Miss Ross enters in a black fur coat. Her hands are slightly nervous—tense against this moment. She is suddenly flanked by a couple of correctional officers, one who tears off her gown for an orange prison uniform, the other jerks her hair back to take her mugshot. In this scene, from the 1972 biopic Lady Sings the Blues, Diana Ross plunges into the painful life of the late, great jazz and blues legend Billie Holiday. “People felt I couldn’t play the tragedies,” Ross told The New York Times at the time, speaking of her bracingly raw performance. “They think I was born with a silver spoon.” Directed by Sidney J. Furie, Lady Sings the Blues is a glowing celebration of Billie Holiday’s legacy as well as a poignant illumination of her stint in federal prison, years of heroin addiction, abusive relationships with men, and lifelong fight for racial equality. Beyond the critical acclaim, the film also made history with the unprecedented number of black creatives they featured, setting the tone for future productions. Now, Holiday’s legacy is being cherished again with a new Lee Daniels’ film, The United States vs. Billie Holiday, starring Andra Day.

Nothing in Ross’s glitzy showgirl background prepared studios, critics, or audiences for her gut-wrenching performance as Holiday. And she brought the icon to life with dazzling style—Ross, a former fashion design and costume illustration major, had a hand in designing “Lady Day’s” most iconic outfits for the film, collaborating with Norma Koch and Bob Mackie. The singer and the production crew were showered with awards, earning five Oscar nominations, with Ross receiving a nod for Best Actress.

Prior to her silver screen debut, Ross led the Supremes to the top of the charts 10 times in less than three years. This Motown triad—Ross, Ms. Wilson, and Florence Ballard—became vehicles of social change, breaking the race ceiling by weaponizing fashion and defining the way many women wanted to look. From their dreamy sequined gowns to meticulous spider lashes, these powerhouse women of color created a personal style that was singular, recognizable, and instantly trendsetting.

With a sultry soprano voice, Ross brings an indelible savoir vivre to Lady Sings the Blues. Filled with more than a dozen of Holiday’s songs, Ross, grounded in her soulful roots, never tries to imitate the “Strange Fruit” singer. Rather, there was an uncanny echo, a suggestion, where her style pays homage to Holiday’s raspy, multitudinous intonation. Now, at 76 years old, Ross shows no signs of slowing down and in true hero form, received the Presidential Medal of Freedom from Barack Obama.

She is still the only artist to have No. 1 singles as a solo artist, as half of a duet, as a member of a trio, and as an ensemble member. And with Ross’s seemingly eternal brilliance, we find, to paraphrase Holiday’s own hits, no greater thrill than what she continues to bring to us.