The Shadow of Your Smile, also known as Love Theme from The Sandpiper, is a 1965 song written by Johnny Mandel with lyrics by Paul Francis Webster. It was introduced in the film The Sandpiper in an instrumental version featuring a trumpet solo by Jack Sheldon, and was released on the film’s soundtrack album The Sandpiper. The tune sits in the pop and easy listening realm and later became a vocal standard with many covers, including versions by Tony Bennett and Astrud Gilberto. It won the Academy Award for Best Original Song and the Grammy Award for Song of the Year, and in 2004 it ranked number 77 in AFI’s 100 Years...100 Songs list.