The Broadway musical Cabin in the Sky opened at the Martin Beck Theater on October 25, 1940, and ran for 156 performances. It was choreographed by George Balanchine and performed by an all-black cast. The leads were played by Ethel Waters as Petunia, Dooley Wilson as her husband Little Joe, and Katherine Dunham as the temptress Georgia Brown. Waters introduced “Taking a Chance of Love” as a show-stopping solo, reprising it at the end of Act I with Little Joe. Despite the fact that the song never made it to the popular radio show Your Hit Parade, according to Allen Forte in The American Popular Ballad of the Golden Era, 1924-1950: A Study in Musical Design, big band performances and recordings of the song made it a standard.

The composer was Vernon Duke and the lyricist John Latouche. Ted Fetter is often credited as co-lyricist, but in fact he had written an earlier lyric for this song which Duke had dug out of the proverbial trunk and for which Latouche supplied a new lyric. In his book The American Musical Theatre Song Encyclopedia, Thomas S. Hischak says, “[Duke] and lyricist Ted Fetter had written a number called ‘Fooling Around with Love’ years before, but for the ‘Negro fable’ Cabin in the Sky lyricist John Latouche revised it into the sterling song known today. The new number was added only three days before the New York opening, but it turned into the hit of the show.”

The plot, based on a folklike play by Lynn Root, is a takeoff on the Faust legend. The philandering gambler Little Joe, loved by his forgiving wife Petunia, is shot and killed but given another chance to redeem himself on earth where he faces the temptations of femme fatale Georgia Brown.

The Benny Goodman Orchestra recorded “Taking a Chance on Love” in 1940 with Cootie Williams on trumpet and Helen Forrest on the vocal. However, it wasn’t until the release of the film version of Cabin in the Sky in 1943 that the Goodman rendition charted for 14 weeks, three of them in the number one spot. Sammy Kaye and His Orchestra also recorded the song in 1940, and their version hit the charts in 1943 for two weeks, peaking at number 13.

Despite the obvious talent of the all-black cast and praise for Duke’s score, many critics point out the racial stereotypes perpetuated in the show. What may not have been so offensive to audiences in the ‘40s strikes home all too clearly in modern times. Ken Mandelbaum, in an online article at Broadway.com, says that “...similar questions had been raised about the property when MGM purchased the film rights to the Broadway show.” To allay concerns from the black community, “...MGM producer Arthur Freed issued a statement: ‘More than ever before we are aware of the Negro problem and are daily moving toward a better understanding. One that in the end will result in a dignified presentation of a peace-loving and loyal people.’”

Waters reprised her role as Petunia in the film, Eddie “Rochester” Anderson played Little Joe, and Lena Horne played Georgia Brown. Louis Armstrong had a small role as a trumpeter and the Duke Ellington Orchestra was featured on camera. Only the title song, “Honey in the Honeycomb,” and “Taking a Chance on Love” were retained from the original show. Seven numbers were added to the film, and one of them, “Happiness Is Just a Thing Called Joe” by Harold Arlen and Yip Harburg, was sung by Waters and nominated for a Best Original Song Oscar. Despite favorable reviews of the film, many theaters in the south refused to show the picture.

In 1964 Cabin in the Sky was revived as an Off-Broadway production. Although it ran for only 42 performances it produced a well-received cast album under the auspices of conductor/arranger Sy Oliver. The show included a song cut from the original show, a new song written by Vernon Duke, and a song interpolated from another Duke musical. None of the Arlen/Harburg songs from the film were included in the revival.

Vocalist Jane Monheit’s 2004 CD release Taking a Chance on Love rose to number one on Billboard’s jazz chart and climbed to the top 100 on the pop chart. Lester Young recorded the song with Teddy Wilson’s quartet. The Dave Brubeck Quartet and pianist Jessica Williams have performed it as well as guitarist Tal Farlow, trumpeter Wynton Marsalis, and saxophonist Joshua Redman. Since 2000 it has been recorded by pianist Marc Copland, vocalist Nancy Wilson, guitarist Martin Taylor, and pop idol Rod Stewart. Vocalist Sara Lazarus recorded it in 2007, and trumpeter Terell Stafford included it in his 2007 release Taking Chances.