What follows is a survey of some good and bad guesses made by the iTunes Store’s new “get missing cover art” feature.

Granted, iTunes 7 has its other oddities, like the new use of BOLD CAPS as section headers in the store and various other parts of the interface. Are people at Apple prone to SHOUTING all of a sudden? “Hey, Jennifer, there are no good PODCASTS in your LIBRARY. Let’s go to the STORE and get some audio for your DEVICES!”

But what surprised me is when I started using iTunes to fill in some missing cover art that I hadn’t yet filled in with images.google.com searches. Scot has already pointed out many of the changes in cover art handling. My topic here is that the cover art search can produce curious results. The first sign that this was an process replete with some hazards is when I got the cover art for Todd Rundgren’s 1990 album, Nearly Human.

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You see, the problem is, that’s not the cover to Nearly Human. This is:

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What iTunes found with that search was
Todd Rundgren - Bootleg Series, Vol. 3: Todd Rundgren - Nearly Human Tour Japan '90 [iTunes link], a CD from the subsequent tour (as for the “bootleg” moniker: Rundgren, like Frank Zappa before him, grabs bootlegs, cleans them up, and releases them under his own imprint so he gets the money from his own work).

The close-but-no-cigar search result speaks to some fuzziness in how iTunes conducts its search. It probably has to be a little fuzzy, because the CDDB, from which most iTunes users will get track names for their ripped CD’s, is a completely different database than iTunes, and with no universal system of identifying CD’s (and MP3’s or AAC’s ripped from them), matches are surely an inexact science.

The first squishy bit of iTunes cover art searching is the issue of just what albums are available at all from the store. A disowned and controversial curiosity out of print for 15 years is surely not going to be found:

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But you’d think a major label release by a major artist from just 10 years ago would be in, right? Wrong:

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In fact, you’re better off with scrappy indie-label ska punk bands from the mid-90’s:

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Then there’s the reissue issue. For example, I got cover art for the soundtrack from Escape from New York:

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But that’s not what my CD looks like! My CD is an old Varese Sarabande release, which looks like this:

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It turns out that the soundtrack has gotten a big re-release on another label, nearly doubling its length. Heck, I might go get the new version, so I put the correct cover art on this rip.

And going back to the mid-90’s, why wouldn’t one of its defining discs be found?

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Ah, but it does. This is a tricky situation, caused by the CDDB. Take a look at how disc 1 of Mellon Collie and the Infinite Sadness is labelled by CDDB:

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That’s right - whoever entered it into CDDB kept the curious subtitles “Dawn to Dusk” and “Twilight to Starlight” Hilariously, iTunes, which equated Nearly Human with Bootleg Series, Vol. 3: Todd Rundgren - Nearly Human Tour Japan '90 does not match Mellon Collie and the Infinite Sadness - Dawn to Dusk to Mellon Collie and the Infinite Sadness.

Fortunately, an easy fix. To unify the two discs of Mellon Collie, you just go into “Get Info” and give them the same title: Mellon Collie and the Infinite Sadness. Be sure to set the “disc X of Y” items correctly for each disc in a collection, so iTunes will play them in the proper order.

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Now ask iTunes for cover art and it should work:

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The other thing that surprised me in iTunes 7 is the disappearance of the “import” button at the upper right:

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I resorted to dragging the track list from the CD to the library to do an import:

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…until I discovered the import button had simply moved to the bottom right, next to the eject button.

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