Interview Podcasts12 picksUpdated June 2025

Podcast Interviews Worth Going Back To

The conversations that defined what a great podcast interview can be. Not just good episodes — the ones that changed the medium.

The best podcast interviews have something television interviews almost never do: time. The willingness to let a conversation develop, to follow a thread past where television would cut away, to sit with discomfort rather than pivot to the next question. The interviews here are worth studying for what they reveal about how the format works at its best.

What makes an interview memorable isn't the subject's fame or the host's name recognition. It's the quality of listening. The best interview hosts demonstrate that they actually heard what the previous answer was before asking the next question, which is rarer than it sounds.

For creators who do interview shows, studying these episodes is more valuable than studying interview technique in the abstract. Each one demonstrates a different approach to the same fundamental challenge: getting someone to say something they haven't said before.

How we chose these shows

  • The interview revealed something genuinely new about the subject
  • The host demonstrated real preparation rather than a list of prepared questions
  • The conversation developed naturally rather than following a scripted arc
  • The episode changed how listeners thought about the subject or the format itself
Joe Rogan with Elon Musk (Episode 1169)
#1
Technology and Culture

Joe Rogan with Elon Musk (Episode 1169)

Hosted by Joe Rogan Experience

Joe Rogan's 2018 interview with Elon Musk produced the most-watched podcast episode in history at the time, with the cigar and whiskey moment generating headlines globally and demonstrating that podcast interviews operate by different rules than conventional media appearances.

Why listen as a creator

The Rogan-Musk interview demonstrates what happens when a subject feels genuinely comfortable rather than managed. Musk said things in three hours with Rogan that he had never said and would never say in a conventional media interview, which is what the format is for.

Marc Maron with President Obama (WTF Episode 613)
#2
Political Culture

Marc Maron with President Obama (WTF Episode 613)

Hosted by WTF with Marc Maron

Marc Maron's 2015 interview with President Obama in Maron's garage produced a conversation about race, gun violence, and presidential power that the formal White House press environment had never generated, demonstrating what informal interview settings unlock.

Why listen as a creator

The Maron-Obama interview demonstrates that setting is part of interview technique. The garage, the informality, the host's willingness to be personally vulnerable alongside the subject produced a version of Barack Obama that was more candid than any formal presidential interview.

Ira Glass with David Sedaris (This American Life)
#3
Literary Interview

Ira Glass with David Sedaris (This American Life)

Hosted by This American Life

Ira Glass's years of conversations with David Sedaris on This American Life produced a body of radio interview work that defined what personal narrative interview sounds like when host and subject have complete trust in each other.

Why listen as a creator

The Glass-Sedaris body of work demonstrates what long-term interviewer-subject relationships produce. The conversations evolved over years as both host and subject changed, which made the accumulated record something neither a single interview nor a book profile could be.

Terry Gross with Gene Simmons (Fresh Air)
#4
Music Interview

Terry Gross with Gene Simmons (Fresh Air)

Hosted by Fresh Air

Terry Gross's 2002 interview with Gene Simmons produced one of the most famous interview confrontations in radio history, with Simmons' provocations and Gross's direct, unflappable responses demonstrating interview control under pressure.

Why listen as a creator

The Gross-Simmons interview demonstrates that interview control doesn't require matching a difficult subject's energy. Gross's steady, direct engagement with Simmons' attempts to derail the conversation is a masterclass in holding format under provocation.

Howard Stern with Lady Gaga (SiriusXM)
#5
Celebrity Interview

Howard Stern with Lady Gaga (SiriusXM)

Hosted by The Howard Stern Show

Howard Stern's interview with Lady Gaga is regularly cited as one of the most revealing celebrity interviews ever conducted, with Gaga discussing her childhood trauma, insecurities, and artistic process with a depth that no conventional celebrity interview had produced.

Why listen as a creator

The Stern-Gaga interview demonstrates what consistent vulnerability from the host unlocks in the subject. Stern's willingness to share his own therapy experiences and insecurities created the emotional safety that allowed Gaga to discuss things she had never publicly discussed.

Tim Ferriss with Arnold Schwarzenegger (Episode 60)
#6
Business and Achievement

Tim Ferriss with Arnold Schwarzenegger (Episode 60)

Hosted by The Tim Ferriss Show

Tim Ferriss's interview with Arnold Schwarzenegger is considered one of the best achievement interviews in podcasting, with Schwarzenegger discussing his systematic approach to success across bodybuilding, film, and politics in a way no biography had fully captured.

Why listen as a creator

The Ferriss-Schwarzenegger interview demonstrates that the best achievement interviews are about systems, not stories. Ferriss's question design produced a conversation about how Schwarzenegger actually approached each phase of his career rather than the mythologized narrative he'd told a hundred times.

Conan O'Brien with Jordan Schlansky (Conan O'Brien Needs a Friend)
#7
Comedy Interview

Conan O'Brien with Jordan Schlansky (Conan O'Brien Needs a Friend)

Hosted by Conan O'Brien Needs a Friend

Conan O'Brien's recurring podcast conversations with his producer Jordan Schlansky are the model for comedic interview as character study: the interview is both funny and genuinely revealing about two distinct personalities in extended, unfiltered collision.

Why listen as a creator

The Conan-Schlansky conversations demonstrate that comedy in interviews is most effective when the humor emerges from genuine personality clash rather than performance. Neither Conan nor Jordan is performing for the other; the comedy comes from their real inability to understand each other.

Lex Fridman with Vladimir Putin
#8
Political Interview

Lex Fridman with Vladimir Putin

Hosted by Lex Fridman Podcast

Lex Fridman's 2024 interview with Vladimir Putin was the first Western media interview with Putin in years, conducted entirely in Russian with translation, demonstrating what access journalism looks like when a podcaster can secure subjects that establishment media cannot.

Why listen as a creator

The Fridman-Putin interview demonstrates that access itself is news in interview journalism. Regardless of how you evaluate Putin's answers, the fact that a podcaster secured the interview that traditional media outlets couldn't is a statement about what the format has become.

Sam Harris with Yuval Noah Harari (Making Sense)
#9
Intellectual Interview

Sam Harris with Yuval Noah Harari (Making Sense)

Hosted by Making Sense with Sam Harris

Sam Harris's extended conversations with Yuval Noah Harari on artificial intelligence, consciousness, and the future of humanity produced some of the most substantive public intellectual dialogue in podcast history.

Why listen as a creator

The Harris-Harari conversations demonstrate what happens when two people are equally prepared and equally willing to push back on each other's positions. The disagreements between them are as illuminating as the agreements, which is the mark of an interview conducted without deference.

Brené Brown with Oprah Winfrey (Unlocking Us)
#10
Personal Growth Interview

Brené Brown with Oprah Winfrey (Unlocking Us)

Hosted by Unlocking Us

Brené Brown's interview with Oprah Winfrey demonstrated what happens when the researcher behind ideas that Oprah had popularized sits across from Oprah and discusses what the research actually says, rather than what the popular version of the ideas had become.

Why listen as a creator

The Brown-Winfrey interview demonstrates that the most interesting version of a famous conversation is often the corrective version: where someone who knows the research sits down with someone who helped popularize it and clarifies what was actually found.

Kara Swisher with Mark Zuckerberg (various Recode Decode episodes)
#11
Technology Interview

Kara Swisher with Mark Zuckerberg (various Recode Decode episodes)

Hosted by Recode Decode

Kara Swisher's repeated interviews with Mark Zuckerberg over the years produced the most sustained record of a technology leader's public positioning across a decade of crisis and controversy, with Swisher's refusal to accept non-answers as its defining quality.

Why listen as a creator

The Swisher-Zuckerberg body of work demonstrates that persistent questioning over multiple interviews reveals things no single interview can. Swisher's institutional knowledge of what Zuckerberg had said in previous years made her the only interviewer positioned to catch the inconsistencies.

Dax Shepard with Monica Padman (Armchair Expert)
#12
Friendship Interview

Dax Shepard with Monica Padman (Armchair Expert)

Hosted by Armchair Expert

Dax Shepard and Monica Padman's co-hosting dynamic produces interview conversations that demonstrate what genuine friendship and equal participation from a co-host adds to the interview format: a second perspective that the guest responds to differently than they respond to the primary host.

Why listen as a creator

Armchair Expert demonstrates that the co-host is an underutilized interview tool. Padman's questions often produce different answers than Shepard's because guests relate differently to her, and the dynamic between the two hosts is itself content that the guest responds to.

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