The Word DJ

This is trivial, but actualy seems to work surprisingly well. Bring up iTunes (or your audio player du jour), and type a random word into the search box. Then play all the matching tunes that it finds. For example, in my (somewhat boring) playlist, I just entered "river" and listened to three versions of Take me To the River, Somewhere Down the Crazy River, and Renée Fleming singing River Songs. Color names, animals, cities—just as long as you get a handful of matches, it doesn’t matter.