When I manually add songs to iphone 4s many appear gray and won't play. How do I fix this?

When I manually add songs to iphone 4s many appear gray and won't play. How do I fix this? I have the manually manage music button checked, and I can play them on itunes, but on my iphone they appear gray and won't play.  There doesn't seem to be any reason, as one song from an album will play, but the other 9 won't....

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