Deleting songs from your iTunes library is usually very easy. You can either select a song, Control-Click on it and then select “Delete”, or you can simply press Delete from the keyboard, and iTunes will bring up a little window asking if you are sure that you “want to remove the selected song from your iTunes library.” (Seen below.) Select “Remove,” and iTunes brings up another window asking if you want to keep the file in the iTunes Music folder or to move it to the trash. Answer iTunes, and you are done deleting the song from your iTunes Music library. However, this method only works while browsing within the main iTunes library, and not while viewing a song from within a playlist.
Following the first steps of removing a song from your iTunes library while in a playlist leads to a prompt that asks if you want to remove the song from the playlist, not the library. (Seen below.) In order to actually remove the song from the entire library while viewing it from the playlist, press Option-Delete instead of just Delete, and you will get the same prompt as from before in the library! (Seen above.)
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