Dear ChiCat (or anyone looking for a new podcast),
Hollywood Handbook - if you want a sample episode, they interviewed Ben Stiller a couple weeks back who is absolutely the biggest guest they've landed by a lot. And the whole time they just kept asking him if he would help them get Adam Scott get on the show since they work on Severance together. Very Norm MacDonald-esque humor.
Blocks with Neal Brennan - he was the cowriter of Chapelle Show, and has been very open with his struggles with mental health. So he interviews other comedians and really gets into mental health and tendencies. As someone with a psych degree and a love for stand up, this has jumped to the top of my list.
Bad Friends with Andrew Santino and Bobby Lee - just plain fun
Two Bears One Cave with Bert Kreischer and Tom Segura - I think Bert Kreischer is such a spectacle I could just listen to him talk to anyone
Macrodosing - PFT from Pardon My Take and Arian Foster take on subjects from conspiracy theories to The Revolutionary War to cryptids to The Ocean. It's all awesome. The first hour is usually the crew catching up which isn't fun if you don't know the personalities, but it is a really great group of personalities for such a wide array of subjects
Nateland - Nate Bargatze's podcast
Confused Breakfast/The Rewatchables - fun info about movies we've all seen a bunch. Confused Breakfast is three guys mid-late thirties that mostly review movies from their (our) childhood. Then Rewatchables is hosted by Bill Simmons, so even if they were to do the same movie it's a wildly different perspective.
You Made It Weird - Pete Holmes interview show. He can definitely be overwhelming at times, and has a tendency to interrupt his guests when he gets excited. It can be offputting, but his positive attitude/outlook on life is worth the listen.