I’m all for strange juxtapositions (I might post some of my playlists sometime), my gripe is that random doesn’t do this very well. My music collection is not just an amorphous sea – there are myriad connections between songs and a good comp should exploit this. Commercial compilations are generally not much good, because they try to meet very general criteria and these journeys are really very personal. (Oh, and you have to buy again songs you already have.)

I don’t use iTunes often, but doesn’t it have a star system? One of my many complaints about it, though, is it doesn’t give much away about how it chooses songs. Maybe it doesn’t actually take any notice of the stars..?

http://www.hak5.org/forums/viewtopic.php?t=828&start=0

I gave up trying to produce the perfect mix tape or playlist about 30 years ago in college. We were all reading The Dice Man and Lord High Randomfactor was king.

What I want now is this. A plug in for Winamp, iTunes and my personal media player. It should make it easy for me to “Play any track” from my entire collection. There should then be 3 big buttons “Love, Skip, Ban” that I can hit while it’s playing. The random shuffle should use me pressing these buttons to adjust the randomness. I may have a bunch of 90s dance music in there but I don’t actually want to listen to that 4-4 beat much any more. If I keep hitting Ban or Skip, it should fade away.

When it works well, pure randomness works well and begins to sound like an old John Peel session. Miles Davis to Robert Johnson to Ivor Cutler to Ozric Tentacles to Red Snapper to Mice on Mars to John Martyn. Lovely.