"The Shadow of Your Smile" is a legendary jazz standard composed by Johnny Mandel with lyrics by Paul Francis Webster.

It won the 1965 Academy Award for Best Original Song and the 1966 Grammy Award for Song of the Year,

It was famously popularized by Tony Bennett's version.

The song was originally introduced as the love theme for the 1965 film The Sandpiper, starring Elizabeth Taylor and Richard Burton.

Johnny Mandel wrote the melody, and lyricist Paul Francis Webster penned the words after the music had been composed

It is one of the rare songs (20) to win both an Oscar and a Grammy.

While Tony Bennett had a minor hit with it, and is most closely associated with the tune, it has been recorded by hundreds of artists, including Frank Sinatra, Peggy Lee, and Astrud Gilberto

The lyrics revolve around the lingering, nostalgic memory of a loved one.

The narrator reflects on how the "shadow" (memory) of a smile will continue to color their dreams and light up the dawn long after the person has gone