Tonight I Shall Sleep with a Smile on My Face is a Duke Ellington composition with lyrics by Irving Gordon and Mercer Ellington. The tune was first recorded and released by Tommy Dorsey with Duke Ellington and His Famous Orchestra in 1945, after being recorded on May 14, 1945 and released on June 4, 1945. Published June 14, 1943, this English language big band vocal ballad sits in the swing era repertoire. It is commonly regarded as jazz and big band music, known for its moody lyricism and lush orchestration. The song has many versions and covers, including a 1949 rendering by Sarah Vaughan and a later appearance on her Duke Ellington Songbook Vol. 2 (Remastered, 1979). Other notable interpreters span Stan Getz, Zoot Sims and many others, making it a widely performed jazz standard. The lyrics explore inner conflict and longing in a nocturnal setting, balancing primal emotion with tenderness.