The Apple Blog » Random Play Messes with our Heads:
"I came across a very interesting article on Wired that explains the general dismay people have with the seeming lack of randomness that results from random playlists. Dan Goodin (the writer) explains some of the lengths he’s gone to in order to achieve random bliss - going so far as to touch on Real Player, MusicMatch, Winamp, and concludes with iTunes. He even tried running a playlist through randomizing algorithms in different music players…talk about dedication.

It gets interesting when he speaks with a mathematician (Jeff Lait, creator of randomm3u) who explains the real problem. It’s all in our head. The fact is, that algorithms can make a list completely randomized - but that resulting random list may not fit with what we EXPECT out of that randomization. Interesting, but makes sense.

Dan concludes that iTunes is the current leader of Randomization however. Why? (Those of you answering, “Because it’s Apple!” would be wrong. Mostly.) Because Apple (ok, you were partially correct) was insightful enough to include Smart Playlists. As most of you know, playlists can be created by random, with any number of stipulations applied to create that perfect list of songs.

So next time your iPod Shuffle is disappointing you, and you yell out loud, “Life is random, my apple!” remember that it’s your noggin that’s really the dissapointment…"