Marc Maron’s recent announcement that he’s ending his long-running podcast may have come as a surprise, but it’s not like the guy hasn’t earned a break. The comic has delivered two episodes a week for 16 years, even as his workload has grown significantly with comedy specials and acting gigs in such series as GLOW and Stick and films like The Joker and Springsteen: Deliver Me From Nowhere. So as this moments finds many revisiting his legacy or discovering him for the first time, here are a few of the many must-listen conversations — both heartbreaking and hilarious — that he’s had since he helped pioneer the medium. (For more on Maron, read The Hollywood Reporter’s cover story.)
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Episode 67
Robin Williams
Later inducted into the National Recording Registry at the Library of Congress, the episode features the late comic on insecurities and suicide.
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Episode 147
Gallagher
When Maron questions the watermelon-smashing comic on his homophobic and racist remarks, we hear the first-ever WTF walk-off. “Come on, Gallagher!”
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Episode 613
President Barack Obama
The Secret Service came to Maron’s house for one of the essential texts in WTF history and of the Obama presidency.
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Episode 627
Image Credit: Suzi Pratt/Getty Images for SIFF Lynn Shelton
This blind date between eventual partners doubles as a lovely portrait of a filmmaker whose brilliant career was cut far too short.
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Episode 653
Lorne Michaels
Maron gets to air his grievances over his failed SNL interview for a particularly game Michaels, who so rarely (read: never) gives this much of his time.
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Episode 1026
Mavis Staples
The then-80-year-old R&B singer mines her colorful career in what’s regarded as one of WTF‘s best conversations.
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Episode 1086
Brad Pitt & Leonardo DiCaprio
Not one but two A-listers pay a visit to talk about the ’90s and mega-fame, all while fawning over the host.
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Episode 1271
Jane Goodall
Another example of Maron’s diverse interests, the acclaimed primatologist low-key suggests that Bigfoot is real before this recording stops.
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Episode 1359
Andrew Garfield
The Garfieldnaissance can be traced to this winning hour where the actor opens up about career anxieties and losing his mother.
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Episode 1616
Ariana Grande
A pop star at the top of her game, Grande gets real and tries to get even realer: “I thought we’d be talking a lot more about death.”
This story appeared in the Aug. 13 issue of The Hollywood Reporter magazine. Click here to subscribe.