I've always loved this particular math factoid/game/mind-boggler:
Wired News: My IPod for a Random Playlist (sic - iPod is the preferred spelling)
To illustrate his point, [mathematician Jeff] Lait referred to a phenomenon statisticians call the birthday paradox. Roughly stated, it holds that if there are 23 randomly selected people in a room, there is a better than 50-50 chance that at least two of them will have the same birthday. The point: Mathematical randomness often contradicts our intuitive expectations of randomness.
On the larger point, randomization: I'm significantly better now, but when I was younger, I made many decisions after applying some 'randomization' protocols (such as I always carried around several Chinese coins - and gave different values to heads or tails, flipped them and added up the numbers; or used dice; or other tools like the added-up page numbers of a randomly opened book). Yes, I had problems making decisions sometimes. Some folk resort to tarot cards, or media pundits - I used my own home-grown methods. Did I mention that I used to ingest plenty of inebrients?
SoundJam's randomization algorithms (and hence iTunes too) always seemed a little to prone to repeats, so I've worked many, many an hour creating playlists that eluded the need for 'true' randomization. I still use the artfully created playlist instead of using Smart Playlists, even though that particular tool has improved, a bit. My playlists still give better results.
On this score, Apple's iTunes takes the lead with a feature called Smart Playlists. It allows you to set all kinds of conditions as to what songs do and don't get played. For instance, you can tell it to select songs at random but to select only tunes that haven't been played in the last two days, or week.- Wired