Why are songs greyed-out in my iPhone's sync queue?

I fired up iTunes for the first time on a new computer and plugged-in a 2 week-old iPhone 4s to sync about 250 or so songs that were pre-existing on the computer.
The music is not purchased through iTunes; merely ripped from CDs ages ago. It's music that existed on my prior iPhone (4) with no problems.
Now, the music won't sync to my new iPhone. It shows up in iTunes, on the device's song list - but greyed-out. It appears to be in queue to transfer, but it won't sync. I have purchased music on my phone that I downloaded via wifi that works fine...
Any ideas? This is intensely frustrating.

I forgot to mention that when I look at the playlist that has been tranferred to the iPhone all the ones that won't play and are greyed out have a sync symbol next to the check mark.

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