I have 744 songs in iTunes at work right now. Today I've listened to 42 songs out of my complete library which were "randomly selected" by iTunes. Then they started repeating. It got pretty ludicrous. I noticed, and started hitting ctrl-right arrow to move on the the next tune. Five straight last played today. Changed the sort order, hoping that'd help, and ordered by date played. The arrow for what song was playing just climbed right up the list, every song picked having been played today.

I hit "next song" an obscene number of times, and when the needle came back up I was staring "I Ain't the One" in the face, which was last played 2/13/2004. Phew.

I'd heard complaints about the non-random nature of iTune's random selections, but had never seen it up close before. Before today, anyhow.