First performed by Ethel Waters (1940).
First commercial recording by Ella Fitzgerald (1940).
Popular versions by Helen Forrest (US #1 1943), Ethel Waters (1946), Frank Sinatra (1954), Anita O’Day (1957).
Also recorded by Dinah Shore (1958), Liza Minnelli (1977).
From the wiki: “‘Taking a Chance on Love’ was written by Vernon Duke with lyrics by John La Touche and Ted Fetter, and has gone on to become a standard recorded by many artists. It was first performed in the Broadway musical Cabin in the Sky which opened at the Martin Beck Theater on October 25, 1940. (‘Taking a Chance on Love’ was added only three days before the New York opening, but it turned into the hit of the show.)
“The show was choreographed by George Balanchine and was a ground-breaking musical with an all-black cast. The leads were played by Ethel Waters as Petunia, Dooley Wilson (‘As Time Goes By‘) 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, and would reprise her performance in the 1943 motion picture release of Cabin in the Sky.
“Ella Fitzgerald recorded the first commercial release of the song in 1940. A Benny Goodman cover featuring Helen Forrest (which was also recorded in 1940) reached #1 on the ‘Hit Parade’ in 1943 after the filmed release of Cabin in the Sky. Ethel Waters re-recorded the song for commercial release in 1946. Other popular versions of ‘Taking a Chance on Love’ were later recorded by Frank Sinatra (1954) and Anita O’Day with the Oscar Peterson Quartet (1957).
“Beside its appearance in Cabin in the Sky, ‘Taking a Chance on Love’ has also been used in Remains to Be Seen (1953), This Could Be the Night (1957), and New York, New York (1977, performed by Liza Minnelli).”
Ella Fitzgerald, “Taking a Chance on Love” (1940):
Helen Forrest with The Benny Goodman Orchestra, “Taking a Chance on Love” (1943):
Ethel Waters, “Taking a Chance on Love” (1946):
Frank Sinatra, “Taking a Chance on Love” (1954):
Anita O’Day, “Taking a Chance on Love” (1957):
Dinah Shore, “Taking a Chance on Love” (1958):
Liza Minnelli, medley from New York, New York (1977):