Mostly interview shows. Mostly entertainment-centric.
  1. WTF with Marc Maron
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    This is the godfather of all interview podcasts, the Velvet Underground of the medium. For my money, it's also the best. Maron is Howard Stern, Dick Cavett, and my narcissistic father all rolled into one. The episodes with personal connections are probably the most compelling, but as the show has gotten bigger it has become a veritable archive of definitive interviews with everyone in the arts that you could possibly want to hear talk for an hour and change.
  2. The Moment with Brian Koppelman
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    Interviews that focus on the highs and lows of successful people's lives and how they processed them. Koppelman is a filmmaker who's very smart, kind, & open hearted. If Maron's your asshole dad, Koppelman's your compassionate mother. His talks with everyone from Seth Meyers to Baron Davis to Amy Schumer (and on and on) are fascinating for their insight into what it takes to live a life making things. Always surprised by the ones where I'd never heard of the guest. He has them on for a reason.
  3. Gilbert Gottfried's Amazing Colossal Podcast
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    A qualified recommendation. Really only for deep show business needs like myself. It almost sounds like a joke that someone whose voice sounds like Gottfried's would have an interview show, but it's worth listening to be able to hear people like Mike Reiss, Alan Zweibel, Henry Winkler, and Barbara Feldon talk at length. If you only listen to one, make sure it's the Danny Aiello episode, as candid as anything I've ever heard: "Fuck Mahtin Scohsese! That midget never put me in any of his movies!"
  4. The Bret Easton Ellis Podcast
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    Basically just BEE asking different people (Kanye, Judd Apatow, etc.) what they thought of "12 Years a Slave." Joking aside, it's an interview show with more of a pop culture bent and less of a biographical or emotional one. Slight but listenable.
  5. BAFTA Screenwriters Lecture Series
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    Invaluable for writers of any kind or anyone curious about writing. Particularly Tony Gilroy and Scott Frank's lectures. So much better than any screenwriting book is being able to hear real writers talk about how they do it.
  6. Here's the Thing with Alec Baldwin
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    Updated in fits and starts and occasionally very good and engaging. Great if only to hear what it would be like for the Royal Tenenbaums narrator to interview people like David Simon, John McEnroe, David Letterman, Jerry Seinfeld, Chris Rock, Julianne Moore, and sick fuck pervert Jim Toback.
  7. By the Way, In Conversation with Jeff Garlin
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    Never emotional but always fun. Great guests with occasional awkward-Largo-audience member interactions. Garlin has quite a laugh, though, which I'd never noticed before listening to this.
  8. The BS Report with Bill Simmons
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    Padded out with a lot of episodes I don't listen to, but worth wading through for unbelievable conversations with people like Lorne Michaels, Larry David, Louis CK, Lena Dunham, and Seth Meyers.
  9. You Must Remember This
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    Excellently produced with lots of awesome old Hollywood stories. Another one that probably won't appeal to people who aren't insane movie nerds.
  10. The Talkhouse
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    Filmmakers talking to filmmakers. Too short and sort of hit and miss but worth investigating for the Rian Johnson/Terry Gilliam conversation among others.
  11. Fresh Air with Terry Gross
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    Kind of a cheat, since it's really on NPR, but this has been a great institution for intelligent conversation for years. Gross is sometimes a little too sort of politically correct or liberal-guilt-proper for me, but the show is often smart and incisive.
  12. Scriptnotes with John August & Craig Mazin
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    Another good screenwriting podcast. These guys break everything down in a way that is incredibly digestible and inspiring.
  13. The Treatment with Elvis Mitchell
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    Solid interview series that's a little more junket-y (which is antithetical to what I love about the podcast format) but still makes for some interesting conversations. Even if you just want to hear how some pretentious dickhead defends their shitty movie.
  14. Serial
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    It's almost pointless to put this on the list, since anyone that has heard of podcasts has almost certainly heard of Serial. But it's easy to forget how good things are when they become obscured by the cloud of overexposure, the way you can take The Beatles for granted until you put on Revolver and are reminded of why they're as popular as they are. Serial isn't The Beatles but it's fucking excellent.
  15. The Best Show
    Suggested by @johannasamuels