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The Best Podcasts of 2021

Give the music a rest and get into the conversation around sports, pop culture, and more.

By Emma Carey and The Esquire Editors
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Every product was carefully curated by an Esquire editor. We may earn a commission from these links.

Since the podcasting dawn (in the early aughts), the medium has come to occupy a unique area of real estate within the media landscape. For some, it’s a daily commute lifesaver; for others, a primary resource for news gathering. Covering just about every topic, from sex to true crime, the podcasting world is seemingly neverending.

Amongst the outliers of self-indulgent podcasters are loads of incredibly smart, funny, friendly, and talented voices that deserve to be heard. Whether you’re looking for a way to brush up on some history while on the go, want to open your perspective on the world around you, or just want a little extra company throughout your day, there’s absolutely a podcast out there that’s right for you. Probably more than one. Probably a ton of series to binge.

The beauty of podcasts is that there are infinite ways to listen. And we’ve been mapping the best of the best, across a myriad of niches, for our 2021 roundup, with some brand-new gems and tried and true staples for good measure. So plug in those earbuds and get listening.

These are the best podcasts of 2021.

Once Upon a Time... at Bennington College

once upon a time at bennington college
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In 2013, Lili Anolik started reporting the story that would consume the next decade of her life. This was the story of Bennington College, a "particular and improbable" university for rebels, heiresses, and artists in rural Vermont. In the 1980s, the Bennington experience proved to be a formative chapter for many great artists, including legendary Gen X writers like Bret Easton Ellis, Donna Tartt, and Jonathan Lethem. In 2019, Anolik's reporting coalesced into an Esquire feature: "The Secret Oral History of Bennington: The 1980s' Most Decadent College." Now, Anolik has expanded the story in a podcast that explores the secret histories of these three great writers, their career-defining works, and Gen X itself. In these riveting episodes, Anolik speaks with dozens of alums to understand how Bennington allowed these young writers to mythologize their collegiate experience—and mythologize themselves. —Adrienne Westenfeld

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Anthony Bourdain: Parts Unknown

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For years, viewers across the globe have lived vicariously through Anthony Bourdain’s many adventures on Parts Unknown. Bourdain embraced life in a way many of us could only dream to do. And, now more than ever, his lifestyle—moving freely about the world and taking in new cultures with an open heart, empty stomach, and mask-less mouth—truly seems like a pipe dream. Luckily, CNN’s latest podcast revival of the series now allows us to revisit Bourdain’s trips with a whole new perspective.

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9/12

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20 years later, the impact of 9/11 is still being parsed. And in Pineapple Street Studio’s 9/12, Dan Taberski argues that the day after the attack is when the world truly changed forever. From conspiracy theories to murky ethics of satire, each episode of 9/12 uses a different person’s perspective to discuss one of the many cultural products to emerge in the wake of 9/11.

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Black Cancer

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An episode of Jodi-Ann Burey’s Black Cancer feels like both a personal conversation between old friends and breakthrough research being read aloud. A large part of this is because many of the stories Burey has chosen to spotlight are some of the first of their kind to receive a mainstream platform. After witnessing firsthand the way that medical racism has excluded people of color from conversations about cancer (and often prevented them from receiving proper screenings and treatment), Burey became determined to promote the stories of those who have been impacted by the disease. The result is a collection of stories from a variety of perspectives—including survivors, family members, and care takers—about what their cancer journey means to them.

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Dysfunctional Family Storytime

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There’s truly no place like home for the holidays. Especially if it’s a broken home. Luckily, podcasting giant Gimlet has summoned its inner middle-child-mediator to guide you through tense family gatherings for the end of the year. (Or, to at least give your misery some company.) Curated by Jorge Just, the series offers a collection of previously-aired episodes from various Gimlet series covering everything from dinner table discourse to secret sibling sagas. If you and your folks are tired of the cookie-cutter families in holiday movies, this series will feel like your chosen family.

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Oprah's Super Soul

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It’s no secret that, among her many hyphenates, Oprah Winfrey has a knack for bringing out a never-before-seen side of her interview subjects. Her podcast is no exception. Super Soul is an interview series with a special focus on spiritual awaking featuring a myriad of influential guests. I’d give you a list of the big names, but the best way to sum it up is: Who would say no to Oprah?

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Keep It

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If you’re looking for a pop culture pod with a bit more substance, look no further. Hosts Ira Madison III, Louis Virtel, and Aida Osman have a way of making their episodes feel like a celebrity gossip chat happening between a group of close friends. (That is, if your close friends circle included three hilarious people with a nearly academic grasp on the pulse of pop culture—along with a periphery circle of friends including the likes of Jane Fonda, Ronan Farrow, and Kimberlé Crenshaw, to name a few.) In our information overloaded society, what makes this one stand out is the hosts’ keen ability to find a lasting significance behind the fleeting buzzy topics of pop culture. With an emphasis upon entertainment’s intersection with politics and society, each outing is sure to leave you with a broadened understanding and appreciation of pop culture—and plenty of quotable one-liners thrown out by its hosts.

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Las Culturistas

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Sure, Las Culturistas has been around since 2016. But, as shown by the podcast’s recent Las Culturistas Culture Awards (where categories included everything from “Best Movie We’ve Never Seen” to “Smallest Snub”), the series is always giving us something new to love. Hosted by comedians Bowen Yang and Matt Rogers, “Las Cultch” welcomes a slew of hilarious guests to discuss their formative pop culture memories and other current happenings. Come for the culture—which you’ll quickly learn is liberally applied term—stay for the “I Don’t Think So, Honey” rant segment.

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Sunday Scaries by Headspace

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Whether your Sunday afternoons typically look like pre-work preparation, post-drinking rumination, or both, it’s not uncommon for those final hours of the weekend to become synonymous with stress. And, with just two measly off-days granted to most of us 9-5ers each week, it’s about time we reclaim our rest day. Enter: Sunday Scaries from Headspace. Each week, host Dora Kamau offers a new mindfulness prompt to recenter listeners before the week ahead. With bite-sized episodes typically ranging around five minutes, it’s the perfect way to start working meditation into your routine without making it feel like yet another chore on your checklist.

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Ear Hustle

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The first podcast series to ever be produced inside of a prison, Ear Hustle shares the everyday stories of those currently living inside of San Quentin State Prison, as well as the formerly incarcerated. From personal narratives to historical accounts, Ear Hustle covers a wide variety of nuanced, candid accounts about life during and after prison.

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Poog

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If you’re like just about every human in modern-day society, there’s a good chance you’ve fallen headfirst into the rabbit hole that is the wellness industry. It will chew you up, microneedle you, spit you out, and take you as a probiotic shot before it spits you out again. But fret not: Comedians and best friends Jacqueline Novak and Kate Berlant have been there, too. And they have thoughts. Enter: Poog (like Goop, get it?), Berlant and Novak’s brainchild of hilariously analytical musings about the wellness industry. Put down that vision board and cleanse yourself with the elixir of laughter.

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Through the Cracks

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Hosted by Jonquilyn Hill, Through the Cracks investigates the unsolved 2014 disappearance of Relisha Rudd - a second grader in Washington D.C., who was not declared a missing person until 18 days after she was last seen at her homeless shelter and at school. Unsatisfied with the unjust handling of Rudd’s disappearance, Through the Cracks asks who our society looks out for, who falls through the cracks, and why.

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Spectacle: An Unscripted History of Reality TV

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Before you scoff at the near mention of reality TV and its plebeian appeal, hear us out for a second. Whether you like it or not, reality television is arguable one of the most fascinating, and influential, cultural products of American media. And host Mariah Smith is here to give us a whole new perspective on the history and significance of reality TV as we know it in the new series Spectacle. A must-listen for reality TV fans and haters alike, Smith unveils the intersections of politics, culture, and reality TV in an episode-by-episode format that’s as bingeable as Love Island.

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ezra klein show
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Vox co-founder Ezra Klein’s beloved biweekly podcast has found a new home at the New York Times this year. The series is, as Klein describes, a “conversation show” where Klein sits down with some of the leading experts in the world to pick their brain on the topics that matter most: from climate change to psychedelics and beyond.

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Anything for Selena

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Reporter Maria Garcia offers an impactful look at the life, death, and legacy of beloved Mexican-American entertainer Selena in the new series Anything for Selena. Driven by her personal connection to Selena since growing up as a Mexican-American herself, Garcia’s deep reverence for the artist makes for powerful storytelling when matched with investigative reporting on the work and political significance of Selena.

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Resistance

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The inspiration for Resistance came to its host Saidu Tejan-Thomas, Jr., in the summer of 2020 amidst worldwide Black Lives Matter protests. Noticing a new generation of activists and organizers emerging, Tejan-Thomas says his first question was, “How are they going to keep this up?” What came from this idea is Resistance, a podcast series driven by first-person narrative experiences of Black and Brown people “refusing to accept things as they are.” Tejan-Thomas and his team bring a deeply personal aspect to today’s news and headlines, incorporating the stories of those on the front lines of social progress—and Tejan-Thomas’s own personal history—into each episode.

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Death, Sex, and Money

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As the title might imply, Anna Sale’s WNYC series Death, Sex, & Money doesn’t shy from discussing the things we think about the most and talk about the least. From near-death experiences, to one night stands, the student loan crisis, STIs, alcoholism, and whatever else life throws at us, Death, Sex, & Money has a no holds barred approach to its topics. And, with this, comes a deep journey of vulnerability and honesty between Sale and her guests, who range from movie stars to Supreme Court justices to everyday people. It’s messy, freeing, uncomfortable, tender, and, at its core, as human as it gets. If you have a love for storytelling, tend to muse about life, or are in need of a push into more vulnerable conversations, Sales is the perfect guide to get you there.

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Louder Than a Riot

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Since its arrival in 2020, Louder Than A Riot’s urgency has grown louder than ever before, with hosts Rodney Carmichael and Sidney Madden delivering some of the most incisive and pertinent investigative journalism in the podcast game. Using the lens of hip-hop to analyze the mass incarceration in America, each episode reflects upon a different hip-hop artist’s story in order to dig deeper into the criminal justice system. The series comes complete with a playlist of the songs used in each episode as a tool for analysis, and features an inside look at the music industry, prison industrial complex, and their intersections in a way that is as thoughtful as it is impactful.

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StraightioLab

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As any intellectual will tell you, we don’t give straight culture enough attention. Sure, many would say we live in a heteronormative society where straightness is baked into the very infrastructure of our world … but, what even is being straight? What does it look like? What do we talk about when we talk about being straight? Self-identified “smart comedians” George Civeris and Sam Taggart have stepped up to fill this gaping hole in the hetero-canon with the ethnography that is StraightioLab: a series that aims to “unpack the rich, multi-colored tapestry of straight culture.” One scroll through its episode titles packs comedic effect in itself, with everything from “Pictures with Siblings,” to “Wearing PJs to Run Errands,” and, of course, “Reading” making their way onto the list of all things straight. With a roundup of beloved alt-comedy guests, and segments like “Straight Shooters,” StraightioLab is the perfect series to listen, learn, and laugh your way to becoming a straight culture aficionado.

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The Laverne Cox Show

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Looking to become a better person? Expand your mind? Listen to the hypnotic voice of Laverne Cox? You can accomplish all three of those things in one place: The Laverne Cox Show. The new podcast from Shondaland and iHeartMedia lets Cox take the reins, allowing her to facilitate conversations around topics ranging from fatphobia to dating in mid-life. Fearless and candid, Cox mixes charm with candor on a podcast where nothing is off limits. - Justin Kirkland

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