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Adding artwork to multiple songs in iTunes 10

iTunes 10 has a cool new feature that allows you to create a Smart Playlist based on whether or not your music has artwork. To use it, simply set "Has Artwork" to "is false" when creating the playlist. You can (optionally) add "Media Kind: is Music" if you want to avoid seeing podcasts, movies, and other items that don't have artwork.

I recently decided to clean up my iTunes library. This involved taking all of the music out of the iTunes library and only adding back music that I knew I really liked. I was also making sure the metadata was accurate, including the artwork. I had been adding the artwork via TidySongs, but it had been acting a bit unreliably and claiming that iTunes was not responding (the developers tell me there is a new version available for Windows and a new Mac version is due "soon"). So, I started adding artwork manually.

Something very strange has happened that I can't completely explain, so I'll just describe it. I've found songs in my "No Artwork" playlist that had artwork (clearly visible when using Cover Flow), but if I examine the song individually using the inspector, the artwork is indeed missing. I'm not sure how this is happening, but I have noticed a pattern that might give a clue: all of the "phantom" artwork was added by dragging manually to the "Drag Artwork Here" area on the bottom left of the iTunes window while multiple songs from the same album were selected. If I examine the files in the Finder, some of them have the artwork, and some of them don't.

Why is this happening? I have no idea. Frankly it makes no sense, and I suspect that there's a bug in there somewhere. (Or maybe that fortuneteller actually did put a curse on me.) Whatever the reason, there does seem to be a workaround.

  1. Select all of the songs that you want to apply the artwork to
  2. Use command+i to call up the inspector
  3. Drag the artwork to the inspector instead of the "Drag Artwork Here" area

I don't know why, but that method has worked 100% reliably for me without leaving any "stragglers" lacking artwork. It's a bit of a hassle, but that's a trade-off I'll take for something that works better.

Thanks to Guillermo Esteves for drawing my attention to the new iTunes feature.

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