If your iTunes music library is your one-stop shop for all things audio, then it's probably time to start adding iTunes artwork to liven it up.
Cover Flow gives your iTunes music a slick look, but it's only really worth it if you can actually see the album artwork that goes with the music. Besides, wouldn't it be better to listen to Michael Jackson's Thriller 25th anniversary or Justin Timberlake's latest with their album covers flowing across the screen?
If you buy your music on iTunes, you already get the artwork, but for all those CDs you've ripped or for all those tracks you got from other sources, the artwork may not be there. Getting it isn't all that difficult, and the process can be fun, even if it is a little time-consuming.
Try Getting Artwork through iTunes
By now, you've probably upgraded to the latest version of iTunes, especially since Apple never fails to remind you when it's ready for download. If you have, you might not know it but there's a built-in feature that automatically downloads any album artwork to your iTunes music library, provided that Apple has it in its iTunes Store.
Just go to the "Advanced" tab on the menu and highlight "Get Album Artwork" to have the software pick up whatever it can. It's pretty good, but it's definitely not an exact science. You'll find that there are still plenty of songs that are stuck with that empty grey box when shuffling through your playlists.
You'll also probably find some songs that have the wrong Greatest Hits artwork, or even the wrong artist altogether. This happened to me when my Scarface movie soundtrack ended up with artwork from the rapper of the same name.
You should also know that when grabbing artwork this way, it sticks with iTunes, so you wouldn't be able to transfer it all to another music player (that isn't an iPod), or even share it with friends. If that's no big deal for you, great, but if it is, skip this step and move on to the next one.
Try Finding Artwork Online
There are some websites and software apps available online that are purely meant to grab artwork for iTunes music libraries. The most popular one is Art4iTunes, which matches album covers from Amazon.com and latches them onto your music files. That means they're for keeps, so if you copy/backup your MP3s, or even just start using a different music player, the artwork goes wherever the music goes.
Highlight all the songs in your collection, go to File on the menu bar, and choose "Export." Here, you can just save it as a regular text file onto your desktop. Go to the Art4itunes website and upload that text file. At this point, you'll need to have the site and iTunes side-by-side on your computer screen so you can drag and drop the images into the window at the bottom left of iTunes where it says "Drag Album Artwork Here". If you don't see that window, go to View on the menu and choose "Show Artwork" to have it pop up (Ctrl + G on a PC, ⌘ + G on a Mac).
Now it's just an exercise of dragging the right image into that box for each album or artist.
Picking Up the Stragglers
It's very likely that you'll have some slots left to fill, no matter which of the previous two options you decided to go with. You can start searching for stragglers through Google Images, Buy.com, Discogs.com or even Wikipedia. Ideally, you want the images to be a decent size to fill in the whole image box in Cover Flow, so try to find ones that are of equal size when you view them.
When you find a winner, just drag it over to the empty image box and you're good to go. In the event that you somehow got the wrong image into the box, don't despair. Highlight the track you want to change and press Ctrl + I (or ⌘ + I on a Mac) or right-click on the track and choose "Get Info". Here, you'll see all the details about the track, including any images attached to it. Delete the image you don't want and drag in the one you do, and that's it.
Plug in Your iPod or iPhone
It's great to have all that album art on iTunes, but you also want to enjoy it on your iPod or iPhone, so plug it in and let it sync everything over. If you're using a different music player, and you manually filled in the image slots, then the artwork should show up with the music. Of course, that's assuming there aren't some DRM restrictions attached to your tracks.
When that's all said and done, you should be covered on both your computer and music player — viewing actual images rather than empty boxes.