Album artwork not appearing on all album tracks

Question

Hi,
I have a problem with my iPod 5th Gen 60GB. Not all the songs have cover art, although the cover art is visible in all songs in iTunes. The pattern seems to be that the first couple of tracks of an album show cover art when played/selected, but the remaining tracks have missing cover art.
Some background info. The problem started after I upgraded from Tiger (OS X 10.4) to Leopard (OS X 10.5). I didn't do an actual upgrade, but a clean install. After Leopard was installed I restored my iTunes Library and everything looked and worked fine. After I synced my iPod I soon discovered the problem of the missing artwork.
Based on suggestions on this forum I have tried several things to try and remedy the problem, but have not been succesful yet. Things I have tried:
1. Unchecked the option in iTunes for including cover art on your iPod. Synced. Rechecked the option and synced again.
2. Performed a factory reset of my iPod. Synced so that my complete library was placed on my iPod again.
3. Deleted the Album Artwork cache directory.
4. Configured iTunes so that the currently selected song's cover art was displayed in the little preview window at bottom left. Cycled through all the songs in my library, hoping this would do some black magic voodoo stuff with my library or cache.
The only thing I haven't done yet is to completely delete my current library and create a new one and import all the songs again. Needless to say, this is my last resort, because it's going to take a lot of time (my library location is actually on a Samba share) and it means I will lose all my song ratings.
Does anyone have any other suggestions? Thanks in advance.
Edit: I'm using iTunes 8.1.1

Answer 1

Note: You do not need to buy a song from the iTunes Store to use the online downloadable artwork for that song. You probably know that, but just in case...
If you have manually added artwork to songs, I believe it overrides any downloaded artwork. So as a test, you should select an album (one where the artwork does not appear on the iPod). Select the songs, right click, and +Get Album Artwork+. First, see if your manually added artwork still appears in iTunes. If you get the downloaded artwork showing up instead in iTunes, you can just give the +Clear Downloaded Artwork+ command; your embedded artwork is still there and should show up. I remember trying this to see what happens, and the manually added art had priority in iTunes (but that was a while ago).
If iTunes still uses your manually added artwork, try syncing to the iPod now. See if the downloaded artwork appears. If it does, at least you have album art. iTunes converts album art into a database format that is optimize in size and resolution, to take up the least amount of space possible on the iPod. Maybe there is something about the artwork, for the ones currently missing on the iPod, that prevents the conversion for some reason (too high resolution?). In that case, redoing everything probably will not help, if you are using the same artwork images.
Another thing you can try is to pick a song that does not have artwork on the iPod (but should). In iTunes, right click on the song. Select +Get Info+. In the Info window, go to the Artwork tab. Click on the artwork image and Delete to remove the artwork. iTunes should no longer show artwork for that song.
Sync the iPod.
Do a +Get Info+ on that song again, and go to the Artwork tab. Drag the artwork image you want to use as the album artwork from a Finder window, or from a web browser window, and drop it onto the artwork area in that iTunes song Info window to add it.
Sync the iPod again. See if this re-added artwork now appears on the iPod.
If that works, you can manually delete and re-add the artwork for the songs that do not have artwork on the iPod. Unfortunately, you cannot do the delete part for multiple songs at the same time (as far as I know). You must sync the iPod when there is no artwork in iTunes for the songs in question; you can do several songs before syncing. And you can re-add (at the same time) for a set of songs that have the same artwork, by dragging the artwork to the bottom right corner display on the iTunes window (instead of the the +Get Info+ window for a single song).