Bobby Darin Sings The Shadow of Your Smile is a studio album by the American singer Bobby Darin, released in April 1966. The album was arranged and conducted by Richard Wess (who conducted Darin's earlier albums, That's All, and This is Darin, and From Hello Dolly to Goodbye Charlie, and Shorty Rogers. It included all the Oscar-nominated songs from 1966. It was his first album on the Atlantic label after leaving Capitol Records.