about the intimate, supposedly revealing longer-form interview show is that it’s really a story about the interviewer told in small increments, with guests being the catalyzing incidents that draw out the narrative. The most transparent version of this, perhaps, can be found with the aforementioned Marc Maron, who has historically used his iconic interview podcast, WTF With Marc Maron, as a site of both autobiography and therapy in addition to being a vessel for interviews. But I also like to think it’s equally applicable to something like Getting Curious With Jonathan Van Ness and Death, Sex, and Money. The habit-forming appeal is supposed to be in the host (i.e. the constant), and the end result is the continuous production of celebrity.
O’Brien’s entry into the celebrity interview podcast genre introduces a complicating factor to the theory: What happens when you run that story experience through a particularly visible celebrity whose story has been deeply, consistently, and loudly told? How big a celebrity can you be before the espoused intimacy of the medium simply doesn’t work for you? Given that we’re currently in the midst of some sort of renewed boom in celebrity podcasts — embodied by shows like Dax Shepard’s Armchair Expert and Anna Faris Is Unqualified (also, did you hear that even Dr. Phil has a podcast now?) — we’ll probably end up grappling with that line of inquiry a lot more. But for now, and for what it’s worth, those questions don’t really seem apply to O’Brien. Whether it’s the nature of his celebrity or his specific creative gifts, each episode continues to dole out really interesting increments of the comedian’s brain, personality, and story. The direct relationship with the longest-tenured late-night show host still works. And eight episodes in, that interestingness doesn’t seem to be drying up anytime soon.