Richard Rodgers composed "Little Girl Blue" with lyricist Lorenz Hart for the 1935 Broadway musical Jumbo, a lavish circus-themed spectacle produced by Billy Rose at the Hippodrome Theatre that was the most expensive Broadway production of its era. Gloria Grafton introduced the song in her role as Mickey Considine, singing it amid a plot involving rival circus owners' children falling in love. The tune marked Rodgers and Hart's triumphant return to Broadway after a period working in Hollywood. Musically, it is a tender ballad in F major with an unusual structure: two 12-measure A sections followed by an 8-measure trio that shifts to three-quarter time, giving the song an asymmetric shape uncommon among standards. Rodgers employs his characteristic device of repeating the same note before descending stepwise, while Hart's lyrics move from the prosaic ("Sit there and count your fingers") to the poetic ("count the raindrops falling on you"). Theater restrictions initially delayed its wider popularity, but Margaret Whiting brought it to the pop charts in 1947. Nina Simone's 1958 debut album took the song as its title and featured a celebrated interpretation that interpolated the medieval carol "Good King Wenceslas" as a piano countermelody. Frank Sinatra recorded it with Nelson Riddle in 1953, and notable instrumental treatments include Jimmy Smith's 1957 organ trio version with Kenny Burrell.