U R a Genius!
OK, so color me SOLD on Apple's Genius system. It still has no idea what to do with the Art Ensemble of Chicago, but I will forgive that (I know very few people who know what to do with them! :D )
I still barely touch them on my Mac or PC, but have started using them on my iPod. And it was one of those off-hand sorts of things - I was listening to a Miles Davis song from his Live at Fillmore 1970 CD released a few years ago. I was checking how much time was left in the song and decided to press the 'Genius' button - and it generated a list of 25 songs for me.
The list included some other Miles stuff, Charlie Parker, Weather Report, Herbie Hancock, Charles Mingus, Stanley Clarke, Return to Forever, and so on - not necessarily nailing the sub-genre, but putting together a solid list of songs.
I will continue pushing it to see how it does, but my first look is very promising.