Some iTunes purchased songs will not play on iPhone.

Some of my songs that I have purchased from iTunes will not play on my iPhone but will play on my MacBook Pro and iPad - what can I do to fix this.  This problem has been happening for around a week now.  At first it was 1-2 songs but now in a playlist of around 80 songs approximately 1/4 of the songs will not play.  When the song comes up next in the playlist it will not only skip that song but will also skip past 1-2 other songs.

Hey brewmaster1967,
Does this happen with any other purchased content? Download some of the free on iTunes store songs.
Deauthorize the computer and play/authorize the song in iTunes again.
http://docs.info.apple.com/article.html?artnum=93014
Try re-creating the iTunes Library.
http://docs.info.apple.com/article.html?artnum=93313
Jason

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