I listen to a lot of podcasts. Over the last couple of years they have become my main media of choice. I commute to work via bus or streetcar so I have time to kill every day. Owning first an iPod, then an iPhone, enables me to listen to sound files (mp3's) during my travels. It used to be music, but now it's mainly comedy or film-related podcasts.
My very first was an episode of Battleship Pretension (#128 w/ guest Frank Conniff, an alum of MST3K) in August of 2009 which I was pointed to by the MST fan site Satellite News. What I found was an informal chat between Frank and the hosts Tyler and David on the subject of so-called "bad movies" and how some people love them, or at least find them fascinating. I liked the hosts enough to check out other episodes, and I still regularly listen to their show.
One of their earliest guests was Matt Belknap who runs the AST (A Special Thing) website and record label. His stories about attending comedy shows in L.A. and posting reviews online inspired me to check out that site and some of the podcasts he produces, namely Jimmy Pardo and Doug Benson (and lately, Greg Proops).
Podcasting is an ideal medium for stand-up comedians as they are inexpensive to record and distribute, allow for free-flowing conversation, and can be released uncensored. Most appear with new episodes on a weekly basis, free of charge, though some have figured out how to monetize their product with paid subscriptions (Pardo's Never Not Funny) or "Bonus" episodes (Benson's Doug Loves Movies & The Benson Interruption - for sale via AST or iTunes).
Marc Maron's WTF has gotten a lot of well-deserved mainstream press recognition as he is funny, insightful, and a great interviewer.
Another early podcast I listened to a bunch was filmmaker Kevin Smith's SModcast.
In May of this year he launched the SIR Network which is maybe a dozen programs with him and his buddies bullshitting about various topics. I was a regular for awhile but I burnt-out on it and haven't listened in months.
What I did stick with was the Stitcher app Smith used to stream his product. One can regularly listen to hundreds of shows with this tool (as long as you have a WiFi or 3G connection to the web). Not every podcast out there is a available but a lot of them are. It's a good way to casually check out a show without actually downloading it.
Earwolf is a network that I DO regularly listen to as it features at least half a dozen great shows. Founded by Scott Aukerman (Mr. Show vet, host of Comedy Death-Ray - now Comedy Bang Bang) and Jeff Ullrich. Earlier in 2011 they ran The Earwolf Challenge which was the first (and to date, only) reality-show podcast competition. It was a blast to listen to (3 new episodes a week!) as 10 shows entered, and 1 show walked away with a year-long distribution deal. What was so great about it was that podcasting was looked at as a craft in and of itself, while judges and participants struggled to define what makes an effective show. Earwolf also has an excellent iPhone/Android app that enables you to stream content directly to your device.
Other recent favorites:
I would be remiss in not pointing the curious towards Christine E. Taylor's blog Podcasting Changes Everything. She has interviews and features about comedy podcasts and has turned me on to few new ones. It's a fledgling medium and she is one of it's most fervent supporters.
I listen to a lot of podcasts, and I have only mentioned a handful above. No doubt I will return to this subject in the future…