I Guess I'll Hang My Tears Out to Dry

Originally written for the 1944 Broadway show Glad to See You, which closed out of town before reaching New York, this torch song survived the failure of the show to become one of Cahn’s most enduring standards. Sinatra’s 1958 recording for Frank Sinatra Sings for Only the Lonely is considered definitive — a masterclass in late-night heartbreak.

Chet Baker and Diana Krall both found it irresistible, and it remains a go-to for jazz vocalists drawn to Cahn’s gift for articulating quiet devastation.