The tune was named after Rubie Richardson, Monk's first love and his older sister Marion's best friend. It was first recorded at a 1947 session for Blue Note Records. Monk recorded "Ruby My Dear" several times, including solo piano performances in 1959 and 1965, as well as versions with saxophonists Coleman Hawkins and John Coltrane (at New York's Five Spot Jazz Cafe in the summer of 1957). Lyrics were written by Sally Swisher and the song was recorded in 1988 by Carmen McRae as part of the studio album Carmen Sings Monk. For copyright reasons, the song was renamed Dear Ruby.