Check out Bill Simmons’ old podcast, The B.S. Report. Bill Simmons is the former ESPN analyst, journalist, and founder of Grantland who was fired from ESPN last spring for “no one really knows why.”
I’m a huge fan of his, mostly because he’s interested in a lot of the same things I’m interested in: sports, film, and comedy.
His old podcast is mostly interviews with sports figures, but it’s also many other things. My favorite interviews are those with comedians, of which he has a decent number. And they’re all top notch comedians and writers who he invites on the show because he personally likes them, not because they’re promoting something. Bill Burr, Louis C.K., Jimmy Kimmel, Lena Dunham, etc. He also knows a surprising amount about comedy for not being a comedian and does a lot of great research for the show. He asks interesting questions that aren’t always about comedy, which is also a nice change of pace from the typical comedian interview.
You can find The B.S. Report on Youtube here and his new podcast, which I have not had the pleasure of hearing yet, here. I particularly like Simmons’ interview with Larry David, head writer of Seinfeld.