Much has been jokily written about the random shuffle function on the iPod and how it uncannily manages to pick tracks to match your mood and situation. I have more than 7,500 tracks on mine and this afternoon I had a friend from my university days over. My iPod was on random shuffle playing through speakers and in the two hours she was here it managed to serve up first a selection of tracks that we used to dance to and most spookily of all, a really obscure track from a really, really obscure 1980s band that sank without trace which is indelibly linked with that friend and one other in our heads. I haven't played that track for months, if not years.
rodriguez - hell I agree. My PMP140 is hell for that, I use it now exclusively for video and My palm treo for music. But the PMP remains my little back up drive for the audio. Random on the ipod is as said true random but Personally a lot of my albums have to be played in order to make any sense audio wise so I just use playlists.
The last report I saw on this in a newspaper (Guardian perhaps?) said that the next generation shuffle was going to be less random as the true randomness had made people think it wasn't as random as it really was.
I expect part of the spookiness is just that you noticed the tracks because of something else and so made a link between two exclusive events.