"The Shadow of Your Smile" is a 1965 Academy Award winning song from the film The Sandpiper.

The Shadow of Your Smile may also refer to: The Shadow of Your Smile (Astrud Gilberto album) (1965) The Shadow of Your Smile (Johnny Mathis album) (1966) The Shadow of Your Smile (Andy Williams album) (1966) The Shadow of Your Smile (Friends of Dean Martinez album) (1995) Bobby Darin Sings The Shadow of Your Smile (1966)