iTunes not playing all songs in a playlist 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.
iTunes defines the random order of the tracks when you first specify set "Shuffle".  (This is so that the skip forward / backward buttons work in a reasonable manner.)  If you never turn Shuffle on or off, that order is never changed.  Just disable and then re-enable Shuffle to get a new random order of tracks.  

For more detail, see Why isn&#39;t iTunes shuffle random?.