The 22 Best Podcasts of 2019

January 2, 2020 9:40 am

Fine, it’s technically 2020 now. However, all those other “best of” lists that came out before the new year aren’t truly covering the whole year. What if some amazing podcast came out on December 28th? Their list wouldn’t be validated. Or, maybe I procrastinated a little too much this year and took some extra time revisiting some podcasts to create my best podcasts of 2019 list. Yeah, that’s what happened.

As with any “best of” list — especially those written by a single person (like this one) — there’s a decent amount of subjectivity as indivudual’s tastes vary drastically. I feel like this is magnified in the world of podcasts. So given the obligatory disclaimer, my best podcasts of 2019 list is through my lens. I tend to skew towards newer podcasts — or those who made a substantial leap this year — and run the spectrum of indie to mainstream.

If you’re looking for a more comprehensive list that takes into account multiple interests and opinions, read our list from midyear, The Best Podcasts of 2019 (So Far). Also, while I’ve got your attention, here’s my list from 2018 and the requisite 2018 midyear collective list.

2019 continued to push the boundaries of what’s possible in podcasting, from a creative and quality perspective. As always, podcast stalwarts like This American Life, Radiolab, Criminal, Reply All, and others are deserving of every accolade thrown their way. That said, I didn’t include them on my list, opting to go with newer and less known podcasts.

End of the preamble, here are my best podcasts of 2019 — in no particular order — along with some honorable mentions.

Running From COPS

Dan Taberski continues his elite storytelling run and is in my short-list for podcasters I’ll auto-subscribe to their new work, whatever the subject (see: Trufelman, Avery in the recommendation below). After the successes of Missing Richard Simmons and Surviving Y2K, Taberski focused his next Headlong installment on the long-running TV program, COPS, and the troubles with how police action and crime is portrayed.

Listen: Apple Podcasts | Stitcher | Spotify

Nice Try! Utopian

As I alluded to in the Running From COPS paragraph, we can go ahead and pencil in whatever new project Avery Trufelman is working on for the 2020 list. In the midyear roundup, Nice Try! Utopian was recommended by true podcast tastemakers, Wil Williams, Paul Bae, and Zack Kahn — something that shouldn’t go unnoticed.

As Trufelman tested (and found success) with her 99PI spin-off mini series, Articles of Interest in 2018, she took a similar concept to found a standalone project. Nice Try! Utopian is a seven-episode series covering design failures in utopia attempts. As Kahn succinctly reviews, “Trufelman leverages the expansive canvas of longform narrative audio to paint a rich, color portrait of attempts to try and design a better world, and what happened when those designs didn’t go according to plan.”

Listen: Apple Podcasts | Stitcher | Spotify

Dolly Parton’s America

Host Jad Abumrad explores country music icon, Dolly Parton’s impact on American and global culture, her life and her worldview. He finds that Dolly Parton’s fan base is a cross-section of American demographics, and he embarks on a quest to answer why.

Jad’s interviewing showcases Dolly Parton’s charm and no-nonsense approach to song writing. She laments about the darkness in her early music while still being able to laugh about it. “I used to write a lot of sad-ass songs,” she tells Jad. Sound clips of her music and wisdom drape nine episodes that explore the “Dollyverse.”

Dolly Parton’s song “9 to 5” was an anthem to women’s empowerment. In the episode Dollitics, Jad delves into Dolly Parton’s relationship with politics, how she manages risk, and seems to “circumvent disaster.” Her “verbal judo” has kept her afloat in an age of deep political polarization. What connects with people is her genuineness, down-to-earth-nature and big heart.

The show is not without critique. Writer and editor, Aisha Harris, states in an interview that even good-hearted people have blind spots. What is so refreshing is Dolly Parton’s response to the controversy surrounding Dixie Stampede.

Dolly Parton’s America will reward and satisfy her biggest fans, and convert new ones.

Listen: Apple Podcasts | Stitcher | Spotify

StartUp

The first season of StartUp documented Alex Blumberg’s post-This American Life entrepreneurial project which would later become podcast studio success story, Gimlet. It was an expertly-narrated meta look into the difficulties of podcasting and starting a business.

I didn’t find any subsequent season of StartUp to be all that fascinating.

Then in February, the news broke Spotify would be acquiring both Gimlet and podcast hosting company, Anchor. Many hoped Blumberg and co-founder Matt Lieber would give a similar behind the scenes documentary into the acquisition, and they delivered. The final season of StartUp provides a truly honest view into the difficulties of podcasting at scale, dealing with start-up growing pains including financial and inter-personal issues, and ultimately what led to them selling to Spotify.

Listen: Apple Podcasts | Stitcher | Spotify

All Fantasy Everything

I wrote in a CBC round-up that All Fantasy Everything is my guilty pleasure podcast and two paragraphs later Jody Avirgan mic dropped the term out of existence, ”you should never feel guilty about the things you like.”

The truth is, however, AFE leveled up in 2019. 150+ episodes later, and the comedy improv show about fake drafting obscure items like Tom Hanks movies, things you say after you dunk on someone, or the perfect sandwich has nearly perfected what I’d look for in a comedy podcast.

This year, they produced what I’d consider their best episode, Disney Songs with guest Katie Nolan. The core crew has an unrivaled rapport and their ability to integrate guests make for a super fun listening experience and more than a couple laughs.

Listen: Apple Podcasts | Stitcher | Spotify

Spectacular Failures

Following the success of How I Built This, it seemed like there was a mad dash for entrepreneur interview podcasts. You know what’s even more interesting than rich people talking about their success? Stories of failures.

Executive Producer of Radiotopia, Julie Shapiro, wrote a review of Spectacular Failures in our midyear round-up, “While other pods have taken on the culture of failed business and ruined legacies, none have done so with the particular spirit and chummy schadenfreude that Lauren Ober brings to Spectacular Failures. The show features stories you’ll realize you’ve been wondering about for years, as soon as you read the episode titles: “Schlitz Beer goes bad, then worse,” “Kodak misses its moment”, etc.”

Listen: Apple Podcasts | Stitcher | Spotify

Uncover

Award-winning Uncover spans five seasons of compelling and chilling story-telling. Each season is hosted by a different journalist as they investigate Canadian and international crime mysteries. People closely connected with the topics at hand will often get emotional when they recount the horrors experienced or mourn the loss of loved ones.

Dark themes are explored by CBC Podcasts through the exposé of the cult NXVIM (pronounced “Nexium”) in Season 1: Escaping NXVIUM, the unsolved case of 1965 Canadian Pacific Airlines Flight 21 in Season 2: Bomb on Board, a serial killer that targeted Toronto’s gay community dating to 1975 in Season 3: The Village, the 1998 disappearance of 77-year-old woman Joan Lawrence in Season 4: The Cat Lady Case, and the homicide of Toronto teen Sharmini Anandavel in Season 5: Sharmini.

Journalists Josh Bloch, Ian Hanomansing, Johanna Wagstaffe, Justin Ling, Zander Sherman and Michelle Shephard tackle unresolved questions in their individual styles.

To cherry-pick a few moments from such a wide-scope, a tape-recording of Sharmini’s voice in S5: E6 is particularly haunting, Season 1’s Sarah Edmondson’s realization of abuse in her community deeply disturbs, and Chuck Shaw-MacLaren’s eyewitness account of Canadian Pacific Airlines Flight 21 crash as an ambulance driver grips the listener. Stories that he had kept to himself for 50 years tug at the heart strings. “I’m talking more to you, than I have to anybody,” he admits after he takes host Johanna Wagstaffe’s hand.

Uncover peers into the tragedies and trauma caused by unsettled mysteries.

Listen: Apple Podcasts | Stitcher | Spotify

ESPN 30 for 30 The Sterling Affairs

Sometimes I think the ESPN brand actually holds back the 30 for 30 podcast from a larger audience. Sure, the podcast focuses on stories with a sports angle, but simplifying the podcast into a narrow category does a disservice to its excellent documentary storytelling ability. Though their individual contained episodes are often wonderful, I think the podcast is at its best when it’s given a couple episode mini-series. Last year, their Bikram series made my best of list, and this year they went back to the well with a season focused on disgraced former NBA owner, Donald Sterling.

Listen: Apple Podcasts | Stitcher | Spotify

BROKEN: Jeffrey Epstein

Before we hit “peak Epstein podcasts” (related: peak impeachment podcasts), BROKEN hit the scenes combined with seasoned journalists (The New Yorker’s Ariel Levy, The Miami Herald’s Julie K. Brown), with podcast studio Three Uncanny Four Productions and Oscar-winning director Adam McKay.

There may be some fatigue around the subject matter, however, BROKEN is a riveting six-episode series detailing Epstein’s history, rise of his monstrous empire, and eventual arrest and death.

Listen: Apple Podcasts | Stitcher | Spotify

1619

The New York Time’s foray into podcasting has been an unbridled success on every level. Last year’s limited series, Caliphate, was my personal pick for best podcast of the year. This year, they produced a five- (really, six-) episode miniseries about the history of the US and the slave trade.

Hosted by Nikole Hannah-Jones, the podcast gives an excellent history and insight into America’s civil liberties problems and institutional racism.

Listen: Apple Podcasts | Stitcher | Spotify

Mobituaries

Mo Rocca applies his love for obituaries in pieces that explore the lives of people that have inspired him. Funny and inquisitive, Mo Rocca’s experience as a correspondent on The Daily Show and CBS Sunday Morning helps structure well-paced narratives. His journalistic integrity and approach stand out. Mobituaries weaves interviews with experts and enthusiasts, poll questions, and elements of film, music, and television to great effect. What results are compelling stories that shine a light on forgotten historical figures and aspects of household names that are not common knowledge.

In the episode Thomas Paine: Death of a Forgotten Founding Founder, Mo Rocca asks Anthony Salvanto, CBS News’ Director of Elections and Surveys, “If there would have been no Thomas Paine, there would be no ‘what’?” His questions open up in-depth conversation that relates to the world we live in today.

In The Black Congressmen of Reconstruction: Death of Representation, the sounds of the Charleston Harbor backdrop a riveting tale of enslaved seaman, Robert Smalls’ great escape into the Union Blockade. Mo Rocca’s exchange with Michael Bouleware Moore, Robert Small’s great-great-grandson, provides a personal touch and reminds us that we are not too far removed from the age of slavery.

History buffs and curious minds will appreciate Mobituaries and Mo Rocca’s enthusiasm for forgotten knowledge.

Listen: Apple Podcasts | Stitcher | Spotify

The Rewatchables / The Rewatchables 1999

Another podcast entry that’s nowhere near new but one that seems to get stronger the more episodes they do. The Ringer expanded their partnership with Luminary and created a spin-off podcast solely focused on movies that came out in 1999. Besides the narrowed scope, the two podcasts are essentially identical.

If you’re unfamiliar, The Rewatchables is a movie podcast which analyzes and mostly celebrates past movies. Their vibe is very much “friends watching on the couch” but mixed with insights, jokes, and genuine fun. The Rewatchables at least partially makes this list for their episode on Old School, which single-handedly forced me to end a workout early because I was crying laughing and in no shape to even stand up.

The Rewatchables Listen: Apple Podcasts | Stitcher | Spotify

The Rewatchables 1999 Listen: Luminary

Gay Future

We’ve covered audio drama and fiction podcasts extensively on this site, but it truthfully needs to be repeated ad nauseam: the most creative and ground-breaking work in podcasts is being done in the audio drama genre. The Allusionist’s Helen Zaltzman perfectly sums up the appeal of Gay Future, “In a long-lost YA novel by Mike Pence, it’s 2062 and, under the totalitarian regime ruling North America, everyone is gay. Except one schoolkid… This show is so funny; the acting is on point and the production is great. I had such a blast listening to this caper.”

Listen: Apple Podcasts | Stitcher | Spotify

Slow Burn

Slow Burn’s future seemed uncertain after the creator, Leon Neyfakh, left Slate to start a new podcast exclusive to Luminary (see: FIASCO below). The first two seasons covered the political climate and delved into the respective impeachment processes for Presidents Nixon and Clinton. The third season, however, takes a departure from the traditional political genre and instead covers the infamous feud and eventual deaths of rappers Tupac and Notorious BIG.

Though the chosen topic is a departure, fortunately that’s the extent of the differences of the podcast in the post-Neyfakh era. The interviews, analysis, and overall documentary narrative are among the best examples in podcasting today.

Listen: Apple Podcasts | Stitcher | Spotify

Switched on Pop

With both AFE and The Rewatchables I mention they sort of leveled up this year. In Switched On Pop’s case, which started in 2014, this is especially true. Media giant, Vox, picked up the podcast earlier this year and the show was exposed to a much larger audience.

Hosted by songwriter and music journalist, Nate Harding, and musicologist, Nate Sloan. Together they have both an expanse of knowledge and the chemistry to make a truly entertaining and informative podcast.

Listen: Apple Podcasts | Stitcher | Spotify

The Dropout

The Dropout opens with Elizabeth Holmes, once Silicon Valley’s youngest female self-made billionaire, taking an oath for her testimony on July 11, 2017 on nine criminal charges of wire fraud and two counts of conspiracy to commit wire fraud. In six episodes that range from 39 to 47 minutes, host Rebecca Jarvis unfolds a story of unbridled ambition, gratuitous ethics violations and the culture of celebrity.

Elizabeth Holmes and her blood-testing company, Theranos, were poised to become the “Apple of healthcare.” Rebecca Jarvis’s thorough journalism and interviews are weaved in the style of a true-crime drama. She delivers the story as a reporter, and manages to remain an objective narrator.

Theranos’s promise to conduct a myriad of tests from a single pin-prick of blood was lofty, but with Elizabeth’s business savvy, charm and cunning she was able to convince investors of her product. The allure of working with the then world’s youngest self-made female billionaire is honed in on the episode A Star Is Born. Jared Leto introduces Elizabeth at the 2015 Glamour Women Of The Year Awards, and Bill Clinton sings praises as he assures a captive audience that “We’re in good hands.”

Join Rebecca Jarvis as she unravels the rise and fall of Elizabeth Holmes in a stark commentary on fame and corporate greed.

Listen: Apple Podcasts | Stitcher | Spotify