AUTHOR'S NOTE: Some of you may know that I write two (mostly-) weekly blogs, one for my software development firm in my day job and another for my music interests. Keeping up with ever-looming deadlines and a content pipeline to fill is not always easy. Every once in a while, I find a topic like this week where I can write one article that fits in on both blogs.
Not only that, this is long enough to be a 2-parter on 2 different blogs. After I finish this one, I'm putting my feet up for a while.
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If you're anything like me, then first of all, you have my sympathies. But if you're anything like me, you listen to a lot of podcasts. I'm always looking for more great conversations to plug into while walking the dog, driving or all sorts of times. In case you were in the market for some suggestions, I'm making a list of ones you might like.
Instead of recommending whole podcasts series, in this article I'm highlighting and linking individual podcast episodes. Of course, if they're here in this list then it's also an implicit endorsement of that whole podcast so maybe go ahead and subscribe to them if you like it. You know what to do.
I'm breaking this down into a few categories: Humor (probably most of what I listen to), Technology & Business (since it's my job), Music, Film & TV (since it's what I live and breathe most), Sports and then General Interest.
Also, I’m not linking this podcasts directly because I don’t know where you like to listen to yours or what app you use. I’m sure you can take it from here if these interest you.
Strike Force Five - Strike Force Wives
If you're asking what individual podcast have I listened to most, it's this episode and it's not even close. During the writer's strike of 2023, the five preeminent late-night hosts, Jimmy Kimmel, Stephen Colbert, Jimmy Fallon, Seth Meyers and John Oliver all banded together with a podcast to raise money to pay their staffs. Though competitors, these guys are all close, had a Zoom going on with each other that they took public and they just happen to be five of the most professionally funny people in entertainment. Then on this particular episode, add Jimmy Fallon's inability to ask a straight question in trying to run a version of The Newlywed Game and the other four mercilessly making fun of Fallon makes for podcast gold. You might already be a fan of the dynamic on Smartless where Bateman, Arnett and Hayes make fun of each other. But this is 10x better. I. Can. Not. Recommend. This. Enough.
The Bill Simmons Podcast - Adam Carolla
I think if you're a fan of podcasts then you don't need me telling you about this podcast. There are so many great episodes and I could have fit certain episodes into the categories of sports, film, whatever. I started listening to podcasts around 2007 where WTF and the BS Podcast stood out early. And this installment with Adam Carolla pitching his fake movie, "Pedof Isle" is the hardest I've ever laughed while wearing headphones. I miss when Adam Carolla liked talking with other smart interesting people instead of yes-men.
You Made It Weird - Garry Shandling
On Pete Holmes podcast he goes deep with guests while keeping it light and I love about 80% of his sensibility. I do need to confess: in this article I could highlight 5+ Marc Maron episodes and 3+ Gilbert Gottfried episodes; and here I could easily be recommending the Garry Shandling episode of WTF. That aside, Shandling is an incredible blend of emotional depth and sharp comedy. The WTF episode with him was about 100 minutes and the YMIW one here with Pete Holmes was about 140 minutes so it wins. Do it up.
Family Trips With The Meyers Brothers - John Mulaney
First of all, I'm totally in the bag for Seth Meyers. There might be funnier guys in comedy (not many) but he is the perfect host and foil / sounding board for other funny people. The other factor here is that I could listen to John Mulaney talk to anybody about anything at any time. So, when you put Seth Meyers and John Mulaney together, I'm absolutely sold. If you get into this, then jump onto the John Oliver episode next.
The Ron Burgundy Podcast - Theme Song
I could have used this space to recommend an episode of Smartless but you already know about those guys. Instead, I need to ask: have you heard Will Ferrell's Ron Burgundy Podcast? You know Will Ferrell. You know Anchorman. But please make sure you've tried this podcast. All of the improv over-the-top insanity you expect is here. And I'm just smiling right now thinking about the Doris Kearns Goodwin ep and the Ru Paul one. Yet, you need to start with this one from Season 1 recording the Ron Burgundy Podcast theme song. "Take Back The Night!"
Norm Macdonald Live - Bob Einstein
I feel a little bad about recommending this since I can't find episodes currently showing in my iPhone's podcast app. But Norm was the funniest and smartest fucker I've ever heard. So, you might have to seek some of these out on YouTube or god knows where. Now, if there's anybody on earth who's made me laugh out loud as much as Norm Macdonald it might be Bob Einstein. Super Dave's appearance on Norm's show and being hilariously outraged at Norm slumming on a low-rent podcast is constantly funny. This is pull-your-car-over-to-the-side-of-the-road-so-you-don't-get-hurt-while-laughting funny. A close runner up is Bob Einstein on Gilbert Gottfried's podcast.
The Ricky Gervais Show - Season 1, Episode 7
For a while, I know this was the most downloaded podcast of all time. When listening to podcasts, in a very weird and intimate way, these guys become your friends. And your friends ragging on each other can be hilarious. My #1 choice for that is the aforementioned Strike Force Five episode. And we get the vibe of Smartless. But even Smartless takes a back seat for me compared to Ricky Gervais and Stephen Merchant grilling the fucking insane Karl Pilkington on this podcast. Jesus.
Runners-Up: Conan O'Brien Needs A Friend - Stephen Colbert. Almost anything from Paul F. Tompkins or Jimmy Pardo. The Drifting Off With Joe Pera podcast.
And I do want to make sure you've subscribed to Neil Brennnan's "Blocks" podcast.
Technology & Business
Similar to current events and politics podcasts, tech ones can get instantly dated. But here are some individual episodes I definitely remember.
Freakonomics - Why Are There So Many Bad Bosses?
These guys are the best week-in and week-out for deep dives into interesting topics. I chose this episode because there is nothing more vexing than dummies in relative positions of power. And they do a great job of almost explaining why The Peter Principle is the way of the world. Almost.
Daniel and Jorge Explain the Universe - What Does Artificial Intelligence Mean?
A.I. is going to continue to be the most important issue out there for all of us, at least professionally. It's an incredibly wide-ranging topic - this great discussion takes a broad swipe at defining A.I. and is equally insightful for novices and experts. Even in the 4 years since this podcast, the term AI has already shiften a lot; but this is still the best primer I can think of when it comes to Artificial Intelligence.
This American Life - 129 Cars
Yup, This American Life is one of the godfathers of the podcast world. And usually while it's an exercise in storytelling more than business advice, this one about making sales at car dealerships is pretty wonderful.
How I Built This - Ben & Jerry
Enterpreneurial advice from business successfully usually comes with an intolerable amount of ego. But host Guy Raz is pretty level-headed and then this episode features the always affable Ben & Jerry. Worth a listen.
The Bill Simmons Podcast - Jack Dorsey
Sometimes the BS podcast dips its toes into the business world. Prior to this, I'd never hear the Twitter CEO speak. I was shocked at how sensible and human Dorsey was. Which is shocking, considering the track record of other barely-human tech CEOs.
Before recommending specific great individual shows, I should tip my cap to some music critics using the podcast format to patrol their beat. I've been critical of rock critics previously. But NPR's All Songs Considered and also The Sound Of Success Of Nic Harcourt makes one believe that great rock criticism didn't die with Lester Bangs and Greil Marcus. And you probably know Song Exploder which IMHO is good, not great - all falls short of the idea of "director's commentary" for music.
WTF With Marc Maron - Wayne Coyne
Lets face it, there's probably no more enjoyable and wide-appeal podcasts than WTF and The Bill Simmons Podcast. I could have included one of each in just about each category here of these lists. Anyway, for music I'm opting for this great talk with The Flaming Lips frontman. I needed this one in the pandemic era and they both processed the loss of loved ones. And it's also a fascinating 90 minutes as you hear two people become friends in real time. Anyway, take your pick of WTF episodes. You already know it but I wanted to steer you to this one. Runner up for WTF: The best Randy Newman interview I've ever heard, and I say that as somebody who idolizes Randy.
Reply All - The Case of the Missing Hit
I really should have included a Reply All episode in the tech section. Their one about QAnon is a classic - and the banality of the Qanon evil. But this one about how an actual hit song could actually disappear is really amazing and something to behold.
The Tim Ferriss Show Presents - Derek Silvers
More than other podcast fans, I can take or leave the Tim Ferriss show to an extent. I appreciate what he does in theory, but I can get a little bored - even on an episode as insightful as Tony Robbins on Achievement vs Fulfillment. That said, his guest on this episode with Derek Sivers is incredible. Derek's ethos and achievement of CD Baby for indie artist to distribute their music. A fascinating CEO in that his end goal was not rooted in maximizing profits; making some money but doing right by your customers was and is admirable. A great listen.
Cocaine & Rhinestones - Stand By Your Man: The Anti-Feminist Manifesto
Kind of reminds me of Mike Judge's animated documentary series Tales From The Tour bus about the wildest stories about the wildest stars in county music (PLEASE watch that). I just love this guy's tones - it's like autistic AI audio with snark finding meaning in pop culture.