In one of those acts that I try to rationalize as a form of ethnographic research (I do write a lot about technology and culture, after all, and these ideas have to come from somewhere), I’ve started playing with the smart playlists feature in iTunes.

I love playlists. They appeal to that part of me that used to agonize over dance tapes, or what to do with that 4′ 37″ left over at the end of the tape when I’d finished copying some album. The virtue of smart playlists is that they let you tell iTunes to choose songs based on certain criteria, rather than choosing specific songs– which in my case tends to encourage my listening to the same 200 songs or so.

To combat this, one of the smart playlists I created selects the highest-ranked songs that I haven’t listened to in a long time– the classics and sleepers that have fallen to the bottom of your record collection, but deserve another spin (to mix my metaphors). It looks for 4- and 5-star rated songs, then chooses a selection of the ones that have been least recently played: this guarantees that they’re uniformly great songs, and ones that I haven’t heard in a while. Add live updating, so once a song plays, it disappears from the list, and another takes is place. Then put on random play, so you don’t get 14 Santana songs in a row.

iTunes gets lots of attention for its success as a business, but working with it, I get the feeling that I would get with the Mac c. 1987 (I couldn’t afford one before then): here’s a technology that is at once simple and extremely deep– not so much because of what it can do, but because of what I can do with it. It’s a great example of a tool that encourages creativity rather than just productivity.

[To the tune of Lynyrd Skynyrd, “Free Bird,” from the album Millienumium Collection.]