Getting a song out of a playlist is simple enough. Just right-click it, and choose Delete from the floating menu. (Or, select it and push the DEL key.)But if you then search for the song you “deleted,” you’ll discover that you still have it!
That’s because a playlist is just a list of pointers to songs that are stored in “Songs.” All you really deleted was a playlist pointer, a tiny piece of data. That’s fine if you want to keep the song in other playlists, or if you just like having it around even tho it’s not on any playlist.
If you want to free up the storage space occupied by the song, you’ll have to work a little harder. What to do:
Display the song in “Songs.” A fast way to do this is to search for the song; then click on the song in the search results. (Clicking on “Show <song> in Purchased” does no good; “Purchased” is just another playlist.) If you were using the sidebar, you’ll notice that it goes away; and the iTunes selector bar on the top edge of the display switches to “Songs.”
Right-click the bad song in “Songs,” and choose Delete from the floating menu. This time iTunes will ask “Are you sure you want to delete this copy of the selected song?” Check “Also hide this song in iCloud.” Click Delete song.There’s still one more place to clean out. Notice that “Keep file” is the default; don’t take it. Instead, click Move to trash.Test that the song is really deleted from all of the compartments of iTunes by searching for it again. If iTunes invites you to search the iTunes Store, you’ve gotten it.
Alert reader Raspberrypihtpc advises;
This process only works for files that are inside of the “iTunes Music” folder.
The iTunes Music folder is automatically used for imported music, and if “Keep iTunes Media folder organized” is checked off.
If you have music in other folders, the process is more complicated (and manual-labour intensive)