Yeh, yeh, yeh…do the iTunes shuffle

In my current employment, I’ve got the iTunes loaded up on the office PC (take that Windows Media Player) and uploaded my series of Squid Lord comps for something like three full days of music, should I choose to stay at work that long.
And while I like iTunes’ ability to crossfade tracks (gawrsh, it’s like a radio station in here!) its shuffle play leaves a lot to be desired. I’m curious about the algorithm (or whatever) used to determine what track comes up next, because certain tracks pop up all the time. SoundJam MP does this too (yes, I still use it at home).
However, shuffle play is a great little thing when the collection is large and varied. If post-modernism is all about recontextualizing, then shuffle play is the great recontextualizer. It gives the listener those brief seconds at the beginning of a song to re-hear something, to compare it with the song that came before. It can elevate tracks from albums that were obscured by “the single,” or connections between disparate genres can suddenly appear as if planned.