Your selection should turn blue.
 This key should be located right next to your Spacebar. Either one will work.
 Make sure that you are still holding down Ctrl or ⌘ Command. Don't let go of it until you're done selecting all the songs you want.
 You can scroll up or down within iTunes to find other songs without losing your selection.


You can let go of Ctrl or ⌘ Command without losing your selection. Just make sure you press down on it again before clicking another song. Otherwise, you'll lose the whole lot.
If you tend to have trouble with this process, it's probably safer to just keep holding down Ctrl or ⌘ Command.
Click the first song you want.
Hold down Ctrl (PC) or ⌘ Command (Mac).
Click on the next song you want.
Continue clicking other songs.
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