Steven Levy over at Newsweek has a great article on the iPod's seemingly non-random random function. See I wasn't crazy when I wrote about the rock block, but I do recall a couple people wrote me explaining much of the same thing Levy heard. I took a few courses on statistics and understand how these things can happen, though they seemed to happen with such frequency that it seemed uncanny. Of course, like Ev, I remember when the Pyra music server seemed to play Cake incessantly, even though there were hundreds of other artists on the drive.
Random really is random, and it's human nature to make sense of it all, looking for patterns wherever you see them and doing your best to make order from the chaos. It's what humans do well and what I notice myself doing everyday.
My 2000+ song libary still constantly surprises me by playing