The Best of 2021: Podcasts

Dave Wheelroute
Saoirse Ronan Deserves an Oscar
18 min readJan 23, 2022
Image from Athlete Speakers

“I was just starting to get it. I was about to get an answer right, everybody.”

What a year for podcasting! So many different shows, so many different episodes. So many trends, theme song changes, network changes, host changes, and more! Podcasts remain close companions of those who choose to listen to them. Accompanying us on travels, commutes, nighttime rituals, and more. When you never want to be alone with your thoughts, podcasts are there!

I also went through a bit of a culling with my own podcast feed. I stopped listening to Entertainment Weekly’s The Awardist podcast because I found myself enjoying the Oscars and Emmys coverage more from Vanity Fair’s Little Gold Men. I tapped out of Book of Basketball 2.0 when it became an oral history on Len Bias and out of Clear + Vivid with Alan Alda when it became a coronavirus check-in station. I stopped listening to 10 Minute Teacher Podcast when I realized I never wanted to think of teaching in my free time. Scriptnotes stopped having interesting interviews, The Director’s Cut became spoiler-ridden for movies that were months away from release, What’s on Disney Plus and Popcast became insufferable. Karen Han left Slate, so I left Slate’s Spoiler Specials and Joanna Robinson left Vanity Fair, so I left Still Watching. Lastly, I stopped listening to MCU Fan Show because there was just too much MCU to justify three-hour-long episodes reacting to every single Disney Plooos installment.

There were also some podcasts that came to an end this year and I was forced to reckon with what a series finale is like for shows that typically aired fifty-two new episodes every year. Magnificent Obsession with Alicia Malone officially hung it up after it seemed quite likely in the fall of 2019. I don’t really understand how Wesley Morris and Jenna Wortham’s Still Processing works, but it seems like it ended this year. The Ringer shuttled off baseball talk to Spotify and wrapped The Ringer MLB Show, which had its fun moments over the years. The Ringer also concluded two more podcasts: Binge Mode (after Jason Concepcion left for Crooked Media and the Marvel series ended, Mallory Rubin’s talents were taken to The Ringer-Verse) and House of Carbs (Joe House might have nothing more to say about food).

Harry Potter and the Sacred Text, once a perennial powerhouse on these lists, bid farewell to dynamite cohost Casper ter Kuile and restarted the books. After five years going chapter by chapter and watching the ending of my favorite book, Deathly Hallows, get squandered by the podcast, though, I decided I wouldn’t venture back through the seven texts with Vanessa Zoltan and Matt Potts. I hope they have their fun.

Sports? with Katie Nolan lost producer Travis Rockhold to Tennessee and then, in a few weeks, lost Katie Nolan herself when she departed ESPN at the end of September. This left the great dynamic of Katie and the Union (Travis and Christina Buswell) one in the past. I’m still sad because we didn’t get a true finale of Sports? It just kind of died. I remain hopeful that Katie Nolan’s podcasting talents will find somewhere else to thrive. I’ll have more to say on this podcast later!

Ask Me Another, once my favorite NPR podcast with no other contenders, also came to an end this year when NPR announced they were cancelling it. It was always a fun podcast with some really game celebrity guests, some genuinely entertaining contestants, and some catchy puzzle songs from Jonathan Coulton. I’ll have more to say about this one later, too, but it definitely had the better podcast series finale when compared to Potter and Nolan. (Through no fault of Nolan’s.)

Talking Sopranos is the last podcast I listened to that came to an end in 2021. Arriving at the series finale, “Made in America,” to discuss with David Chase, the Sopranos rewatch pod hosted by Michael Imperioli and Steve Schirripa had plenty of HBO mob families to talk about this year. In addition to the final season, the pair also broke down The Many Saints of Newark, the prequel film from Chase that bowed this autumn. It was just reassuring to know that rewatch podcasts do eventually get to the series finale, though.

That was a major trend for podcasting in 2021: the rewatch pods from B-tier cast members of all your favorite shows from the past twenty years (or cultural critics reviewing the episodes with the occasional interview). Talking Sopranos obviously came before Office Ladies, but it’s clear that Office Ladies ripped the dam open. Now, we have those Marc Evan Jackson-hosted pods about Brooklyn Nine-Nine and The Good Place (since finished) and official companion podcasts for Late Night with Seth Meyers, Only Murders in the Building (this one made sense), and For All Mankind. Sneha Goud hosts Project Mindy, a Mindy Project re-up, and Hector Navarro & Frankie Grande host SpongeBob BingePants, a cultural reassessment of the best of SpongeBob. Not to mention, Zach Braff and Donald Faison are deep into the fifth season of Scrubs on Fake Doctors, Real Friends. Plus, Glenn Howerton, Rob McElhenney, and Charlie Day host The Always Sunny Podcast, Rob Lowe and Alan Yang host Parks and Recollection, Maggie Lawson and Timothy Omundson host The Psychologists Are In, Scott Patterson hosts I Am All In, Zooey Deschanel, Hannah Simone, and Lamorne Morris host Welcome to Our Show, and Timothy Simons and Matt Walsh host Second in Command. (These are for It’s Always Sunny in Philadelphia, Parks and Recreation, Psych, Gilmore Girls, New Girl, and Veep, respectively.) There are too many! Way too many! I can only keep a few in my feed. I will not say which ones I kept. Can’t wait until Alec Medlock and Scott Halberstadt rewatch Drake & Josh.

Just too many rewatch podcasts! And too many podcasts in general, perhaps. That’s why I culled so many shows. It was unruly! This is all without even getting to the honorable mentions yet.

First, though, I do want to plug the pods of people I know personally. My friend’s work on Goodbye Mello Brick Road and Anatomy of a Trading Card is still worthwhile. Same goes for Film Frauds and Try Again. Bryce and Ren and Ned’s Declassified School Survival Guide just went deep on the Roys and the Grinches. And, of course, Spoilers! remains one of my all-time favorite pods and I love whenever I get to appear on the show to defend Taylor Swift, too.

There were also some podcasts I only listened to one or two episodes from. I want to shoutout those episodes, even if the breadth of the podcast, as a whole, did not stick for me. Christmas 365 covered the Ted Lasso Christmas episode with aplomb. The Friendship Onion played host to lovely reunions between Dominic Monaghan, Billy Boyd, Elijah Wood, and Sean Astin. How Did This Get Made? welcomed back Adam Scott for F9. The Letterboxd Show interviewed Demi Adejuyigbe and Sean Fennessey about their four favorite films. Both Metaphysical Milkshake and The Office Deep Dive had stellar interviews with Michael Schur. The Purple Stuff broke down the Halloween monster cereals. Storytime had a great tale about Paul Rudd, hosted by Seth Rogen. And The Ringer NFL Show conducted an NFL Rewatchables for Super Bowl LI, my favorite football game of all-time. (It’s when the Patriots orchestrated a monster comeback against the Falcons.) These were all lovely installments!

Now, though, for the actual honorable mentions. D23 Inside Disney is the Disney theme park and movie news podcast I always wanted. The Filmcast, Filmspotting, and The Weekly Planet all continue to do solid work on the movie review front. Pop Culture Happy Hour continues to thrive in the daily format. Section 10 pivoted into becoming unexpectedly relevant for this Red Sox season before bidding farewell to cohost Steve Perrault. (Their Dustin Pedroia post-retirement interview was a fantastic one.) Be Our Guest remains a must for all Disney vacation planners. Unofficial Universal Orlando Podcast really came into its own this year, too, as it covered Halloween Horror Nights magnificently. The Mina Kimes Show featuring Lenny taught me more about football than any CBS pre-show ever did. Rolling Stone Music Now usurped Popcast as my go-to for music news and reviews. The Dave Chang Show had a ton of fun toying with the show’s format. And, lastly, some of the best interviews on WTF with Marc Maron included Benedict Cumberbatch, Ridley Scott, George Clooney, Jane Goodall, Julie Delpy, B.J. Novak, Matt Damon, Joseph Gordon-Levitt, and Eddie Murphy.

With all that housekeeping out of the way, here are the podcasts I thought actually represented the best of the medium in 2021!

15. The Rewatchables

Image from Apple

I clamored too long for Bill Simmons to start a movie revisit podcast with his Grantland companions to not include it on the list, but even I can admit that 2021 was a down year for The Rewatchables. I stopped keeping up with every episode if there was a movie I didn’t see and Simmons’ taste really started to gnaw at me. (They seriously covered a Miami Vice television movie this year. Country Strong was way more defensible.) But there were some good movies covered in spite of it all (Halloween, Trainspotting, Superbad, Legally Blonde, Raiders of the Lost Ark, Goodfellas, Neighbors, Coming to America, Out of Sight, The Royal Tenenbaums, Bridesmaids) and some fun guests (Andy Greenwald, Mina Kimes, Bill Lawrence, Bill Hader, Wesley Morris, Chuck Klosterman, Michael Mann, Jimmy Kimmel). The Neighbors episode is a particular standout, to me, because of the lengthy Seth Rogen treatise.

14. Too Long; Didn’t Watch

Image from Apple

My expectations were high at the end of 2020 when Alan Sepinwall began teasing his return to podcasting. Unfortunately, it was not a re-up of TV Avalanche with Brian Grubb, but it was still an endeavor with merit. Too Long; Didn’t Watch has an interesting conceit: a celebrity guest watches the pilot and series finale of a popular show they’ve never seen before. It makes for an interesting analysis and breakdown of shows, especially for celebrities who are also knowledgeable and intuitive television viewers. It would’ve ranked more highly if it didn’t completely disappear from feeds after ten weeks. Some highlights include Jon Hamm watching Gossip Girl, Alison Brie watching Game of Thrones, and Lena Dunham watching Cheers.

13. The Bill Simmons Podcast

Image from Apple

The Bill Simmons Podcast is just a perennial staple at this point. It comes the closest to replicating my experience listening to WEEI and 98.5 The Sports Hub while growing up in New England. I will always value podcasting for emulating that experience on demand. Bill’s 2021 output on the Pod Hub for The Ringer was about the same as it ever was. Ryen Russillo talking NBA, Cousin Sal talking NFL, Jack-O and Dr. Bill talking MLB. But if you throw in his reconnections with stars like Ben Affleck, Matt Damon, Tom Hanks, and Sharon Stone, you get a really well-rounded, competently made podcast.

12. Can’t Wait for Christmas

Image from Apple

A podcast that’s all about Christmas with a host that doesn’t make you dig your fingernails into your steering wheel like Steve Martin in Planes, Trains, and Automobiles can be hard to come by. Fortunately, Tim Babb is an immaculate podcast host, Christmas or otherwise, and his show is a delightful, peppermint-flavored treat when it arrives in the podcasting app every 25th of the month. It’s a monthly dose of Christmas recipes, planning, movies, music, jokes, and more. Not too much, not too spare. It’s the “just right” Christmas podcast and it brings me copious amounts of joy every year.

11. Comedy Bang Bang

Image from Apple

A good year for Comedy Bang Bang can always be determined by how hard it is to vote for the “Best Ofs.” This year, it was practically impossible to narrow the options down! Some of my favorite installments included any appearance of Jon Gabrus as Gino, Neil Campbell as The Timekeeper, Mike Hanford as John Lennon, Dan Lippert as Bill Walton, and Lily Sullivan as anyone. Considering we received all of those in 2021, plus stellar standout turns from stars like Phoebe Bridgers, Andy Samberg, Kelly Marie Tran, Bob Odenkirk, Gillian Jacobs, Manchester Orchestra, and Ben Schwartz, yeah, it was a… rather good year for the pod. Commendable efforts from the production team who balanced Zoom recordings with a return to the studio, too!

10. The Plot Thickens

Image from Apple

If a podcast is only as good as its host, then The Plot Thickens might have an argument for the number one spot. Ben Mankiewicz is easily one of our foremost scholars on film, television, and pop culture history. He treats every subject with reverence and fascinating, no matter how frivolous or perceptively classy, and he does it with a warm, inviting, comforting tone of voice. Mankiewicz is perfect for hosting TCM movies and introducing Fathom events on the big screen, but, as it turns out, he’s also perfect for hosting a TCM podcast. The most recent season of The Plot Thickens covered the entire life and career of Lucille Ball, one of the funniest people to ever exist, and it did so with aplomb. I might even consider the notion that it tops Being the Ricardos! It’s incredibly well-researched, but it also contains a thoughtful narrative on the pioneer, Ball. Well done!

9. The PosCast with Joe Posnanski & Michael Schur

Image from Apple

Another year, another logo. Usually, The PosCast releases episodes sporadically throughout the year and then comes in to secure to a top ten spot on the heels of a remarkable “Holiday Draft” episode. It’s my favorite tradition in all of podcasting and it always vaults The PosCast into the top ten. Five years running now! Joe Posnanski and Michael Schur, however, made the move to Meadowlark Media in 2021. This meant that they had a regular schedule to their episodes with all the thoughtful, accurate baseball talk and meaningless drafts that we’ve come to expect from them both. Dan Le Batard’s venture away from ESPN remains one of the most exciting developments (Le Batard & Friends is a good pod, too) and adding Posnanski and Schur to that umbrella is a big reason why. But, of course, they also drafted Holiday Objects in December and the cornucopia breakdown lives in the annals of PosCast lore. This year’s event included Posnanski, Schur, Alan Sepinwall, Linda Holmes, Brandon McCarthy, Mike DiCenzo, Nick Offerman, Jason Kander, Ellen Adair, and newcomer Alexis Gay, who fit in perfectly. It’s delightful and giddy and always a highlight of the year. I highly recommend listening to them!

8. Ask Me Another

Image from Apple

As I mentioned above, Ask Me Another came to an end this year. It was always such a fun game show in a podcasting format and you could tell that a lot of intellectual thought was put into the puzzles, games, and clues. Ophira Eisenberg was a hilarious host who was perfectly suited to the pod and Jonathan Coulton has a really gorgeous singing voice. I’m glad they kept up the quality output, even when NPR announced that they were cancelled. The series finale was one of the best episodes of the year, too. They blended highlight clips from Ask Me Anothers past and brought in beloved, fan-favorite guests for one last spin around the anagram machine. Myosis! (Miss you.)

7. Tea Time

Image from Apple

Last year’s runner-up did fall a few spots this year, but it still remains one of my favorite podcasts to listen to. There were just a lot of new gems in 2021! But Tea Time, from hosts Kate Halliwell, Liz Kelly, and Amelia Wedemeyer and producer Kaya McMullen, is one of the most entertaining roundtable podcasts we have and a tremendous cultural conversation from the Ringer Dish feed. Between Mamma Mia! on “Cringe Mode,” the latest Taylor Swift updates, a breakdown of Spotify Wrapped, and a reckoning with Paul Rudd as People’s Sexiest Man Alive, it was yet another stellar year in the culture that really matters. Don’t get bogged down in Adam McKay discourse. Just enjoy the truth that Tea Time provides.

6. The Big Picture

Image from Apple

The past two years of The Big Picture have kind of started to blend together as new movie releases have only just become consistent again, rather than sporadic. But it doesn’t matter because the Sean Fennessey/Amanda Dobbins/Chris Ryan-hosted and Bobby Wagner-produced podcast has been stellar throughout the pandemic. They still make room for the odd, theatrical pearl on The Big Picture, but there has also been a deluge of Movie Drafts, Movie Auctions, All-Time Lists, and an interlude miniseries for a Gene and Roger (Siskel and Ebert, that is) docu-pod while Fennessey had his first child. That’s an immaculate year for any podcast; it just so happens that The Big Picture was unstoppable, episode-in and episode-out. A Holiday Movie Draft? Something I screenshotted and posted on my Instagram story. A Movie Auction that results in Chris Ryan having four Marvel movies? A lovely memory of walking around the block. Plus, Fennessey got to host breakdowns for so many acclaimed directors. Steven Spielberg, Wes Anderson, Jane Campion, Paul Thomas Anderson! 2021 was an improved year for movies (we bounced back!) and a great year for those who covered them.

5. The WDW Radio Show

Image from Apple

I’m not sure how I should proceed with including WDW Radio on the list. It’s like the Bill Belichick of podcasting. If we’re being honest, Belichick should be Coach of the Year every year in the NFL because what he’s doing is so unprecedented and unlikely to ever be replicated. That’s how I feel about Lou Mongello and WDW Radio. It’s so obviously immaculate that it almost feels too easy to put it at number one, even though it deserves it. However, I met Lou Mongello this year and am working up the nerve to meet him again, so if I don’t include Spoilers! on the list because it’s unfair to those I don’t know, maybe that might be the future of WDW Radio. For now, I just want to celebrate another special year for the podcast. It remains the greatest travel and theme park podcast of all-time and Mongello’s touch as a host is unrivaled. Trip reports to every Epcot festival, an entire series on the presence of music in each park, continued live dining and resort report shows, lists with Little Timmy Foster, and an interview with Mike Brassell, the voice of the PeopleMover? I mean, come on. If you’re a Disney nerd, that previous sentence must sound like heaven.

4. The Watch

Image from Apple

Last year’s number one podcast is at number four this year, but it’s not because of any drop in quality from Chris Ryan, Andy Greenwald, or Kaya McMullen. The Watch is as stellar and as highly-anticipated by me as it ever was. Again, there were just some really awesome shows I discovered this year. Anyway, The Watch is incredible because I find myself drawn to the same aspects of culture that they are. I, too, am enthralled by Bluey, fascinated by the streaming wars, and curious about everything Marvel tried to do this year. But the only thing better than the chemistry of two fun friends unpacking their weekend experiences or latest mystery recipes is when they find a show they vibe with and we roll with episode recaps and reviews for a couple weeks. Succession, The White Lotus, Loki. It was a great year for television reviews from two of the best to ever do it!

3. Every Single Album

Image from Apple

I know a lot of people listen to Every Single Album and I know Nora Princiotti and Nathan Hubbard host and curate it. But it really feels like their December 22 episode, “‘The Taylor Swift Holiday Collection,’” was created just for me. I mean, it had a discussion on Christmas music, including more modern staples like Michael Buble’s “Christmas (Baby Please Come Home),” (my favorite holiday song ever) and Jonas Brothers’ “Like It’s Christmas.” But beyond that it broke down the entire Taylor Swift holiday oeuvre, from her 2007 holiday LP to the merry versions of “Christmas Tree Farm” to a consideration of Evermore as a holiday album, courtesy of songs like “‘Tis the Damn Season,” which might be my favorite T-Swift song (I don’t know; it changes a lot). That episode was just everything I could have possibly wanted from a podcast that was already doing incredible work throughout the year. Princiotti and Hubbard broke down every Taylor Swift album ever with fun drafts, fun categories, and fun discussions on music we all adore. But then they went further by analyzing Sour by Olivia Rodrigo and every Adele album! For music nerds who love their unabashed pop stars, Every Single Album is the way to go.

2. Sports? with Katie Nolan

Image from Apple

We hardly knew ye. I’ve loved Katie Nolan for years, but only started listening to her podcast in full in 2021. Oh my goodness. I’ve been missing out all these years! I never jumped in the KAJ, but I really enjoyed the chemistry Nolan had with Travis Rockhold and Christina Buswell, who comprised the Union. I fell in love with Sports? during Third Month Crazy Time when there were brackets about appetizers, places to have a drink, NFL on television theme music. March for Sports? was one of the best months any podcasts has ever had. But as the year went on, I found myself going to Sports? first in my feed on Tuesdays and Thursdays. I was delighted to see new episodes come in because I knew they promised nuanced conversations on sports, the trio’s opinions and lives, and updates on mental health. It became so much more than a sports podcast; it’s no wonder ESPN didn’t know how to hang onto what they had. Long live it!

1. Blank Check with Griffin & David

Image from Apple

Don’t know what to say or to expect! All you need to know is that the name of the show is Blank Check! That’s how the theme song goes. But it’s a pretty accurate descriptor of the show, too. I think, sometimes, I’m bad at explaining what the podcasts are actually about because I’m so accustomed to them that I speak about them in shorthand. (To clarify, WDW Radio is a podcast all about the Disney theme parks and, occasionally, the Disney world, writ large.) Blank Check is a movie review podcast, yes, but not your average one. Blank Check goes through director filmographies one week and one movie at a time. This allows them to provide context to a director who factors in on film history, from the actors they work with to the “blank checks” they receive, and what happens when those checks cash or when they bounce. It’s a profoundly engaging way to think about movies and the only new releases they cover are when a director they previously spoke about releases a new movie (this year, Steven Spielberg made West Side Story and M. Night Shyamalan made Old, for example) or when producer Ben Hosley (an incredible podcast presence) makes his own choice. It’s hosted by Griffin Newman, a comedian and actor from Draft Day, and David Sims, a critic for The Atlantic, and they provide just as much humor as they do film nerdiness and a love for the medium. A friend has recommended the show for years and I got into them fully and wholeheartedly in 2021 when I learned they do annual March Madness tournaments to determine a filmmaker they’ll cover and their own Oscars with Joe Reid. It’s everything I love to do myself, already! Their miniseries this year included the tail-end of Robert Zemeckis, Ron Clements and John Musker (my favorite miniseries they’ve ever done and, yes, I went back through them all), Elaine May, Joseph Gordon-Levitt, John Singleton, and John Carpenter. (2022 begins with Jane Campion.) I’m still rooting for Gore Verbinski, but that’s an impeccable batch of filmmakers all the same. It’s a great honor to be a Blankie in 2021.

What will 2022 bring for podcasting? Well, if you actually read these, I’m sure you’ve grown accustomed to seeing some familiar names on the lists every year. Sean Fennessey, Amelia Wedemeyer, Lou Mongello. They’re all likely to pop up again here next year. But maybe Adam Scott Aukerman will reform for another musical group coverage series. Maybe The Ringer will release the greatest podcast of all-time. Or maybe they’ll be something new from someone new that we never could’ve predicted. It’s the Industrial Revolution of podcasting and I can’t wait to see what goes up.

More from the Best of 2021 series:

The Best of 2021: Tweets

The Best of 2021: Books

See also:

My 20 Favorite Podcasts of 2017

(#1 was The PosCast)

My 15 Favorite Podcasts of 2018

(#1 was R U Talkin’ R.E.M. Re: Me?)

My 20 Favorite Podcasts of 2019

(#1 was You Made It Weird with Pete Holmes)

My 20 Favorite Podcasts of 2020

(#1 was The Watch)

--

--

Dave Wheelroute
Saoirse Ronan Deserves an Oscar

Writer of Saoirse Ronan Deserves an Oscar & The Television Project: 100 Favorite Shows. I also wrote a book entitled Paradigms as a Second Language!