Bet You Didn’t Know: Secrets Behind the Making of “Lady Sings the Blues”

April 15, 2014  |  
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The Back Story w/ Jay Weston

Lady Sings the Blues is one of the most critically acclaimed black films and biopics of all time — with five Academy-Award nominations. But have you ever wondered the back story of the successful film about Billie Holiday’s life and career? We got you!

Jay Weston is the man who started it all. Intrigued by Holiday’s life and telling her story,  he, at the time in 1959, was an aspiring movie producer and told Holiday’s agent, Joe Glaser, he wanted to make a film about her life after reading her autobiography. He payed her agent $5,000 a year to the have the option to make the film until 12 years later when the movie was finally made.

Below is a photo from Weston’s Huffington Post back story about the film. But in each slide we break down the story behind the scenes and what it took to make this musical biopic.

Berry Gordy

Jay Weston took interest in Ross playing Holiday after seeing Ross in Look Magazine, revealing she wanted to play Holiday in a movie. But Berry Gordy, her manager and founder of Motown, wasn’t having it. He didn’t think she should play a black junkie singer. He rejected the idea twice.

Diana Ross

But Ms. Ross is a boss and she demanded Gordy let her play the role of Billie Holiday . After Gordy had a meeting with the movie’s players, he finally agreed to let Ross do the movie if it was done by a major studio.

Though Ross was sure she’d win the Best Supporting Actor Academy Award after being nominated, the honor actually went to Liza Minelli for her part in Cabaret. Weston said Gordy allegedly overdid the campaigning.

Billy Dee Williams

Williams was spotted by Weston in an off-Broadway production of Slow Dance on the Killing Ground. In the production, Williams played a smooth-talking hustler and afterward Weston set out to find this good-looking actor with no agent or no address to play Holiday’s husband Louis McKay. Randomly, at a supermarket, Weston spotted Williams again in a dashiki and asked him to attend a Hollywood party with the big dogs. Williams did, and although liked, he was deemed too young. Weeks later he grew a mustache and requested a screen test, which he did with Ross. The next day she told Weston he’s the guy.


Foreign Distribution

Gordy took a very active role in the film’s production. He struck a deal with Paramount for the foreign distribution in an exchange for the whole $2.5 million budget. Weston said this was a bad idea looking back since Gordy hired the wrong guy for the foreign distribution and the major studio never saw the international success (like domestic) they would have liked.

Gordy was also said to have assumed the role of producer, due to his major contributions. And the rest of the film’s major players were shut out, like at the Cannes Film Festival in 1972 where Ross performed and the film closed the festival.

Dorothy Dandridge

In an earlier script and proposed version of the biopic, Dandridge was to play Holiday. Unfortunately, tragedy struck as Dandridge died from an overdose in 1965 — six-and-a-half years before the film was released.

Diahann Carroll

At some point and time Carroll was one of the many actresses attached to play the lead. Like the other women on the list who didn’t play Holiday, she went on to receive her own Academy-Award nomination for Best Actress, just two years after the release of this film, for her role as a single working mother of six on welfare who soon meets a true, yet complicated love in Claudine.

Cicely Tyson

And speaking of other actresses up for the role of Holiday while winning their own Academy-Award nominations, Tyson was up for the lead, but although she didn’t land the part she does share history with Ross. They both were nominated for Best Actress at the 1973 Oscars. For the first time in history, two black performers were nominated in the same category, a lead category, and the category for Best Actress. Tyson was nominated for her brilliant role as a Sharecropping mother whose husband (Paul Winfield) is imprisoned for stealing food in Sounder. Winfield was nominated for his role as Best Actor.

Levi Stubbs

Before Billy De Williams took the part of Louis McKay, Motown was going to keep it in the family with Stubbs, who was the lead singer of The Four Tops. Fortunately or Williams, he was on tour with the Tops at the time.

Richard Pryor

Pryor is the man who taught Ross how to pretend  to be a junkie during filming since he had his own issues with drugs before passing away in 2005 from a heart attack. But Pryor wasn’t meant to be a significant character in the film originally. It was his line delivery of “Hey Jerry, give the girl a chance” that made him stand out to the crew. They created an extended role for him known as Piano Man.


Ross sung the original motion picture soundtrack herself and, in return, it became one of the biggest soundtracks ever and definitely one of the quintessential black movie soundtracks. It went number one and became a best seller.

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