iPod: The Missing Manual (Missing Manuals)

If you want to delete a song or songslike when you outgrow your Britney Spears phase and want to reclaim some hard drive space by dumping those tracks from the OopsI Did It Again albumclick the title in the Albums pane, select the songs you want to delete from the song list, and press Delete (Backspace).

NOTE

Selecting songs works just like selecting files in the Finder. Select a swath of consecutive songs in the list by clicking the first, then Shift-clicking the last. Add or remove single additional songs to the selection by -clicking (Mac) or Ctrl-clicking (Windows).

When iTunes asks if you're sure you want to delete the music, click Yes. You'll usually be asked twice about deleting a song, the first time for deleting it from a list, the second time about deleting the music file from your iTunes music library altogether. If you want your hard drive space back, click Yes to both.