My podcast choices lean toward entertainment, pop culture commentary, sports, and the business of technology. I update this list from time to time.
My listening habits fall into a couple of broad categories.
The Dan Le Batard Show with Stugotz – I’ve been listening to this radio show (which is also available as a podcast) for years. It embraces the absurdity of sports while also appreciating sports. And in-between the nonsense they often discuss race and other important topics. I find the occasional conversations with John Amaechi to always be enlightening–Amaechi is one of the most thoughtful and impressive thinkers I’ve encountered. This show expanded my worldview and my empathy. Not bad for a silly show that makes fun of sports.
Blank Check and Blank Check Special Features (via Patreon) – It took me a while to warm up to this movie podcast, but hosts Griffin Newman and David Sims won me over with their unabashed enthusiasm. They really like movies. They really like talking about movies. They really like talking about movies together. They also take their time with each film they review–episodes often go longer than two hours–and the extra space works well. They go on tangents. They make callbacks. They do bits. They also have the most creative ads I’ve heard (I look forward to the ad reads).
Judge John Hodgman – This show has a great hook: people bickering over something mundane (the more mundane, the better) take their argument to “fake Internet judge” John Hodgman. He asks questions and makes gentle fun of the guests–never going too far–then he renders a verdict. And the verdicts are often quite thoughtful and empathetic. Hodgman’s camaraderie with “bailiff” Jesse Thorn is fantastic, too. I turn to this show whenever I need a break from the pace and noise of daily life. It’s a kind and welcome distraction.
Conan O’Brien Needs a Friend – Conan O’Brien on his own would be insufferable. He’s funny and quick, no doubt about that, but he also slips into bizarre characters and wacky voices that can wear thin. This show works because co-hosts Sona Movsesian and Matt Gourley keep O’Brien in check–they straight-out mock him and he understands their mockery is the key to the show’s success.
The Connect – I’ll listen to anything with Shea Serrano (his movie book is phenomenal as well). In each episode, he and Jason Concepcion look at two movies that are connected in some not-always-obvious way. Examples: “World War Z” and “La Bamba” are movies you shouldn’t watch on a plane; “Juice” and “Out of Sight” both have characters that can’t help making bad decisions; “Ex Machina” and “Upgrade” each highlight the perils of artificial intelligence. It’s a clever idea for a show and the co-hosts have good energy.
Stop Podcasting Yourself – I started listening to this show because the title cracks me up. Turns out, the show is good too. Co-hosts Graham Clark and Dave Shumka run a very casual podcast, but they’re both funny and they often have funny guests, so the laid-back approach works because everyone is cracking up.
Binge Mode – I listened to Binge Mode’s “Harry Potter” series in parallel with reading the books and my experience was heightened. The “Star Wars” series was amazing, and the episode focusing on John Williams and the music of “Star Wars” is the best single podcast I’ve heard.
The Watch – I tend to only listen to this show when they’re discussing a movie or TV show that connects with me. Andy Greenwald can be a bit much sometimes, but there’s no denying that he and Chris Ryan know their stuff. They put a lot of thought into the intersection of culture and content.
Who? Weekly – I liked co-hosts Bobby Finger and Lindsey Weber when they appeared on “Blank Check,” so I started listening to their podcast. I’m a sucker for celebrity gossip. It’s just so stupid. Some see it as the decline of civilization, but I believe any society that can waste time on celebrity “news” must have decent positioning on the hierarchy of needs.
Slow Burn – I was a weird kid who was super interested in Watergate history. Watergate happened years before I was born, but for some reason the whole affair enthralled me. I loved “All the President’s Men” so much as a tween–and it’s still one of my favorite movies. When “Slow Burn” focused on Watergate in its first season, it was as though the nexus of podcasting and my interests finally combined into the perfect form. Subsequent “Slow Burn” seasons investigating the Clinton Impeachment, the Biggie and Tupac murders, and the rise of David Duke are also fascinating.
Land of the Giants – This podcast looks at the success behind today’s mega-companies. Season one focused on Amazon. Season two took on Netflix. These are fascinating explorations. Also, co-host Peter Kafka has a tremendous podcast presence–he’s informed yet casual and he doesn’t use that odd cadence some “newsy” hosts employ.
The Dream – Season one deconstructed multi-level marketing schemes (they’re horrible and predatory and you must avoid them at all costs). Season two cast a critical eye at the wellness industry and its considerable shenanigans.
Spectacular Failures – This is schadenfreude in podcast form. Host Lauren Ober looks at the rise and spectacular (and sometimes kind of delightful) falls of companies like Toys R Us, Kodak, and MoviePass.
Higher Learning with Van Lathan and Rachel Lindsay – Co-hosts Van Lathan and Rachel Lindsay look at the big topics in Black culture. They’re insightful, smart, and funny.
The Bill Simmons Podcast – This used to be one of my go-to podcasts, but now I hold off until Simmons interviews someone interesting.
How Did This Get Made? – Paul Scheer, June Diane Raphael, and Jason Mantzoukas watch absurd movies and offer their thoughts. Really, the movies are just an entry point for their improv.
The Big Picture – I’ll check in on this movie podcast when they’re discussing a film, director, or a movie-related topic that piques my curiosity.
Office Ladies – Jenna Fischer and Angela Martin go through every episode of “The Office” and loop in co-stars and crew to offer behind-the-scenes details. (This podcast is fun, but what I’m really waiting for is the the “Parks and Recreation” re-watch.)
Fake Doctors, Real Friends – Zach Braff and Donald Faison break down every episode of “Scrubs.” Episodes with “Scrubs” creator Bill Lawrence drops are highlights. It’s also got the best podcast theme out there (“5, 6, 7, 8!").
30 for 30 – The “30 for 30” documentary series on ESPN carries over its quality and insight to its podcast. I’m fascinated by re-examinations of historical events from years–sometimes decades–later. The clear-eyed perspective that time creates is illuminating, and it serves as a welcome contrast to the in-the-moment hot takes that make sports discussions so tedious.
Last Seen – This is a limited series from WBUR and the Boston Globe that digs in to the still unsolved Gardner Museum art heist. I was 15 when this heist occurred and I’d recently gone to the Gardner on a school field trip. The museum left quite an impression on me with its unusual layout, its density (art is everywhere in this place), and its beauty. This in-depth podcast looks at the various victims and suspects surrounding the heist.
Off Camera with Sam Jones – I can only take this podcast in small doses. Host Sam Jones lands impressive guests–and that’s the draw–but the interviews are so earnest it can get to be a bit much. Also, the introductory sections are long and duplicative. But beyond that, it’s sometimes a good listen.
Oh, Hello: The P’dcast – John Mulaney and Nick Kroll play George St. Geegland and Gil Faizon, two elderly friends with a lot of relationship baggage who launch a podcast (a “p’dcast” in their parlance) to investigate the death of Princess Diana. It’s bizarre, but I find Mulaney hilarious.