Why are songs showing up GRAY and UNPLAYABLE on my brother's itouch?!?!?

ApPPLECHUNX

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i think it's a 3rd gen, 32 gb whatever.

point is, i had 2000 songs in my itunes. on my touch nano, they sync and play just fine. but not all 2000 fit so my bro is switching me ipods. well, on the itouch, every few songs (every 20 songs or so) one song will pop up but i cant click it. from the songs list, its gray and unclickable. unplayable. i have no idea whats wrong, all my songs should be the approrpriate format i mean they fit on my nano! what the heck! please help me :C
 
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