Why aren't my songs from iTunes actually syncing to my iPod? I just put a bunch of songs on my iPod, and most of them worked. But now there’s two more that I need to download and when I drag and drop the files to the "Music" section of my iPod, the songs show up there, but they have that symbol next to them that suggests they are still syncing, and they are gray. But it's been like that for like three hours. So I know they are not actually syncing. Why is it doing this and how can I fix it?
You can also uncheck the songs in iTunes, sync with whatever device you are using, then recheck the songs in iTunes and sync again.  Worked for me.