How to delete multiple files from your iTunes library.
From Inside iTunes:
Getting rid of duplicate songs in your library.
If you have a large song library, duplicate copies are inevitable. To trim down to only what you want, use the Display Duplicates command in the File menu, then delete the songs you want to get rid of (you'll have the option to remove them from iCloud as well, and to put them in the trash on your computer).
One user suggests the following thread (a snippet below, follow link for more):
iTunes has two modes for displaying duplicates. The first is accessed via File > Display Duplicates and lists all tracks in the current playlist where the same track title occurs more than once. This is, more often than not, a rather loose definition of the term and can bring back obviously different songs, e.g. studio and live versions of the same song, the same song recorded by different artists, or by the same artist but on different albums, or completely different songs that have nothing in common but their title.
A more useful feature can be found if you hold down the SHIFT key and then select File > Display Exact Duplicates. This gives a list of all tracks where more than one track has essentially the same metadata, name, track no., artist, album, etc. (I'm not sure what the exact criteria are for an exact duplicate as far as iTunes is concerned, but it's good enough for most needs).
From Apple Support:
You may sometimes see an item displayed more than once in your iTunes library. To find and remove all items that show up more than once in your library, follow the steps below. (follow link here or above)
From Wideanglesoftware.com:
A third-party app for sale is Tunesweeper.
"Tune Sweeper's unique design makes it simple to browse and safely remove duplicate and missing tracks in your digital music collection. Tune Sweeper will also quickly find tracks on your hard disk that are not currently in your iTunes library."
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