Q: I have a 60GB iPod photo, and for some reason last week, it stopped displaying album art when playing music. When it is connected to iTunes, all the album covers are still there.
A: We’ve had a flurry of readers report album art issues on the iPod, although the details vary.
Some users report all album art spontaneously disappering from their iPod’s entire collection, while others report missing art from only selected songs, and some say their album art displays, but with the incorrect photo-song associations, as if all their album art had become shuffled among their library.
In all of these cases, assuming your artwork is correct in your iTunes library, we recommend one procedure as an album art panacea:
Connect your iPod and allow it to synchronize. Then, open iTunes’ iPod Preferences panel, deselect “Display album artwork on your iPod,” and allow the iPod to synchronize.
Then, re-enable the preference and sync again. This will force iTunes to recreate the special database of iPod-sized album artwork images, and should clear up any problems you were having..