I have album artwork for practically every CD that I have ripped. When I transfer my ripped files to iTunes, I want it to bring the album artwork along with it. The online manual doesn’t mention this (or I haven’t found it) but says to manually select songs and specify the artwork yourself. This is madness. I have way too much music and precious little time to do this by hand. Is what I want to do possible?
There’s a setting in iTunes to download the album artwork automatically. It’s one of the options when you set up the program. Just enable it and you’re set (unless, like me, you have a lot of obscure albums with no album art on file).
You can often find very obscure album art online. You may have to settle for smaller or lower-quality images, but I was able even to find Myshkin Impossible for my library.
Of course you can always scan it yourself. 
Ok, I enabled automatic downloading.
Now, just to be clear, iTunes and iPod neophyte that I am, if I now transfer my music, where each artist folder has both music and artwork, to iTunes, I am all set?
Album artwork can be stored in a few places. It can be stored as metadata within the MP3 file itself or within the iTunes database. Artwork stored just in the iTunes database will be transferred to other iTunes devices but won’t go with the MP3 to other devices.
You can force iTunes to write the album art to the MP3 file by right clicking on the file and selecting “Get Info”->“Artwork” and then pasting the album art.
You can also have Windows Media Player automatically update the artwork.
Wait a minute, though. I’ve already got the artwork, I don’t need to download it. I simply want my already existing artwork to be carried along with the tunes when I transfer my music from my hard drive to iTunes.
Assuming you’re using the cover art for the album, what’s the difference?
Not the music I’m listening to. How about “Encores by Joan”? “Head Full of Blues” by L.B. Walker? Live Grateful Dead concerts on archive.org? Other live concerts – Warren Zevon, Little Feat? Various public domain blues MP3s? “The Furry Eggs” (Glass harmonica)?
Only about 2/3rds of the music on my iTunes has an album cover, since much either was never released on an album, or is too obscure to be in a database.
I could bore you with my misunderstandings and/or misconceptions about how I thought this whole thing would work, again, being a neophyte when it comes to iTunes. I won’t. But I will say, that setting that option for automatic downloads solved my problem, as I know you knew it would.
Thanks so much!!
Well yes. Of course you need to have the artwork to start with. But I think the OP was asking how to copy it between devices.