My 20 Favorite Podcast Episodes of 2019
Who can it be now?
I’ve written so much about podcasts here. But I love to do it. I hope you’ll humor me with one more list on the matter. At least, until 2021 rolls around, of course. But yes, podcasting. One of my favorite mediums! Nothing makes me feel more at home than a fun, familiar podcast.
And there were so many great ones that I just wasn’t able to find room for! Pop Culture Happy Hour had a ton of great episodes this year. My personal favorite was when they covered Doctor Sleep. Marc Maron interviewed Stephen Colbert over on WTF. Marvel Studios News did an entire “In the Endgame” series leading up to the release of Avengers: Endgame, which each episode featuring a different Marvel character profile. The /Filmcast interviewed Rian Johnson about Knives Out and knocked the annual Summer Movie Wager out of the park again. Filmspotting hosted “Filmspotting Madness” once again. And the team behind the Unofficial Universal Orlando Podcast finally visited the parks in their “Weekenders” series.
It was really an amazing year for podcasts! My own podcast, Goodbye Mello Brick Road, also had some absolute peaches of episodes. And Mugglecast had an episode that featured a dear friend of mine!
But since I just covered the “Decade in Podcasts,” I figured to do another Best Podcasts countdown would be tiresome. Therefore, I decided to change it up with the year’s best podcast episodes. Ah, yes. Clever, clever.
And without further ado, here are the twenty best!
20. The Weekly Planet: Comic Con 2019 & Wooo
It’s hard to pick a specific episode from The Weekly Planet because of how consistently funny they are. But I enjoyed this one because of their crack-up diatribe about what the character of Moon Knight gets up to in the comics and how he could translate to the Disney Plooos screen. Besides, what better episode for a comic book movie news podcast could there be than the Comic Con recap one?
19. Modern Love: “Let’s Meet Again in Five Years” with Regina King
Modern Love had a big year when it was adapted for the small screen. Still, though, the podcast managed to produce some great episodes. My favorite was the one narrated by Regina King. It told the story of people who agreed to see if they might pursue a further relationship at the exact same spot five years in the future. There’s tons of twists and turns packed into the twenty minute run time!
18. Can’t Wait for Christmas: National Lampoon’s Christmas Vacation
2019 marked a transition for my Christmas podcast listening. While The Christmas Stocking withers, Can’t Wait for Christmas rose up in its place. It’s a low-commitment, high-enjoyment podcast that is purely wholesome. My favorite episode produced by Tim Babb was the show’s celebration of the thirtieth anniversary of Christmas Vacation, a hilarious holiday staple.
17. The Empire Podcast: Kevin Feige Live Avengers: Endgame Spoiler Special
The Empire Podcast is no stranger to spoiler specials. But when Avengers: Endgame came out, every week seemed to bring a new spoiler special about the movie. There were so many that I’m surprised Chris Hewitt and Helen O’Hara didn’t team up for an All-Portals Scene Spoiler Special. (I won’t rule it out.) That being said, my personal favorite was when Kevin Feige was brought into the fold to conduct a postmortem in the wake of the film’s release. He had such great insight. Empire continues to have astounding access to filmmakers and movie stars.
16. WDW Radio: Finding Florida
Whether he’s ranking his favorite things about various Disney parks elements, interviewing the movers and shakers of the company, or doing live food reviews, Lou Mongello is always vastly engaging throughout episodes of WDW Radio. But the two-part “Finding Florida” episode is a compelling, heartwarming bit of narrative form from Mongello. He crushes it, as he does with everything.
15. Comedy Bang! Bang!: 2019 Holiday Spectacular
These lists can probably just have a permanent spot open for the Comedy Bang! Bang! and their holiday spectaculars. All the fan favorites come to hang out together and it results in a cacophony of comedy. In the past, the holiday spectacular has featured Leo Karpatze and the Time Keeper, among others. This year, it seemed like Gino was given the reigns for the ep. What could be better than that?
14. Magnificent Obsession: Natasha Braier
Magnificent Obsession is a beautiful passion project podcast from Alicia Malone. One of the newest TCM hosts, Malone has an infectious love and a deft knowledge about the medium of film. It comes through in her show distinctly and always in a way that teaches the listeners something they never would have known before. Her interview with Natasha Braier, the cinematographer for Honey Boy, was extremely thoughtful and just made for a great, wintry listen!
13. Binge Mode: Harry Potter — The Farewell
2019 has seen episodes of Binge Mode that tackled Harry Potter, Game of Thrones, and Star Wars. I love everything they do, but the Harry Potter saga was my favorite tenure throughout Binge Mode’s run so far. Chapters for the end run of The Deathly Hallows were incredible, but “The Farewell,” the entire wrap-up of the season was just beautiful. A testament to why we return to these stories again and again. Mallory Rubin and Jason Concepcion are doing amazing work!
12. Quentin Tarantino’s Feature Presentation: Quentin, You’ll Be a Director Soon
Ahead of the release of Quentin Tarantino’s latest film, Once Upon a Time in Hollywood, The Ringer and Amy Nicholson teamed up to release Quentin Tarantino’s Feature Presentation, a podcast miniseries about the creative anatomy of one of the world’s biggest filmmakers. This particular episode was the conclusion of the show’s run and it made for a perfect companion piece with the actual film itself.
11. The Big Picture: The Tom Hanks Hall of Fame
I think The Big Picture is the podcast I get the most excited to see a new episode from in my feed. There is always a delightful conversation to be had. Whether it’s Sean Fennessey and Amanda Dobbins discussing the Oscar race or the latest theatrical release or Fennessey interviewing a big time director, I listen to nearly all segments! This year, Fennessey interviewed great filmmakers like Jordan Peele and Greta Gerwig, devoted a ton of time to the aforementioned Once Upon a Time in Hollywood, and hosted “Marvel Month” ahead of the release of Avengers: Endgame. But my favorite episode was the first “Hall of Fame” they ever did in The Big Picture. It was a super fun format wherein every Tom Hanks movie was nominated for the “Hanks Hall” and Fennessey and Dobbins worked to select just ten for induction. I love movies!
10. R U Talkin’ R.E.M. Re: Me?: Mike Mills Talkin’ R.E.M.
R U Talkin’ R.E.M. Re: Me? was not as prolific as it was last year (how could it be?), but the team of Adam Scott Aukerman still managed to put out some stone cold quality #content! My favorite of the batch was definitely an interview conducted with Mike Mills, from the actual band, R.E.M., wherein he is clearly in on the joke and having fun.
9. Book of Basketball 2.0: Steve Kerr on 25 Years with the Secret
Bill Simmons’ Book of Basketball is one of the defining pieces of sports literature. To follow it up after an immense wave of changes to the sport over the past decade, Simmons decided to tackle the book in podcast form. He’s revisited players and rewatched iconic games with preeminent NBA experts. But the best episode of the new limited series came when he interviewed Steve Kerr, the former Chicago Bull and current coach of the Golden State Warriors. Perhaps no basketball mind was better to kick the show off with than Kerr’s.
8. This Is Branchburg: Everybody Wants to See My Teeth
The absurdist humor of This Is Branchburg is perfect, especially if you ride for Brendan O’Hare, Cory Snearowski, and their original sense of humor. But the idea of using a local radio station as the format for a comedy podcast is such a cool idea to me. This episode is exactly what you think it would be about. A man runs around town, proclaiming that everybody wants to see his teeth. Listen and enjoy.
7. Office Ladies: “Health Care” with Rainn Wilson
Office Ladies is far and away the best new podcast of 2019. Jenna Fischer (Pam Beesly) and Angela Kinsey (Angela Martin) are currently in the midst of recapping every episode of The Office with genuinely interesting behind-the-scenes stories and fast facts that could only come from people who worked on the show. The best part? More Office alums come by! David Koechner (Todd Packer) and Paul Feig (director) have helped Fischer and Kinsey out. Creed Bratton (Creed Bratton) is due for an episode soon. And Rainn Wilson (Dwight Schrute) provided the best turn of all, bringing infectious joy, love, and enthusiasm when reminiscing about the season one episode, “Health Care.”
6. The Director’s Cut: Once Upon a Time in Hollywood with Quentin Tarantino and Paul Thomas Anderson
It’s amazing how much content is provided to us by The Director’s Cut. I don’t even really get how they do it! But every week, a flurry of episodes are dumped in the feeds about great new movies. They’re not just reviews of the latest films, though. They’re interviews with the directors, conducted by other directors. Paul Thomas Anderson gushing over Once Upon a Time in Hollywood with Tarantino was my favorite, but there’s literally so much to savor here.
5. The Watch: The Top 10 TV Shows of the Decade
The Watch has always been a loyal companion over the past couple years of my life. Andy Greenwald and Chris Ryan almost feel like friends of mine when they’re talking about The Mandalorian, Watchmen, Game of Thrones, Succession, Fosse/Verdon, and Fleabag and visiting the set of Briarpatch. But my favorite episode came in right under the wire this year. Sam Esmail (the creator of Mr. Robot) and Kaya McMullen (the podcast’s producer) joined the hosts to count down their ten favorite television shows of the decade. It plastered such a smile on my face. I have so much respect for Ryan for putting Thrones at number one, too.
4. The Rewatchables: The Shining
The Rewatchables released so many fantastic episodes this year. Happy Gilmore with the Safdie Brothers, Butch Cassidy and the Sundance Kid with Aaron Sorkin, Dunkirk with Tarantino, No Country for Old Men with Bill Hader. The Forgetting Sarah Marshall and Top Gun episodes were also such gems. But on Halloween, Bill Simmons, Sean Fennessey, and Chris Ryan gushed about The Shining and it made for spooky, atmospheric listening. A perfect movie to receive the rewatchable treatment.
3. The Bill Simmons Podcast: Matt Damon Returns
Last year, the Matt Damon episode of The Bill Simmons Podcast was an undeniable highlight. I appreciated it as something that would likely be a once-in-a-podcast event. But not quite! Apparently, Damon enjoyed himself because he came back for an episode that topped the first installment. From stories about David Fincher to stories about the Staples Center, Damon can hang with the best of them. He is so good at being a podcast guest. And Simmons is a great host! It was hard to narrow down just one episode from a great year for Simmons that featured classic “Guess the Lines” segments with Cousin Sal (as well as the Super Bowl Prop Bets pod), “Throne Game” breakdowns with Ryen Rusillo, intellectual guest turns from Chuck Klosterman, interviews with John Skipper, Ben Stiller, Adam Sandler, and Kevin Garnett, and an all-time 500th episode of the show that will go down in the history of Simmons lore.
2. The Poscast: 3rd Annual Holiday Draft
Just as there is always a spot on this list reserved for Comedy Bang! Bang! and their holiday spectaculars, so too has The Poscast carved out a niche with the holiday drafts. In year one, The Poscast crew of Joe Posnanski, Michael Schur Linda Holmes, Alan Sepinwall, Brandon McCarthy, and Mike DiCenzo drafted holiday songs. In year two, they added Nick Offerman to draft holiday characters. In year three, they added Megan Amram and drafted holiday foods. It just gets better and better. It might just be my new favorite tradition! Not only was this year’s episode just as hilarious and enchanting, but it was also for charity. A good cause and a good time; what’s better than that?
1. You Made It Weird with Pete Holmes: Demi Adejuyigbe / Colin Hay
The answer is this! Only one podcast topped The Poscast this year. And I just couldn’t narrow down the episodes! Pete Holmes is a comedian who has grown on me gradually over time. But in 2019, he finally broke through for me when I discovered his stellar interview podcast. The Demi Adejuyigbe (The Good Place) and Colin Hay (Men at Work) episodes were my favorites for sure. I listened to Demi’s episode while on an LAX flight to Australia and I listened to Hay’s episode on a fun little Wednesday afternoon. Not only are they both extremely funny, but Holmes’ insistence on discussing philosophy and religion also leads to thought-provoking, edifying, and moving discussions. I treasure these two interviews and I’ve listened to them for wisdom and joy. That’s what podcasting is all about. Thank you, Pete Holmes.
See also:
My 11 Favorite Podcasts of 2016
(#1 was Modern Love)
My 20 Favorite Podcast Episodes of 2017
(#1 was The Poscast)
My 15 Favorite Podcasts of 2018
(#1 was R U Talkin’ R.E.M. Re: Me?)
My 35 Favorite Podcasts of the Decade
(#1 was U Talkin’ U2 to Me?)
More from the Year in Review:
