Jesse Thorn's other show may appeal to a more niche audience, but it's my favorite thing ever.
It's a podcast called Jordan, Jesse, Go! and it's just Jesse and his college friend Jordan (with occasional guests and callers), talking about shit for like an hour and a half every week. They are both endlessly charming and funny, and I recommend getting like 20 of those episodes for long car rides, or super boring family events, weddings, Bar and Bat Mitzvahs, that sort of thing.
You can put them on your ipod.
Annie - you can put them on Wiley's ipod.