Q: How would one create a playlist and associate a unique piece of artwork with it? What I want to do is to create a playlist which corresponds to a compilation album (which I don’t own), from tracks that come from individual albums (which I do own), and associate the compilation album’s artwork with the playlist. Unless I’m mistaken, the only way to do it is to create duplicate copies of the desired songs in my library and tweak their metadata to make them look like they came from the compilation, which is not what I want to do. Any suggestions?
A: Unfortunately you are correct that this is not possible. iTunes and the iPod media devices are entirely tag-based and take the album artwork from the tag of the current track being played. This allows you to potentially choose unique artwork for each track, however each track only gets one piece of artwork that can be displayed (iTunes will allow you to add multiple artwork images to a track, but only the first one gets shown).
The only workaround is the one you’ve already suggested—duplicate the tracks and change the album and artwork tags to reflect the compilation album. Unfortunately, this not only means that these tracks will take up additional space in your library, but any rating and play count metadata will be tracked separately.