Razor, is the song in MP3 format or the iTunes format?
The iTunes format, (AAC).
Ok, copy that file to another directory on your computer. Then using iTunes, delete the file out of the playlist. Then re-sync your iPod. Copy the file back into the directory, add it back to the playlist, then re-sync your iPod again.
OK, I just tried this and it didn't work.

I have no idea why; there's no logical reason why it shouldn't. The file plays fine on the PC.
maybe it's time to send apple an email?
Yeah, I think so ... or see if there is an iPod users help forum out there somewhere.
the only"problem" i ever have gotten is multiples of the same artist in my ipod....like when i scroll thru and there's 2 listings for the same artist. y does this happen? anyone know?
the only"problem" i ever have gotten is multiples of the same artist in my ipod....like when i scroll thru and there's 2 listings for the same artist. y does this happen? anyone know?
Check and see if there is an extra space before or after the name. If there is, it will be read as a completely different name. Delete the extra space and everything will roll up to the one artist.
see ive done that... i'm very meticulous so y do i still have multiple listings of foreigner?
Razor, is the song in MP3 format or the iTunes format?
The iTunes format, (AAC).
Ok, copy that file to another directory on your computer. Then using iTunes, delete the file out of the playlist. Then re-sync your iPod. Copy the file back into the directory, add it back to the playlist, then re-sync your iPod again.
OK, I just tried this and it didn't work.
I have no idea why; there's no logical reason why it shouldn't. The file plays fine on the PC. 
Aight, I'm gonna try and help you with this. When attempting what Tyler said, did you use the "Find file in explorer" option that pops up when you right click a song? What is the original source of the song? CD? MP3 downloaded from the net? You on Windows, or OS X, or Linux?
Razor, is the song in MP3 format or the iTunes format?
The iTunes format, (AAC).
Ok, copy that file to another directory on your computer. Then using iTunes, delete the file out of the playlist. Then re-sync your iPod. Copy the file back into the directory, add it back to the playlist, then re-sync your iPod again.
OK, I just tried this and it didn't work.
I have no idea why; there's no logical reason why it shouldn't. The file plays fine on the PC. 
Aight, I'm gonna try and help you with this. When attempting what Tyler said, did you use the "Find file in explorer" option that pops up when you right click a song? What is the original source of the song? CD? MP3 downloaded from the net? You on Windows, or OS X, or Linux?
Yes, I used Explorer and moved the file from its directory in the iTunes Music folder. It was originally ripped from a CD and I'm using Windows XP.
OK, I just found a iPod forum where there are a lot of people discussing this problem. Seems to be a bug in the iPod Classic software, but nobody's managed to come up with a way to fix it yet.