Though Diana Ross had previously appeared in two films while a member of the Supremes, it wasn’t until the early 1970s when Berry Gordy began to focus on making Ross an actress. In late 1971, Motown announced that Diana Ross was going to portray jazz icon Billie Holiday in a Motown-produced film loosely based on Holiday’s autobiography Lady Sings the Blues (1956) written by Holiday and William Dufty. The movie co-starred Billy Dee Williams as Holiday’s lover, Louis McKay. The cast also included comedian Richard Pryor as the “Piano Man”.
Some critics ridiculed Ross’s casting in the role. Ross and Holiday were considered to be “miles apart” in vocal styling and appearance. Undeterred, Ross immersed herself in Holiday’s music and life story. She went to drug clinics and talked with doctors as research for the role. Ross made a crucial decision when it came to interpreting Holiday’s music. Instead of imitating Billie Holiday’s voice, Ross focused on Holiday’s seemingly inimitable vocal phrasing.
Opening in October 1972, Lady Sings the Blues was a major success, and Ross’s performance was lauded and well received. Jazz critic Leonard Feather, a friend of Billie Holiday, praised Ross for “expertly capturing the essence of Lady Day.” In 1973, Ross was nominated for both a Golden Globe Award and an Academy Award for “Best Actress”. Ross along with fellow nominee that year Cicely Tyson, were the second African American actresses to be nominated for an Academy Award for Best Actress after Dorothy Dandridge. Ross won the Golden Globe for Best Newcomer, but lost the Best Actress Oscar to her friend Liza Minnelli for her role in Cabaret. The soundtrack album for Lady Sings the Blues reached number one on the Billboard 200 for two weeks and broke then industry records by shipping 300,000 copies during its first eight days of release. The double-pocket custom label record is one of Ross’s best-selling albums of all time, with total sales to date of nearly two million copies.
My only company was a cat I liked who sometimes used to help me in and out of my gowns before I went on stage. When he wasn’t doing that, he was helping himself in and out of them. We took to calling him Miss Freddy and he was always good for a laugh. He was close enough to my size, too, so a fitter or dressmaker could work on him and not bug me. He was crazy for a lynx cape I had. It looked better on him than it did on me, too. Although the police didn’t always think so. They’re so narrow-minded they were always picking on him for being overdressed. I’d have to go down to the station and bail him out–and whatever part of my wardrobe he had on him.