I'm sure this has been asked before, but I can't seem to search for the right terms. I have a playlist in iTunes that has over 200 songs in it, yet when on Shuffle, iTunes plays the same 15-20 songs over and over. I created the playlist over a year ago and listen at work almost every day, and there are dozens of songs that have never been played unless I turn off shuffle and manually select them to play.
I know Shuffle is random, and that true mathematical randomness means it's just as likely that you'd hear the same song 10 times in a row as that you'd hear 10 different songs, but isn't there some way to force iTunes to play all the songs in a playlist when it's on Shuffle?
I'm currently running iTunes 10.4 on a Mac (Snow Leopard), but this is true on other versions and operating systems as well.