Ask the iTunes Guy: Issues with managing iTunes files

Got questions about iTunes? Kirk McElhearn has answers.

The iTunes Guy

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I’ve gotten lots of interesting questions lately, many of which go deep into how iTunes manages files. The first one I look at asks about double entries for songs in iTunes. I also look at a possible way that Apple could add new, interesting smart playlist conditions, and I discuss holiday music, which you really don’t want to hear all year round.


Q: I moved some of my music files from the iTunes Media folder to an external hard drive. The tracks remained visible in iTunes, but unplayable (clicking on them prompted a dialog box asking to locate the tracks). I re-added the music files to my iTunes library, but now every track is listed twice. If I delete one of the listed tracks, the associated file gets deleted. How can I get rid of these double entries?

You’ve found one of the keys to maintaining a healthy iTunes library: never move files on their own. iTunes is a database that keeps records of where your files are located, and if you move them, iTunes doesn’t know where you’ve put them. Adding them back added another copy of each track, but iTunes was smart enough to know that the original tracks were in that location, so it set the location to the same file for both entries for each track. Deleting either of the entries deletes that file, but not the second entry for a track.

To prevent this in the future, put all the tracks you plan to move in a playlist. Move them in the Finder, if you must, then delete them from the playlist. When you re-add them, you’ll only have one entry for each track. But it’s best to not make this type of move at all; if you run out of space, either move your entire library to a larger hard drive, or use TuneSpan, which can move some of your media files to a different disk.

To fix your problem, you can use Doug Adams’ Scan for Double Entries AppleScript. Read this blog post explaining how it works, and download the script here.

No repeats

Q: I’d like to create a smart playlist to do the following: a) Not repeat a song within a certain number of months, and b) not repeat an artist within, say, a few days, or maybe until, say, 25 songs by other artists get played. The first part is easy, but is there any way to get the second part to work?

As you say, the first part is easy. You set a condition in a smart playlist where Last played not in the last 3 months.

last 3 months

You can set a condition in a smart playlist to not repeat music you’ve heard in the last few days, weeks, or months.

However, there’s no way to accomplish the second condition. I often get questions about this; people want to not hear back-to-back songs by the same artist, or not hear the same artist more than once in 10, 20, or 50 songs. It would be great if Apple could add this sort of condition, and I can think of one way they could do so.

If you have a Recently Played smart playlist, you’ll see the most recent tracks you’ve listened to. If you were to limit that playlist to, say, 25 tracks, you could exclude tracks using that playlist as a condition. (Playlist is not Recently Played.) To exclude an artist, you would need to be able to use a condition such as Artist is not in Playlist Recently Played. So you would leverage the Recently Played smart playlist, and be able to exclude any track from an album, artist, genre, etc., which is in that playlist. You could limit the playlist to any number of tracks, so if you wanted to not hear the same artist for 10 tracks, you set your Recently Played playlist to only show 10 tracks. If you want that limit to be 50 tracks, you set the playlist to display that many tracks.


Q: Is there a way to hide a genre? We have a large library of Christmas music that we listen to from after Thanksgiving until early January. The rest of the year we don’t want to see it.

You can’t hide a genre, alas. I get this question a lot, specifically about holiday music. You could remove this music from your library entirely, store it in a folder, and add it back when the holiday season comes around, but doing this would lose any ratings or play counts, and also remove the tracks from any manual playlists you’ve created.

If you want to do this, the easiest way is to create a smart playlist with the condition Genre is Holiday (or whatever you use as the genre for this music). Go to the Finder, and create a new folder; call it Holiday Music. Open that folder. Back in iTunes, select all the tracks from the smart playlist, and drag them to the folder’s open window in the Finder. iTunes will copy all the original files. Next, back in iTunes, delete all the files from the smart playlist; press Command-Option-Delete to do this.

When the holiday season comes around again, just drag that folder back to iTunes window to add the files.

Personally, I’d leave them in iTunes; there’s more of a risk of losing files when you shunt them in and out of the iTunes library. If you want to make sure they don’t get played in shuffle mode, use the smart playlist I suggested above, select all the tracks, right-click, and then choose Uncheck Selection. iTunes doesn’t play tracks that are unchecked when in shuffle mode or if the tracks are in playlists. (You can still play a single track if you double-click it.) Next Thanksgiving, select the tracks, right click, and choose Check Selection and you’ll be able to play them again.

Have questions of your own for the iTunes Guy? Send them along for his consideration.

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