Cannot play songs purchased with gift card (on my iPod on)

I just purchased the King Kong soundtrack on iTunes with a gift card I received for Christmas. I downloaded the songs onto my laptop and transferred them to my iPod (video, 60 GB). When I try to play the songs on my iPod, they will just be skipped over to the next track. (I can play them off my iPod when it's attached to my laptop, or my G4 tower at home, which is also Authorized).
I've purchased other songs with my account in the past and they play fine. I checked the song info. in iTunes and the account information is identical to the other purchases. The only difference seems to be these were purchased with the gift card (which the file info. doesn't indicate).
What do I need to do? Thank you brilliant folks out there.

Alas, did not work. Tried playing a few songs in iTunes, copied those songs over to the iPod, no dice.
I manually manage my songs on iPod, so I'm hesitant to just auto-sync and see if that would solve it, but I may try that if nothing else works...

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