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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.

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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't iTunes shuffle random?.

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Well, that's a nice theory, but all of the songs I put in the playlist have been there since the beginning. There are no new songs. So shouldn't it have set a random order including ALL of the songs that existed at the time Shuffle was first turned on? –  EmmyS Mar 26 '12 at 14:26
    
Hm, yes, it should have. Maybe this playlist was corrupted somehow when it was created? Have you tried creating a new playlist with those songs? Also, do all of the songs have the checkbox checked? –  KatieK Mar 26 '12 at 17:15
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The only success I've had replicating this behavior is when I've unchecked some of the songs in a standard playlist. When I do this and play with shuffle turned on only the checked songs play. Perhaps this is your issue.

If you don't see any checkboxes on the left go to Preferences | General and check the box that says Show list checkboxes.

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Nope, that's not the issue. All songs are checked. –  EmmyS Apr 23 '12 at 18:01
    
Hmm. So it's a non-smart playlist, all songs are checked, you've toggled the shuffle on/off, resorted the list by using the arrow column, and it's still not working? I'm stumped. –  John Rygielski Apr 24 '12 at 12:32
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