Over the past couple of days I've been trying to listen to every single podcast episode that Ezra Klein and Ta-Nehisi Coates have recorded together. They're both brilliant, obviously, but what appeals to me most about their podcasts is how they have fantastic and really complementary conversational chemistry. And even when they're talking about super-serious, kind of dark stuff, they can be really funny, like laugh-out-loud-to-myself-on-the-treadmill-while-running funny.
Other people I've gotten kind of obsessed with listening to: Dr. Peter Attia, Malcolm Gladwell (on certain podcasts but not others), any "Random Show" where Tim Ferriss and Kevin Rose talk to each other for hours—I've gone back years on this series—anything Seth Godin, and I'll always seek out my friend Andrew Doyle's guest appearances on podcasts, because he's so brilliant.