Delete a song in an iTunes playlist, and physically remove it from the hard disk

Posted by David Chin on June 10th, 2008 in Music, Shortcuts

Here’s the story.

I’m on a MacBook Pro 2.4 GHz, and I launch iTunes.

I create a smart playlist, called “To delete”, in iTunes to collect all songs with a 1-star rating.

My intention is to physically obliterate these songs from my hard disk - I don’t ever want to see them again, not in this lifetime anyway.

I just want to free up some HD space, and moving these unwanted songs into the Trash is taking the first step.

I navigate to the smart playlist.

I then highlight all the songs (and there’s a whole bunch of them).

I then tried pressing command + delete - nothing happens.

I tried alt (option) + delete - I only get the option to remove the selected songs from the iTunes library. Not good, as these songs will still be taking up hard disk space, but won’t appear in iTunes.
iTunes option to remove selected songs from the library

After a bit of searching, it turns out that I need to perform a finger-twisting shift + alt (option) + command + delete so that I get the prompt to remove these tunes from iTunes and move them to the Trash.
iTunes option to move files in a playlist to the Trash

I’ll leave it to you to decide which finger goes to which key. You don’t have a choice, as even the option to delete selected songs on the menu is grayed out when you’re in a playlist.
iTunes option to delete a song from the playlist is grayed out

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