The Joe Rogan Experience (Joe Rogan) https://podcasts.apple.com/us/podcast/the-joe-rogan-experien... Love him or hate him, Joe consistently gets some fascinating guests on his podcast, and he isn't afraid of getting into some deep topics with some of most brilliant minds out there.
Conan O'Brien Needs a Friend (Conan O'Brien) https://podcasts.apple.com/us/podcast/conan-obrien-needs-a-f... I'm a recent convert to this podcast, but I've had a lot of fun listening to it over the last few weeks. It's typical Conan, but in podcast form, so if you're a fan then this one is a no brainer.
Andrea Savage: Grown Up Woman #buttholes (Andrea Savage) https://podcasts.apple.com/us/podcast/andrea-savage-a-grown-... Yes, that's the title, including the hashtag. If raw, often awkward (on purpose?!), and sarcastic humor is your jam then you'll feel right at home with this podcast. I've always thought Andrea Savage was an under-rated comic performer, and so happy she's got a new podcast and TV show (have you seen "I'm Sorry" yet?!).
Id10t (Chris Hardwick) https://podcasts.apple.com/us/podcast/id10t-with-chris-hardw... I've always enjoyed Chris and his goofball sense of humor. He's about as affable a podcast host as you could ask for, and he brings a lot of insight into all things nerdy and geeky.
WTF with Marc Maron (Marc Maron) https://podcasts.apple.com/us/podcast/wtf-with-marc-maron-po... Marc gets deep with his guests, and sometimes he gets a bit too angsty, but it is what it is and he is what he is. He's got interesting guests from the all over the map (TV, the art work, and lots and lots of musicians), and he's the only podcaster I know of to have ANY President of the United States to visit and chat, so he's got that going for him.
Inside of You (Michael Rosenbaum) https://podcasts.apple.com/us/podcast/inside-of-you-with-mic... Smallville's Lex Luthor (among other things) brings all the realness to his podcast, which more often than not prompts his guests to do the same. Whether it's how the set of Guardians of the Galaxy was or what it's like in a mental health retreat (and anywhere in between), there's something for everyone.
Office Ladies (Jenna Fischer and Angela Kinsey) https://podcasts.apple.com/us/podcast/office-ladies/id148031... Fan of The Office? Perfect! Pam and Angela, or rather their real-life human counterparts, discuss each episode of the The Office from start to finish and give behind the scenes details, have special guests (cast and crew), and more.
The Comedy Store Podcast (Eleanor Kerrigan and Rick Ingraham) https://podcasts.apple.com/us/podcast/the-comedy-store-podca... From the World Famous Comedy Store in Los Angeles comes an unfiltered view into the lives of current and past stand-up comics, from all levels of fame. If you want all the comedy gossip from the folks who were there, this is the podcast to listen to.