iPod won't play certain songs that iTunes will

[empire89]

Ok so about 800 of my 1200 or so songs won't play on my ipod, but play fine in itunes. I downloaded the latest version of iTunes last night, checked for any iPod software updates, and tried again. Nothing. I then restored my iPod, and tried again. Still not helping. One thing I noticed: I'm using a new laptop and transfered my old library on to this computer. Songs that I downloaded directly to this PC work but any songs that were transfered are the ones that won't play. I have already authorized this computer for playing songs from my other iTunes folder. Please help!!!

P.S. when I select one of the messed up songs on my ipod it sends me straight back to the main menu. if its on shuffle, it just keeps skipping till it finds a playable song.

Thanks