The best podcast episodes of all time? C’mon. How can you listen to 10 years’ worth of podcasts? Is something a podcast if it first aired on terrestrial radio? How do you weigh a rambling, bordering on chaotic comedy call-in show against an exquisitely edited and produced meditation on the nature of grief and the power of hallucinogens?
We’ll give you our answers to those questions in one second. But first a word from our sponsor … just kidding. First, our case for why this impossible task is worth attempting. Canons, so long as they are adaptable and expansive and ever evolving, are worthwhile things. They give you a sense of the possibilities of a form, a sense of what has (and hasn’t) been achieved. They give new artists in a medium places to start, examples to learn from, accomplishments to improve upon.
But what is a podcast? For our purposes, a podcast is a piece of audio that was created at least in part for digital release. If it was created for traditional radio, too, that’s fine, so long as the creators also made it with podcasting in mind. Podcast purists, if such people exist, might object to the inclusion of radio heavyweights, but This American Life and The Best Show, to take two major examples, are, to our minds, great podcasts as well as great radio shows. And when you dig into the other entries on this list, you’ll find the distinction blurs. There are not only radio shows that have become podcasts, but podcasts that have become radio shows. We decided to throw them all in together. (We left out, though, any Slate podcasts—though we’re proud of our work in the medium, it felt unseemly to include them on this list.)
How exactly does one judge a carefully crafted story that took weeks to report and put together but is only 15 minutes long against a 90-minute two-man back-and-forth full of digressions and absurdity with no real point? Well, you just do, basically. Which is better, The Simpsons or The Wire? I have no idea, but they’re both TV shows, and that’s a fun argument to have. When it comes to podcasts, we’re 10 years into a vivid, crucial artistic medium. The time to have such arguments has arrived.
25. Here Be Monsters, “The Grandmother and the Vine of the Dead” (2014)
Here Be Monsters is part of a recent wave of carefully produced, sonically sophisticated podcasts that tell surprising stories full of first-person reporting and adventurous editing techniques. Jeff Emtman says he created the show in order to face his fears, and since the show began in 2012, it has had episodes about hate groups, Juggalos, and slug orgies, among many other topics. But its best episode, we think, is this one, in which Lauren Stelling talks to an old boss called Cherub who, grieving the death of her best friend’s daughter, travels to a rain forest near the equator to take Ayahuasca, a powerful hallucinogen used by American Indian shamans. An interview with Cherub is surrounded by music, Icaro chants, and bird sounds; the effect is, well, trippy—but also surprisingly moving.
24. The Memory Palace, “Origin Stories” (2013)
On The Memory Palace, host Nate DiMeo tells short historical stories that are always moving and humane. This personal episode mixes nostalgia and humor in ideal measures. DiMeo recalls his time living alone in the house in Providence, Rhode Island, where his grandparents raised their daughters and delves into the family archive, which is stashed in boxes throughout the home. Most of the material is from his grandfather’s nightclub, the Club Baghdad, where his grandparents met. DiMeo searches for a mythical, long-lost recording of the floor show at the Baghdad—a record he is convinced will help his family come to terms with their grief over losing his grandfather—and doesn’t find it. Instead, we hear two modern-day podcasters (Maximum Fun’s Jesse Thorn and Jordan Morris) perform, in front of a live audience, comedy sketches that his grandfather wrote. It’s a consolation prize with a point: Even if some parts of the past are lost, there are others we can bring to life ourselves.
23. State of the Re:Union, “Bayard Rustin: Who Is This Man?” (2010)
On State of the Re:Union, host Al Letson usually takes an excursion to a particular American community. On this episode, he breaks from that format to introduce listeners to Bayard Rustin, the black, gay, Quaker pacifist who educated Martin Luther King in the principles of nonviolence and was the uncredited architect of the March on Washington. Rustin had an unconventional life that’s often omitted from histories of the civil rights movement, and the episode weaves together Letson’s musings on the meaning of Rustin’s work with clips from Rustin’s speeches and recorded interviews and, most moving of all, the voices with people who knew and were influenced by the man.
22. The Ricky Gervais Show, Season 1, Episode 7 (2006)
This early comedy podcast, distributed by the Guardian in 2005 and 2006, had its roots in a radio show hosted by British writers and comedians Ricky Gervais and Stephen Merchant. Picking up on one of that show’s running bits, the podcast focused squarely on their erstwhile producer, Karl Pilkington, whose stubborn dimwittedness soon made him an Internet celebrity (and the subject of much terrible fan art). In this particular episode, Karl tries to wash dishes without using his thumbs, says doctors should teach people to give themselves prostate exams, and shares his utter bafflement about the saying “a stitch in time saves nine.” Mostly it showcases the podcast’s signature dynamic: a disbelieving Gervais goading and mocking Karl, Merchant playing the supportive straight-man mediator, and Karl sitting at the center of it all, gloriously persistent and oblivious. For a long time, The Ricky Gervais Show was the most popular podcast in the world, and it introduced many people to the medium, showing them how funny and unexpected the format could be.
21. The Read, “Say No To F**k Boys!” (2013)
Hosts Kid Fury and Crissle anchor a weekly chat podcast that combines pop culture commentary, advice, and a weekly “read,” i.e., a cathartic rant deconstructing something that badly needs to be ripped apart. Fury, a blogger and YouTube personality, and Crissle, a writer, are friends with an easy conversational chemistry. Read episodes, including this one, are loose and chatty, featuring back-and-forth on ridiculous celebrities and their bad behavior, and occasionally reader mail; when Beyoncé surprised everyone with her December 2013 album Beyoncé, the hosts invited several friends on to simply share their instant, overloaded reactions. This installment features Crissle’s epic rant against what she calls “fuckboys,” weak men of bad faith who betray, manipulate, and mess with women. “Fuckboys” has become a recurring Read watchword, as well as a useful meme.
20. Seven Second Delay, “Andy Outbids the Tooth Fairy” (2005)
Seven Second Delay, with hosts Ken Freedman and Andy Breckman, is a live radio show that is also available as a podcast. Each episode is devoted to an on-air stunt. Ken and Andy take calls, needle each other, and relentlessly pursue the given episode’s stunt premise, sometimes into the realm of absurd unfunniness. Like Tom Scharpling’s The Best Show, also from WFMU, Seven Second Delay has accrued rabid fans and frequent callers. This particular episode’s stunt—Andy offers a princely sum to any kid who would bring a tooth into the studio by the end of the episode, instead of leaving it for the tooth fairy—ends in a suspenseful race to the finish line. Even among podcasts, the show feels incredibly loose—and more than most podcasts, Seven Second Delay conveys a strong sense of place and community. It feels local, without being provincial.
19. The Flop House, “Tango & Cash” (2012)
Why are there so many podcasts dedicated to talking about bad movies? Is it because teenagers who loved Mystery Science Theater 3000 reached adulthood just as podcasting arrived? Whatever the reason, the best of them is The Flop House, hosted by two Daily Show writers, Elliott Kalan and Dan McCoy, and fellow comedian Stuart Wellington. The three have a silly, improv-informed approach that suits well the idiocy they have generally just witnessed; many of their best moments come in ridiculous riffs that have nothing to do with the movie under discussion. The Tango & Cash episode is even more joyful than most, in part because Tango & Cash is a movie they actually like—it is what they call a “good bad movie,” i.e., an ideal topic for goofy, witty, delightful back-and-forth.
18. Strangers, “Love Hurts 3” (2014)
Producer and host Lea Thau’s show Strangers usually tells other people’s stories, but in this four-episode arc, Thau looks at herself, wondering why she has had trouble finding a new partner after suffering a life-altering heartbreak. The whole thing is raw and vulnerable and thoughtful in ways that are rare in any medium. Episodes 1, 2, and 4, which feel in equal measures excruciating and revelatory, feature Thau talking to men she’s tried to date since her breakup. In this third episode, she interviews two dating experts for advice. The first conversation, with an “expert” who doles out tired clichés, feels almost investigative: Thau doesn’t pull punches in questioning the author’s sexist conventional wisdom (though she is also very generous about things she thinks the supposed expert gets right). The second, with a much more sympathetic interlocutor, is cathartic, as Thau finally opens up about the experience that left her a single mom.
17. Comedy Bang Bang, “Time Bobby” (2012)
This improv podcast hosted by Scott Aukerman has now logged more than 300 episodes and boasts a huge cast of recurring characters (as well as a spinoff television show). The podcast illustrates how well character-based improv comedy works in an audio format: No costumes are necessary, and suspension of disbelief comes relatively easily. Episode 150 (also one of Aukerman’s favorites, at least as of 2012) features seamless character work done by podcast regular Paul F. Tompkins and SNL’s Bobby Moynihan. Taking the personae, respectively, of composer Andrew Lloyd Webber and the dangerous orphan Fourvel (like Fievel, but more “stabby”), Tompkins and Moynihan, aided by the always game Aukerman, spin a bizarre tale of adoption and murder. The “Time Bobby” concept turned out to be durable; the tale continued over two subsequent episodes of Comedy Bang Bang.
16. Dial-a-Stranger, “Life Savers” (2008)
Mercedes Martinez and Zachary Kent had a simple but ambitious idea: Ask people to submit their phone numbers, solicit questions from listeners, and then randomly dial those numbers and ask whoever answers one of those questions (along with more general queries about, say, how his or her day is going). The results were necessarily uneven, but the moments of serendipity captured the intimacy of podcasting like few other shows before or since. (Dial a Stranger is now sadly no more.) The episode “Life Savers” is a lovely example: Martinez and Kent ask five strangers, “Who saved your life?” Here’s the episode description in iTunes: “Julie was saved by Zach, Virgil was saved by his daughter, Melissa was saved by her step-mom, Angela was saved by her husband, and Dahlia was saved by her mother.” Don’t you want to hear those stories?
15. Filmspotting, “Episode 300,” Parts 1 and 2 (2010)
Adam Kempenaar and Sam Van Hallgren started Filmspotting in 2005, when podcasting was just getting off the ground. (It was called Cinecast at first and took the current name in 2006.) Over time, they established a reliably entertaining format: a review of a new film; then a self-consciously amateurish recitation of a classic movie scene, with listeners asked to identify the movie in question via email; then a top-five list, ranging from the “Top 5 Movies About Movies” (Episode 1) to the “Top 5 Movie Manimals” (Episode 507). They key to the show’s enduring success, though, is not the format so much as the tone: earnest, informed, self-deprecating, and conversational. Van Hallgren, now a producer of the show, turned co-hosting duties over to Matty Robinson, who in turn handed the reins to Josh Larsen in 2011. Each, along with Kempenaar, has sustained the show’s friendly enthusiasm and passionate devotion to new and classic movies, best exhibited, we think, on the 300th episode blowout, in which the hosts picked not just the top five but the top 20 films of the first decade of the 21st century.
14. Savage Lovecast, “109” (2008)
I started listening to the Savage Lovecast right about the same time that I came out, so advice columnist Dan Savage’s weekly doses of sex and relationship guidance and liberal polemic has been a constant companion for literally all of my sexual life. A particularly fine example of the Lovecast is Episode 109, which was recorded just after the passage of California’s anti-gay Proposition 8. Savage starts the program with one of his typical political rants, but with added passion given the news—he offers the Mormon church a generous “fuck you” for their efforts, noting that “when political attacks are launched from churches, political responses will be delivered to churches.” He then moves on to listener questions, a trademarked balance between poignant relationship worries and comically specific sexual issues (like one caller’s “smelly dick”). Then, as usual, the show ends with listener comments, which this time focus on responses to Prop 8; it feels like a cathartic group therapy session. And that feeling of community, of not being alone with your fears or problems or disappointments, is why I keep tuning in all these years later. —Bryan Lowder
13. Soul Music, “Don’t Leave Me This Way” (2013)
The BBC Radio 4 show Soul Music investigates the emotional resonance of famous pieces of music. This installment, about the song “Don’t Leave Me This Way,” which was first performed in the early 1970s by Harold Melvin and the Blue Notes, with Teddy Pendergrass on vocals, features a trio of interwoven segments about death, loss, and faith. The episode connects the stories of Pendergrass, who was paralyzed in a car accident at age 42; the gay community in the U.K., which danced to a remix version of the tune while mourning the loss of friends during the AIDS crisis; and Sharon Wachsler, homebound by illness, who turned to the song during dark times. The song itself, heard in its different recordings throughout the episode, gains layers of meaning, becoming more haunting and beautiful each time we hear it.
12. Love + Radio, “Secrets” (2006)
Nick van der Kolk’s Love + Radio is a podcast pioneer, taking the personal storytelling and high-quality production you might associate with This American Life into realms more risqué and even raunchy than you’re likely to find on public radio (though some episodes have, in fact, aired on public radio). The show has done episodes about a Detroit man running a strip club in his home and a woman who performed in balloon fetish videos, among many other subjects, winning multiple awards in the process. There are several episodes we might have chosen, but we like this early one, which tells stories about secrets, including one about the then quite new PostSecret project.
11. The Best Show on WFMU with Tom Scharpling, “Dec. 14, 2010” (2010)
At the start of this episode of the long-running, cult-favorite call-in show, musician Aimee Mann, a regular guest, takes a call from her fan “’80s Rick.” “Ms. Mann,” he starts, “I wanted to say that I really loved what we did in my dream last night.” Before host Tom Scharpling can stop the caller, phrases like “a wire feather duster” and “burnt urine” creep out among an explosion of bleeps. The rest of this episode is just as off-the-rails, taking the shape of a bizarro holiday party. Tom and guest John Hodgman gulp Four Loko, while a sober John Roderick looks on in disbelief. Unlike the colorful malt liquor drink, the new incarnation of The Best Show won’t be missing essential ingredients. —Andrea Silenzi
10. Welcome to Night Vale, “Pilot” (2012)
Choosing a single episode of Welcome to Night Vale is difficult, since one of the show’s greatest strengths is the long-term world-building it’s done over its 57 episodes. Created by Joseph Fink and Jeffrey Cranor, Night Vale is a sprawling fictional series narrated by an unnamed radio host set in a small town located at the hellish nexus of all things sci-fi, fantasy, and horror. What makes the pilot particularly notable, then, is the confidence and certainty with which it presents this world from the very beginning. Jumping straight into such a fully realized, high-concept world of cosmic horror from the word go is no easy feat, but this episode somehow manages it with poise. —Chris Wade
9. The Moth, “Franny’s Last Ride” (2009)
The Moth began organizing live storytelling events in 1997. Eleven years later, they began turning recordings of those stories into podcasts. Few are as heartrending and eloquent as the one told by Mike DeStefano in 2007, which was released as a podcast in 2009. DeStefano, a comedian who died of a heart attack in 2011, talks about his life with Fran, whom he met in rehab when he was trying to kick heroin. Fran was diagnosed with AIDS after they started dating and before they got married. When she was in a hospice, shortly before her death, he bought the Harley-Davidson they’d always wanted and took her on a ride. “I always imagined the wind on a bike making you feel free, you know?” DeStefano says. “It’s so powerful. For 10 minutes we were normal, and that wind just blew all the death off of us. … Nothing I’ll ever do will be that grand.”
8. The Dead Authors Podcast, “Walt Whitman, Featuring James Adomian” (2013)
The Dead Authors series, recorded live, features host Paul F. Tompkins—a podcast savant whose own Pod F. Tompkast also threatened to make this list—in the character of H.G. Wells. The conceit of the show is that Wells has whisked deceased favorites to the present day in his time machine. The authors, played by other comedians, submit to interviews, with varying results. James Adomian’s Walt Whitman is the best of the bunch. Never breaking character, Adomian responds to every question from Tompkins’ courtly Wells with a stream of Whitmanic prose. He stays in cadence, sticking with Whitman’s themes, spouting forth grandiose and nonsensical catalogs, only rarely finding himself at a loss for words. It’s a perfectly sideways interpretation of the poet’s signature style.
7. Radiolab, “Space” (2004)
Radiolab, like This American Life, is a gateway podcast, hooking listeners with a rich, 13-season back catalog of episodes that stand the test of time. “Space” was one of the first Radiolabs to have been produced during the podcast era, and the episode brings together many of the elements that make people love the show: interviews with a diverse slate of voices, scientists as well as artists and authors; an intriguing soundtrack (“Radiolab space episode music” is a Google search autofill); and, above all, an intelligent probing of the human, emotional aspects of an essential scientific topic. The most indelible part of the episode is the interview with Ann Druyan, widow of Carl Sagan. She tells the story of the pair’s collaboration on the “Golden Record” sent with the Voyager probes, a job they started as colleagues and finished as lovers.
6. 99% Invisible, “The Sound of the Artificial World” (2011)
Some 99% Invisible episodes make me crave a visual supplement. (What did the lost walled city of Kowloon look like?) But in this episode, Roman Mars’ beloved short-form design podcast asks how sound designers make “organic sounds for inorganic things.” The clicks, sproings, and clatters that sound engineer Jim McKee demonstrates for Mars are the background noise of everyday life for people who use digital devices. The episode singles these sounds out for analysis and deconstructs their origin, a classic 99% approach that works beautifully. You may find yourself looking toward your phone several times during the episode’s five-minute run, thinking you’ve received a text—a weird overlap of podcast and life that makes the episode’s point perfectly.
5. Hardcore History, “Ghosts of the Ostfront” (2009)
The four-part Hardcore History series on the Eastern Front of World War II is almost five hours long. And that’s short for a Hardcore History “episode.” The show’s fall of Rome arc, “Death Throes of the Republic,” clocks in at 13 hours. The subject matter of “Ostfront” lets host Dan Carlin do what he does best: paint vivid pictures of a terrible time in history. Walking listeners through Operation Barbarossa, the German attempt to capture Moscow, the Battle of Stalingrad, and Germany’s ouster from the Soviet Union, Carlin is a wide-eyed, colorful guide to a dreadful story.
4. Serial, “The Alibi” (2014)
Have you heard about Serial? It’s pretty good. It’s so good, in fact, that there are podcasts about this podcast—and its success has helped to create momentum for the entire medium. That has happened in part because, by telling a true story over 12 episodes of roughly 45 minutes each, and continuing to report that story as they go, the producers of Serial have created something genuinely new and expanded people’s notions of what podcasts can do. It helps, of course, that the story they’re telling, about the murder of a young woman in Baltimore in 1999 and the questionable conviction of her ex-boyfriend for the crime, is immediately gripping. But more important is the care with which they tell that story, from the reporting, to the music, to the eloquent but conversational narration by host Sarah Koenig. And it’s all there in Episode 1, “The Alibi,” which is now one of the most downloaded podcasts ever made.
3. Radio Diaries, “Strange Fruit: Voices of a Lynching” (2010)
This 2010 episode of Radio Diaries was rebroadcast this year after the killing of Michael Brown in Ferguson, Missouri, and the ensuing protests. The show uses long-lost historical audio to tell the story of the lynching in Marion, Indiana, that inspired poet Abel Meeropol to write the song “Strange Fruit.” The producers juxtapose voices of the witnesses who stood by while a crowd hanged the black teenagers Thomas Shipp and Abram Smith on Aug. 7, 1930, with a 1994 interview with James Cameron, who barely escaped being the third victim. The host, Joe Richman, makes minimal interventions after setting the initial scene, leaving a historian, those eyewitnesses, and Cameron’s steady voice—“I was pleading for some kind of mercy, looking for a kind face”—to speak for themselves.
2. This American Life, “The Giant Pool of Money” (2008)
This episode about the 2008 financial crisis was a collaboration between NPR News and This American Life, a weekly public radio show that has become the 800-pound gorilla of podcasting. It spurred, in turn, the creation of Planet Money, an excellent NPR podcast about business and economics. The hourlong episode traces the collapse of the housing market to its earliest roots and is incredible for its ability to make complicated financial topics completely understandable. Wondering about a mortgage-backed security? A collateralized debt obligation? A subprime mortgage? Alex Blumberg and Adam Davidson explain all of this with ease. You'll be hard pressed to find a better synopsis of what brought down the economy in 2008 anywhere. —Alison Griswold
Marc Maron’s two-hour-plus conversation with Louis C.K. is one of the best interviews you’ll ever hear, providing genuine insight into the mind and career of one of the world’s great comics, as well as thoughtful meditations on success, failure, friendship, and fatherhood. On top of all that, this episode, for someone who’s listened to a lot of podcasts, feels almost like a coming-of-age moment for the form. Maron started his podcast at a professional low point, out of a kind of desperation. When he first began recording WTF, he was sneaking into the studios of the radio station that had just fired him (and not for the first time), putting something out into the world via this new independent medium because he wasn’t sure what else to do. And then a following grew. Maron was self-consciously bitter about his professional disappointments, and many of his conversations were with more successful peers; though it wasn’t a stated goal of the podcast, you could detect in the early episodes Maron working out some of his resentments and coming to know himself better through the frequently intense talks with fellow comics. This all came to a head in the episode with C.K., whom Maron had known for more than two decades and who had become widely acknowledged as the best stand-up in the country. When the second part was over, it was clear not only that WTF was a wonderful thing, but that podcasts themselves were a remarkable form.