I jumped into 2004 last month, purchasing a moderately priced digital media player through Amazon.
It's only 4 gigs, but it gets the job done -- that job being podcast playback. Talk radio entertained me through long hours farming, audiobooks have passed many a road trip, and now this sort-of cheap device can bring that fun anywhere I roam.
If you're similarly pleased by podcast, please persue:
You Look Nice Today
Matt recommended this, and I'm glad he did. If you enjoy the live episode, "Live!: Baby on a Dog", you should subscribe to the feed.
(The format and tone of this show is imagined Phil and I would be creating when, a few years back, he suggested we record conversations via Skype for our own podcast. I went to Best Buy over my lunch break to buy a USB headphone/microphone combo, set up Skype, jotted down some ideas, and was ready to claim spot atop the podcasting world. Phil's interest waned. Gav claimed ownership of the headset; then, since it was made by Logitech, it broke. Goddamn Logitech. You buy a magical, life-changing universal remote from them for a premium price, and less than 2 years later it's wonky, and their customer service suggests you do a safe mode reboot even though they know that won't improve the response of the failing buttons, and they say, "Oops! It's only got a one-year warranty! Suck it!" Anyways, what I'm trying to say is: I should have a podcast, but I don't.)
The Adam Carolla Show
More hits than misses. The news segments are often daily highlights, spawning humorous tangents and prolonged commentary.
The Sound of Young America
Recommended only if you've heard of the person being interviewed. Shows featuring comedians are the best. Try it out by listening to the interview of Paul F. Tompkins, which includes some good stand-up clips.
This American Life
You already know this, because you're white and middle-class, but it's consistently great. RELEVANCY ALERT: if you want to know what the fuck prompted the U.S. economy to turn to shit overnight, listen to "The Giant Pool of Money".
If YOU have any additions to this small list of good podcasts, please post them in the comments.