Songs are not loading onto my iphone from itunes (gray "ghost songs"

Hi there,
I'm set up to manually manage my music in Itunes (Mac) with my Iphone 4s. Yesterday I switched to automatic syncing, a bunch of extremely random things happened, and all my music disappeared on my phone. I switched back to manually managing music, and now songs that I drag from my itunes library only show up as those dreaded gray "ghost songs" once they're dragged in. The same goes for if I "autofill" from a specific folder, and when I go back to "automoatic syncing".
However this is strangely limited to songs purchased on Itunes. Songs that have been ripped from CDs have no problem loading, and show up black and playable in itunes.
I have restored to an earlier backup, but this didn't resolve the problem.
I'm about to put both my laptop and my phone through a window.
Somebody? Anybody?

Carab81,
You have Sync Entire music library option selected?  Double check your enabled settings from under your iPod's Summary tab as well to make sure they are not interfering with this configuration.
B-rock

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