The 1935 film Rose of the Rancho introduced the standard “If I Should Lose You.” The romantic comedy about early Spanish settlers in California starred John Boles and Metropolitan Opera star Gladys Swarthout in her film debut. The film was adapted from a successful Broadway show by David Belasco and Richard Walton Tully. In his book Hollywood Musicals Clive Hirschhorn describes the movie as an “uneasy mix of operetta and low comedy.” Swarthout plays a dual role as a demure senorita who by night disguises herself as the notorious bandit, Don Carlos, and leads a group of vigilantes. Although accounts of the film differ, it appears that she was the singer who introduced “If I Should Lose You.”

The score was by composer Ralph Rainger and lyricist Leo Robin who had teamed up in 1931 and contributed many popular songs to films in the ensuing decade. However, this particular score was not memorable, and even “If I Should Lose You” didn’t catch on immediately. It was recorded in 1936 by Richard Himber and His Orchestra, a popular radio band, with vocalist Stuart Allen and rose to number 15 on the charts.

Alec Wilder in his book American Popular Song: The Great Innovators, 1900-1950 calls it “a very good song” and an “illustration of safe gloom,” describing its harmonic direction as “interesting.”

In 1949 jazz visionary Norman Granz recorded alto saxophonist Charlie Parker playing an album of all standards accompanied by strings arranged by Jimmy Carroll. The appeal of the album, the first to pair a jazz soloist with strings, prompted subsequent recordings with the same format. It was Parker’s version of “If I Should Lose You” that brought the song to the attention of both jazz instrumentalists and vocalists such as pianist George Shearing (Black Satin), and vocalists Frank Sinatra (Live in Australia 1959) and Nina Simone (Wild Is the Wind). It was also recorded by pianists Hank Mobley and Mulgrew Miller and vocalists Carmen McRae and Jimmy Scott. Contemporary instrumentalists and vocalists such as soprano saxophonist Jane Ira Bloom, singer/pianist Dena DeRose, and guitarist Philip Catherine continue to explore the song in fresh interpretations.