I really regret not taking a picture of this when it happened, but recently I added an album to my ipod (The very best of Elvis Costello) and after doing so, every album inherited the Elvis cover art. Now this particular album does not have the most flattering picture of EC, so I was interested in correcting this problem. When I looked in iTunes, everything was normal there, so I tried to sort it out myself. After a little trial and error, I noticed that if I did the following, I could correct the problem:
* view the ipod-bound playlist
* sort by album view
* Get info on the first (or any) track, select the Artwork tab (iTunes remembers your selection for next time)
* Select the artwork (click on it) and then copy it to the clipboard (press CTRL-C in windows)
* Return to the Album view and select all of the tracks in the album you just grabbed artwork for
* Right click and choose Get Info again - this time it is for the group of tracks which brings up a different screen.
* Click on the Artwork input box and paste the art into it (CTRL-V to paste in Windows)
* When you click the OK button from here, iTunes will reprocess these songs and the next time you sync, this album art will appear correctly on the ipod.
I had to do this for each album, so I also took some time to clean up the files a bit - for example, my Elvis Costello collection came in as separate albums for most of the tracks because it is a compilation album spanning most of his work. By providing too much detail such as the album a song was originally released on, iTunes thought it was best to separate these into different albums. By making the Artist and Album fields consistent (and blanking out the Album Artist field) these tracks finally appeared as a single album and not as a dozen or so.
My music collection is not all that large, so this was a workable solution for me. If someone had hundreds of albums, I could see this being a chore too big to handle in this way, and in fact, there very well may be a simpler solution. This worked for me and only took me about half an hour to complete.
UPDATE: It really bugged me not having a photo of the display problem, so here is a photo of what it looks like after I corrected things.
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