I've had my mp3 player on random on 4 separate occasions but only for a short time - total playing time of not much more than an hour I'd say. Despite this (and the fact I have over 5500 tracks), 'Perfect Skin' by Lloyd Cole has come up 3 out of the 4 times. Not that I'm complaining...

Does anyone find themselves occasionally hearing what seem to be remarkable musical coincidences?

My iPod once threw up MIA's Paper Planes, followed immediately by The Clash's Straight To Hell, of which the former sampled.

...on your media player you effectively let it off the leash, so that it can run off into the distance and ignore your shouted instructions for it not to play with the Zodiac Mindwarp.

My copy of itunes went through a phase of repeatedly attempting to sneak Lou Reed’s Adventurer into what was supposed to be a series of random playlists. Eventually I got fed up and removed the entire Set the Twilight Reeling album from my library.

itunes has since taken a liking to The Liar's Club by The Webb Brothers, which I am happy to go along with for the time being.

It rarely plays anything by a black artist

Many the argument I've had with people on the true meaning of "random".

Some science type will try to explain the Apple algorithims but cannot tell me why it will play 6 songs from the USA Mix of the Holy Bible within 30 tracks but not have another artist duplicated...

Seems to happen far more on a hard drive iPod than the flash memory ones.

I sympathise. My ipod loves the Beta Band even though I've only got one album on there - I haven't removed it yet but I'm tempted.

Also, it has recently decided that one track by an artist is not enough and regularly plays two tracks in a row. This morning it was The Raconteurs (one from the second album then one from the first). The other day it played two versions of the Get Carter theme one after the other. I had no complaints on either occasion but it still freaked me out a bit.

I have also become frustrated by my Creative Zen's idea of random which, as you say Mr Loud seems to home in on cetain albums, despite having 5,500 tracks to choose from.

I now just set it to All Tracks and play songs alphabetically -

I've just had Darling Corey -JSD Band, David Watts - The Jam, Day Old Blue - Kings of Leon, Deacon Blues - Steely Dan, Dead Finks Don't Talk - Brian Eno and Dear Catastrophie Waitress - Belle and Sebastian as I travel home on the bus

a far more rewarding experience I find.

...than I should. Costello, that is, and I do have a fair chunk of his output. but not that much. And why is it always some of the dirges from "North"?
Agree with the reluctance of the i-pod to choose black artists. Jeez, after a year of jazz, it can even find way more Gerry Mulligan than Sonny Rollins.

My ipod read my mind recently. I was thinking about 'Bleach' by Nirvana and that I hadn't listened to it for ages, then the cover appeared on the cover flow thing and 'About a Girl' came on shuffle.

Weird

I was walking into work 7am feeling weary and half-asleep and got 'I'm So Tired' followed by 'Faust Arp' by Radiohead which starts 'wakey wakey rise and shine' in a rather beautiful, gentle way.