I have recently gotten a new Mac and the newer iTunes version did take some getting used to. Personally, I transfer only select songs actually to the iPod via playlists.
Does the music play from iTunes (so it IS "in" there, right?), and you are having trouble moving it to a Playlist?
Can do with individual artists, too, but personally I prefer a Playlist. You could skip the "How to make a Playlist" part below and go straight to "*" with italics instructions below...
Try (assumes your iTunes version new, and this is how it looks on a Mac - not sure how could look different on a PC):
Pull up "Music" from the strip across the top of the window to show what songs you have in all of iTunes
Go to very top menu: File, select New->Playlist
Drag songs, albums, or artists from all choices over to new Playlist on the right
Click "done" when finished with Playlist, then you should see your new Playlist on the left side menu under "Music"
Attach your iPod if not already done - should present itself on the strip of choices across near the top of the window (NOT the very top of the whole computer).
Click the icon for you iPod to show what's on the iPod. Usually pops up "Summary" -> change this to "Music" (again on the strip near top of window). You should see all of the iTunes choices.
Check the box beside your new Playlist (*OR if you skipped the "Make a Playlist" part, can choose "Artist")
Go to the bottom of the screen, right side, click "Apply" to sync.
Eject.
Hope that helps.
My husband, actual computer guru, always tells me to just Google any computer tech question, because someone has probably had the same one.
