“The Greatest Improviser I’ve Ever Known”: A Mini Oral History of Diana Ross in ‘Lady Sings the Blues’

On Sunday night at the 93rd Academy Awards, when Andra Day is singled out as a best actress nominee for her performance as Billie Holiday in The United States vs. Billie Holiday, veteran Oscar watchers might well experience a moment of déjà vu. Forty-eight years ago, another popular singer, Diana Ross, was sitting in that same seat, having been nominated for her breakthrough portrayal of Holiday in 1972’s Lady Sings the Blues. The film, which earned a total of five nominations, went home empty-handed that night, but it had already left a mark on the popular culture.

In terms of box office rentals, it was the ninth most popular film of ’72, and its double-album soundtrack reached number one on Billboard’s Hot 200 Album Chart. “It was an amazing experience,” recalls Jay Weston, the veteran producer who spent more than a decade trying to put the project together before finally convincing Motown founder Berry Gordy that it could serve as the perfect vehicle for Ross, who at the time was just emerging as a solo artist after her years with The Supremes, to make her film debut.

The saga actually began in 1957 at the Newport Film Festival, where Weston was serving as a publicist, when backstage he ran into Holiday, who suggested he take a look at her autobiography, Lady Sings the Blues, which had just been published. As Weston tells it, the legendary singer told him, “It’s not particularly true, but I think you’ll enjoy it.” Weston, looking to break into film producing, secured an 18-month option on the book for $5,000, which he would keep renewing for the next 13 years until the picture finally went before the cameras. Over the years, he tried to interest a number of actresses in taking on the formidable challenge of playing Holiday onscreen — among them, Diana Sands, Abbey Lincoln and Diahann Carroll.

“Diahann Carroll was seeing Sidney Poitier, and I was involved in a picture with Sidney so he brought her to a screening one night and I asked her,” Weston remembers. “She wasn’t particularly interested in doing Billie Holiday. Abbey Lincoln would have been great in it, but unfortunately her husband Max Roach, the drummer, was forbidding her to do any more movies after she did For Love of Ivy with me.”

Meanwhile, Weston commissioned a script from a young Canadian writer Terence McCloy, which he used to attract director Sidney J. Furie, who’d directed such films as The Ipcress File, starring Michael Caine, The Appaloosa, with Marlon Brando, and Little Fauss and Big Halsy, with Robert Redford. Give his male-oriented résumé, Furie might have seemed an unlikely choice to take on the tale of a brilliant but troubled woman, but Weston says he was impressed by a shot in The Ipcress File of Caine, seen through a pair of his glasses. “The guy who did that shot, he could do my movie,” Weston had decided. For his part, Furie says he wasn’t surprised by the offer, since “when you’re young, nothing surprises you.”

Ross herself came onto the filmmakers’ radar, thanks to a 1969 Look magazine cover story about her emerging solo career, in which she talked about her love of Holiday, saying, “Just listening to Lady Day brings sadness to me, and I’m trying to find out everything about her. I want to sing about blues and sadness, a natural part of life. I’m trying to find out the real psychological reasons Billie Holiday gave up and took to drink and drugs.”

In his biography Diana Ross, J. Randy Taraborrelli argues that Gordy coached Ross to bring up the subject of Holiday in the interview to signal her interest, even though the Motown impresario had already turned down initial overtures from Weston. (Gordy, who is now retired, declined to be interviewed.) But, in any case, both Furie and Weston then set their sights on the glamorous singer. “I had just watched a Motown special where she had done comedy,” recalls Furie. “And I said if she can do comedy, she sure as hell can do drama and she’s a singer and I think she’d be great.”

Joe Schoenfeld, an agent at William Morris, set up a meeting between Gordy, Weston and Furie at Gordy’s Sunset Boulevard office, where they gathered around a pool table. As Furie remembers it, at first Gordy said of Ross, “But she’s not an actress,” to which Furie replied, “Of course, she is. Have you seen your own special?” And so, Gordy was cajoled into agreeing to the project if it could be set up at a major studio. As it happened, Frank Yablans, who’d worked his way up as a sales exec, had just been named president of Paramount Pictures. On his first day on the job, Brad Dexter, an actor friend of Furie’s, walked the Lady script into the new president’s office. By that evening, Yablans had read it and committed the studio to a $2 million production.

Taking liberties with Holiday’s life, the script had combined aspects of Holiday’s three husbands into one character, her final spouse Louis McKay, making their love a central thread of the biopic. “To his credit,” says Furie, “Frank loved the idea of a Black love story. He’d been a salesman, going to exchanges for Paramount around the country, and he understood the public. He said he thought it would work very well.”

Before filming began at the end of 1971, Gordy asked his executive assistant Suzanne de Passe to take a look at the screenplay and tell him what she thought. “I gave him a hundred things,” she remembers, and so Gordy asked her to work with Furie on rewrites, bringing along Chris Clark, another Motown recording artist, as her co-writer. “There were a number of stereotypical things in the script that were sort of offensive, to be honest,” de Passe remembers. “One thing that I recall was a telephone call between Billie and Louis. Billie said, ‘Touch your balls for luck, Louis.’ It was not just stereotypical in some places, but offensive. What Chris and I did was put in things like Billie bringing the red hat to her mother, making it a lot more glamorous and romantic.”

On the romance front, the filmmakers were also looking for a leading man to pair with Ross. One early candidate was Paul Winfield, who would go on to star in Sounder, which would compete with Lady at the ’73 Oscar ceremonies. Recalls Furie, “Berry thought he was a great actor, but he said, “Let’s give those young Black girls what young white girls want. Let’s give them a Black Clark Gable, a good-looking guy.” Weston already had another actor in mind — Billy Dee Williams, who he’d seen a few years earlier in a little off-Broadway play. Says Weston, “I went backstage and I said if I ever make the Billie Holiday movie, I think you would make a great Louis Mckay, and he said, ‘Sure, sure, sure.’  But then two years later, when I was setting the movie up at Paramount, on a Saturday morning, I went to get some ice on Highland, and Billy Dee Williams was standing there. He had no agent and I had no contact, so I couldn’t have found him, but he was standing at the ice machine, and I said, “Come to my house tonight, here’s the address. Berry Gordy and Diana are going to be at a party at my house and you ought to meet them.”

“So he showed up at my house that Saturday night. Diana thought he was very interesting but said he looks too young and then he called me a couple of weeks later and said, ‘I just grew a mustache and I look older,’ so I sent his picture to Diana, and she and I watched a screen test he did for us and she said, “That’s my guy.”

“What was so funny,” remembers de Passe, “is that Billy Dee probably had the worst screen test of all the actors we brought in. He forgot his glasses, he forgot his lines, and yet when his screen test came up, it was so obvious the chemistry he had with Diana. His magnetism was stunning.” Ross herself may have had no acting experience, but she gave herself over to the project completely. “I’ve never seen anyone work so hard and be so dedicated and so committed,” testifies de Passe. “She’s always been someone who did her homework. At one point Berry said, ‘You sound too much like Billie, you need to put more of you into it, because she was walking around with a Walkman and earphones, listening and studying. It was astonishing what she did.”

Furie seconds that, saying, “She’s the greatest improviser I’ve ever known. Some of the main scenes were improvised. We would rehearse a little bit, get an idea where we were going from the script and we would then roll cameras on the improvisation. and after each take, I’d say keep that. She was the consummate pro and not a diva at all.” When she did have moments of doubt, Gordy, who was a constant presence on the set, would reassure her. “When we were filming,” says Weston of Gordy, “He was cooperative and he was fabulous, because he wasn’t afraid of anything or anybody. Diana listened to him and he watched everything and he had a very good eye, and he was very smart and very aggressive, so he was a help during the production of the movie.”

Furie admits that initially there were some tense moments between he and Gordy. “At one point, right before production, there was a bad fight and I walked off,” he says. The studio brought us back together. Barry said, ‘Look, we need each other,’ so I said OK. So there was he and I pushing against each other for the good of the movie. The great thing about Berry, he’s one of the great cheerleaders. Even when there were problems, and there are always problems in getting what you want, it was such a cheerful movie.”

“It was congenial,” de Passe agrees. “Berry actually got to direct a couple of scenes. I think Sidney recognized Berry’s contribution to understanding Diana’s talent and how to bring it out. He recognized it and welcomed it.”  The movie was shot in sequence, which proved fortuitous when Richard Pryor, then a relative unknown, arrived on set for one day of work as Piano Man, Holiday’s accompanist. Says Furie, “He was so incredible, we said, OK, let’s write him into the rest of the movie. We saw the impact of him right away. And he and Diana had great rapport.”

Despite his quick greenlight on the project, Yablans eventually became concerned when the project began to go over budget, and so he summoned Gordy to New York to tell him to quickly wrap up the shoot. As de Passe explains, “it was a unique experience for Paramount. Basically, Berry Gordy ended up buying the film back from them. At the time, Frank Yablans said he’d never put more than two million dollars in a quote unquote Black movie, and Barry, said, “Is there anything I can do?’ and he said, ‘Yeah, write me a check.’” And so Gordy paid Paramount, which remained the film’s domestic distributor, the $2 million it had already invested and agreed to shoulder the remainder of the production’s cost in exchange for some of the foreign rights.

With Gordy in control, Weston says he was shouldered aside, “The last day of production, Berry Gordy sent a man to see me. He said Berry wants to put his name on the production in some form. Here’s $50,000 in cash if you’ll agree to it. I made the mistake of taking the money and agreeing to it. The moment that happened, Berry Gordy became the producer of the movie.” Although Weston’s own name remained on the film, he continues, “I was left out completely from all the publicity releases. The picture was selected to close the Cannes Film Festival, and they wouldn’t even pay for Sidney and I to go there.”

Even before it closed the 1972 Cannes festival — where Ross was introduced to the great performer Josephine Baker on the red carpet — there were signs the movie would be a hit. “It exceeded any dreams I had,” says Furie. “Biographies always get some negative reviews, but all you had to do was see it with an audience and it was like, ‘Wow.’ We previewed the picture in a well-to-do Black suburb of Detroit, very upper-middle-class. Halfway through, we blew out the sound system. So we shut it down. The audience didn’t move for three or four minutes, and then it continued up again and afterwards they were probably the greatest cards in the history of previews.”

The Academy rewarded the film with five nominations — for Ross as best actress as well as screenplay, music, costume and art direction nods. Ross, who had earlier received a Golden Globe award as 1972’s most promising female newcomer, held her breath as Raquel Welch and Gene Hackman read out the names of the best actress nominees, only to see the award go to Liza Minnelli for Cabaret. Several theories circulated at the time. As the daughter of Judy Garland, Minnelli was Hollywood royalty, whereas the Lady team represented the new kids in town. Minnelli herself had failed to turn her best actress nomination for The Sterile Cuckoo into gold three years earlier, so some may have felt she was due. And Cabaret was simply a stronger contender with 10 nominations and eight wins that night. But Weston advances another theory: “Berry Gordy spent so much money on ads for Diana Ross, he antagonized the entire Academy. It was so overwhelming, everyone was commenting on it. And for that reason, she lost best actress to Liza Minnelli. Liza’s performance in Cabaret was good, but nothing compared to what Diana did in our movie.”