HT1535 Manual Sync not Syncing

On my mac, I've dragged the particular playlists I want to be in my iPhone into my iPhone. When I click "On this Phone", it has listed what I want. However, it's all in gray, and it's not synced up. When I hit sync, it goes through the process and acts like it syncs, but nothing on my phone changes. I still have the same playlists/artists/music I had before, and not any of the new stuff (even with my recently added playlist). What's going on here?

Unchecking and rechecking songs worked for some but not all songs.  Recreating the library, http://support.apple.com/kb/HT1451 , works. 

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