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Itunes device authorization issue?

I am experiencing a problem with a recent album that I downloaded from the I Tunes store.

One of the favortite songs from the album will not play on any device, and I also have an issue trying to play song on my I Mac.

When I try to play the song, a prompt asks me to authorize the song for the device. I enter my information and another prompt tells me the song is already authorized for the device. However when I try to play the song, I am sent back to the original prompt.