"The Shadow of Your Smile", also known as "Love Theme from The Sandpiper", is a 1965 song with music by Johnny Mandel and lyrics by Paul Francis Webster. It was written for the film The Sandpiper (1965). Mandel's first choice for the lyrics was Johnny Mercer, but the film's producer hired Webster instead. In the film, the melody was first heard as an instrumental over the opening credits, played by jazz trumpeter Jack Sheldon, and a chorus sang it over the closing credits. Robert Armbruster conducted the film music, which was produced by Quincy Jones.
The song won the Academy Award for Best Original Song and the Grammy Award for Song of the Year, the latter for Tony Bennett's 1965 recording, arranged and conducted by Mandel and released on The Movie Song Album in 1966. Bennett's version reached No. 28 on Billboard's Easy Listening chart and No. 95 on the Hot 100. Today it is a popular song and jazz standard, part of the Great American Songbook, recorded by Peggy Lee, Astrud Gilberto, Barbra Streisand, Johnny Mathis, Sarah Vaughan, Marvin Gaye and many others.