Okay so here's one more clue that, yes indeed, I am a 20-something white guy who grew up in an affluent suburb: I'm about to recommend a podcast produced by National Public Radio, which I listen to regularly on my iPod. (Further evidence: #13, #23, #24, #28, #42, #61, #72, #80, #81, #90, #94, #110, #111, #112 from this list.)
Now that that's out of the way: check out Jazz Profiles, which is a series that NPR did a few years ago profiling many legendary jazz musicians. They're gradually posting all of the episodes on the web. I get the sense that they tried to focus on musicians who were still alive at the time but might not be for much longer, though they also cover the super-important figures in jazz like Armstrong, Ellington, and Basie that you couldn't get away with not saying something about. The shows are hosted by Nancy Wilson, a contemporary jazz singer, who has a very nice voice and every now and again interjects little personal comments.
I've found most of the shows to be interesting, and some exceptionally so. In particular, check out the episodes on pianist and band leader Jay McShann, bassist Milt Hinton, and trombone player Al Grey. You can download the shows from the website, or subscribe to the podcast and a new show will appear in your feed about once a week.