Here’s what I’m listening to currently:
Comedy Death Ray and Doug Loves Movies have already been mentioned, but also check out Benson’s paid podcast of The Benson Interruption, where he invites his comedians friends onstage to do their act and then interrupts them whenever he feels like it. The last one had Sean Cullen and Garfunkel & Oates and was hilarious. I think he’s planning on releasing one of these a month for a measly couple of bucks.
Even though Jerri doesn’t like it, I love the Pod F. Tompkast, but I am an unabashed PFT fan, so take that as you will. He intersperses his rambling ad libs in the studio with portions from his Largo variety show and other bits of comedy.
The Best Show On WFMU is pure greatness. Host Tom Scharpling has been hosting the show for ten years, and has built one of the strangest pieces of radio entertainment in the history of the medium. It’s a wild mixture of Scharpling rants, mutant call-ins, and free-form comedy sketches between him and partner-in-crime Jon Wurster, with the added extra edge of it being done live, on the radio. The downside is that it’s somewhat impenetrable for newcomers, but if you’re a fan of John Hodgman check out the Christmas 2010 show of The Best Show where Tom, John and a bunch of WFMU staff drink a couple cases of 4 Loco on the air. Madness.
Speaking of Hodgman, his podcast Judge John Hodgman is really, really funny. It’s a shorter 'cast, coming in around twenty minutes or so, where he adjudicates dumb disputes between two friends. It’s cute and hilarious.
The guys from Comedy Death Ray started a podcast network called Earwolf with a bunch of different shows as well. The Sklars host a sports show called Sklarboro Country which is funny, but it’s about sports so I don’t care. Paul Scheer has a bi-monthly one called How Did This Get Made? where they purposefully watch bad movies and then rag on them - funny, but not essential. My fave of the non-CDR ones though is Who Charted?, which started out rough and now has become one of my fave 'casts - Howard Kremer (aka Dragon Boy Suede) and Kulap (aka Scott Aukerman’s wife) run down the top five in music, movies and other charts with a guest. The hook is Kremer knows almost nothing about modern music, nor do any of his guests, so most of it is just ragging on how terrible Katy Perry (for example) is. It shouldn’t be funny, but somehow is.
Greg Proops’ has a newish one called The Smartest Man In The World, where he rants on stage for about an hour about whatever pops into his head. It’s uneven, but he did one a couple of weeks ago where he spent the better part of an hour talking about his loathing of Gweneth Paltrow and I cried laughing.
I recently became a convert to The Thrilling Adventure Hour, another shortish one (half-hour, usually). It’s a live show that parodies old-time radio serials that has a good cast and some great guests: the ubiquitous Paul F. Tompkins, Adam Savage, Nathan Fillion, James Urbaniak, John Dimaggio. Definitely worth a look.