Playlist shuffle problems

I'm having issues with playlist shuffling on my iPhone 4, and the only discussion I found with the same problem remained unanswered.  I have a playlist of various classical music that I want to shuffle randomly, and it won't.  If I play it in order, all 53 songs will play and can repeat in order.  If I select "Shuffle" from the list of songs, or if I hit the blue "shuffle" icon on the cover art, it changes from "1 of 53" to either "1 of 8" or "1 of 9" (depending on which song happens to be playing).  The smaller groups don't seem to be based by artist or by album, but I can't get it to shuffle all 53 songs. I tried making a smart playlist by genre, and I tried making the playlist manually.  Nothing seems to work.  I have another mixed playlist with various artists and multiple albums, and it functions normally: I can get it to shuffle randomly through all 51 songs across albums and artists no problem.  There must be some property of the music files or the playlists that I'm missing that's causing this bug, but I'm at my wit's end.  Any suggestions?

Do all the songs in your playlist have a check in the box to the left of each song's name?  Songs without a check will be ignored unless specifically selected to play. If you don't see the checkboxes, go to iTunes > Preferences > General and check "Show list checkboxes".
To check or uncheck all boxes on a Mac with one click, hold down the Command (cmd) key and click on one of the checkboxes with the mouse.  You can use this in a library, a playlist or in search results.
If the check marks are not the source of your problem, select one of the songs that won't play when shuffling. Open the song's information window (cmd + I or File > Get Info) and click the Options tab. Check that "Skip when shuiffling" is not checked.

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    Thank you so much for propmtly coming to my aid! Unfortunately, I have done both of those things and yet the issue remains, arrrgh.  Just for complete clarification(not do to a lack of understanding on your part, but possibley for future viewers), it's not that it won't shuffle, it's that it doesn't play anything after the current song has finished. I have to manually get it to play something else.  once I turn off shuffle it plays thru my playlist fine.  I tried to play it with repeat on (and yes repeat all not just 1....not that dumb thank god.) and the problem persists.  It's pretty frustrating and I am starting to think that maybe something went awry in my recent update of itunes.  Again, thank you for responding so quickly.  If you have anymore suggestions it would be greatly appreciated.

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