Until I need a new iPod, I will stick with my 5th-generation video iPod and it’s 60GB space limitations. This means, for instance, that come Christmas time I have to de-sync a lot of albums from the iPod to put Christmas music on the iPod. And on the long drive home to my parents for Christmas, Marlin and I discovered my album covers on the iPod were sometimes wrong. We were listening to Crosby Stills and Nash “Daylight Again” album, but the iPod was sometimes displaying the Thompson Twins. So I played a game for a little while, bouncing around on the iPod. Thompson Twins “Greatest Hits” sometimes had the album cover for Jet (the band made famous by the iPod commercials, not the Paul McCartney album). Jet sometimes displayed a Morrissey album cover. And so on. It was as if some iPod gremlin shuffled the album covers.
I couldn’t find any solutions at Apple’s web site, but a web search eventually uncovered this post at fonzo.biz: iPod Nano Artwork – Fixed
The posted fix is a couple years old, so apparently this problem has been around for a while, and a scan of the comments seems to indicate that moving large numbers of albums onto and off the iPod triggers the album cover shuffle. The post is also outdated for newer versions of iTunes where the option to enable/disable album artwork display on iPod is now on the Music tab for the device, and not in the Preferences section of iTunes.
As far as I can tell, the fix worked fine for me, but it took a long time re-syncing the album covers. Long as in a few hours.