One particular song won't play on shuffle

My shuffle has been working fine, but I'm trying to load an audiobook and play it on my shuffle. All the other ones will play fine except this one. There's no problem with the file. Does the shuffle have a hard time handling long songs?

Select the song.
Get Info.
Make sure the box Skip On Shuffle is not checked.
What if I can't uncheck the box? I can see that it's checked, but there's no option to uncheck it.
This may or may not be important, but when I push play, the green light comes on and stays on.

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  • TS1389 Only one song won't play after authorizing my computer. I authorized it over and over. I even deauthorized all computers, and still same results. How can I fix this ? I'm using a MacBook Pro with iTunes 11

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    <Edited by Host>
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