Songs will play in iTunes but not play on iPod!

This is very weird. I have 44 songs that are not working right.
A few months ago I moved my music files to one central location on my computer (aside from iTunes). I wanted to get rid of duplicates and songs I just didn't want and more importantly I wanted to make sure the names were all correct.
Oddly enough the songs in questions I did not have to change.
I synced my new iPod to my iTunes. I played a few songs and when it got to 1 of the 44 it just skipped over it. I thought this was weird so I went through artists and found the song that way, I selected it again and it wouldn't play.
I tired playing the song in iTunes - the song played.
I found it on my computer - the song played in Windows Media Player.
Before I did all of this, on my old iPod - the song played.
In fact all 44 of the songs used to play and everything was fine. (I use my old iPod for my car and my new one for jogging, but I don't want to sync my new one until I solve the problem I just don't want to risk losing the songs)
So I looked in the iTunes files - there is a file known as "Not Added" within the "Automatically Added" File. The songs in question were in that file. Which is weird because I never had this problem before...I didn't change anything about these songs.
I took one of the songs out of the "Not Added" file and I put it in the Automatically Added file and it seemed to add it. I tried syncing againbut the song would still not play.
I tried moving the song directly to the iTunes "Music" File. It made its own file with the artist and all - it hadn't been there before. So I tried syncing again but it still wouldn't play.
Yes - I have plenty of room on my iPod
Yes - I have tried restoring my iPod
No - There is not a little explanation point next to the song - The song is located and it plays in iTunes just fine.
I am at a loss. Someone please help me!
Thanks!
~Jess

Select the track that is giving you a problem, then go to Advanced menu and select "Create AAC". Then try using that new AAC track on the ipod and see if it works.
I had some tracks that I had gotten onto my system from a CD. It ended up that my CD drive as on its last legs and had captured the tracks with some errors.iTunes was able to play through these errors, but my iPod was not. Having iTunes re-transcode them fixed the problem that kept them from playing on the iPod. Another solution would be to re-rip the tracks from your original CD. If you bought them on iTunes, re-download them.
The bottom line is that the tracks likely have some errors in them that iTunes can play through, but the iPod cannot.
Hope that helps,
i

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