Billie Holiday’s tragic life bears similar “Fruit” for two historic Oscar moments nearly a half century apart.

(April 24, 2021).  When the nominations for this Sunday’s 93rd Academy Awards were announced back in March, many folks recognized the historic simultaneous inclusion of two Black women in the category of Best Actress in a Leading Role, both for playing legendary music figures of the early-to-mid 20th century.  

Viola Davis received a nod for her portrayal of blues singer Gertrude “Ma Rainey” Pridgett.  It’s Davis’ history-making fourth nomination in either a lead or supporting actress role.  She received two nods for her supporting roles in the movies “Doubt” and “Fences” and two more for her lead roles in “The Help” and now “Ma Rainey’s Black Bottom,” a fictionalized account of a recording session of the titular song during the 1920s.

Davis is already the most nominated Black woman in Academy Awards history with her four nods.  If she wins Sunday, she’ll be the first African-American to take home two trophies.  She won in 2017 for “Fences” – which, along with “Black Bottom,” was another adaptation of an August Wilson play that was part of his famous ten-play “Pittsburgh Cycle.”

But it’s Davis’ counterpart in this year’s Best Actress field that draws even sharper parallels to history with her nomination.

Andra Day in 2021’s “The United States vs. Billie Holiday”

That would be singer/actress Andra Day, who is nominated for her raw portrayal of the tragic and iconic jazz/blues singer Billie Holiday in the 2021 film “United States vs. Billie Holiday.”  It’s Day’s first nomination – a remarkable one at that – as it is also her first acting role in a major feature film.  

With both Davis and Day getting noms this year, it’s the first time in nearly half a century that two Black women have been nominated at the same time in the Best Actress category.  You’d have to go back to 1973 to find the first and only other time that happened.  

That was when both Diana Ross and the late Cicely Tyson were nominated for their roles in the 1972 films “Lady Sings the Blues” and “Sounder,” respectively.  Both lost to Liza Minnelli for her stint in “Cabaret.”

The parallels between now and then are uncanny when considering that Ross and Day received nominations for their portrayals of the same woman, Miss Holiday, a figure whose story was so tragic that it seems to write itself for Hollywood screenplays and dramatic depictions.

And like Day in 2021, Diana Ross was nominated for her first acting gig in a motion picture, one helmed by her Motown label boss at the time, Berry Gordy.

The fact that both Day and Ross received Oscar nods for their first major acting gigs is even more compelling when considering that neither singer/actress has won in a competitive category for the equivalent awards in their main entertainment field: singing.  That would be the Grammys. 

Diana Ross famously received 12 Grammy nominations and zero wins, while Andra Day has received three Grammy nods (including one for her signature tune “Rise Up”) and no wins.  It’s interesting that Billie Holiday also never won a Grammy, although she received two posthumous nominations in 1961 and 1973.  Ms. Holiday and Ms. Ross have both since received Lifetime Achievement awards from the Grammys.

But it’s Andra Day who now has the chance to do what Diana Ross didn’t back in 1973, and that is bring home the Oscar for playing one of the most tragic figures in American music history.  Day – who took home this year’s Golden Globe for her portrayal – has at least a decent shot at actually winning the Oscar.

That possibility is where the parallels between 1972/73 and 2021 begin to fade, both for the actresses involved and for the two films depicting Ms. Holiday.

“Lady Sings the Blues” was a lifetime portrayal, as the movie covered Ms. Holiday’s childhood (which was marred by a rape) through her rise to fame (which began with her singing in seedy Harlem nightclubs) and her marriage to third husband Louis McKay (played by Billy Dee Williams).

Diana Ross in “Lady Sings The Blues” (1972)

Ross played Holiday as a sympathetic figure, one whose life was destroyed by heroin and alcohol but one the audience could like, or even love.  The role was clearly a stretch for Ross whose good-girl image before then made her portrayal of the drug-addicted mess that Ms. Holiday was all the more compelling.

Who could forget the opening scene where Ross’ Holiday was strapped in a straight jacket while in solitary confinement at a sanitarium after being arrested for illicit drug use?  Or her violent confrontation with Williams’ character in a desperate attempt to get access to her stash for another bathroom binge?  

And what about the drug-induced stupor that prevented her from being of any aid to her “Piano Man” (amazingly portrayed by the late Richard Pryor) after he was beaten to a pulp by two thugs to whom he owed drug money?  

Those scenes alone likely secured the Oscar nom for Ross, who appeared on the big screen unlike anything anyone had seen of her before.  She was at times strong and demanding – as someone of Billie Holiday’s talent and stature must have been – but also vulnerable and defenseless, playing all traits convincingly.  It was no wonder that Ross’ portrayal was recognized by the Academy, even at a time when Black women – and Black people in general – had achieved so few nominations in the awards’ history.

Diana Ross sings “Good Morning Heartache” in “Lady Sings The Blues” (1972). It was a top-40 hit for Ross the following year.

Yet while Ross played Holiday as somewhat sympathetic and completely fractured, Day took her in a different direction entirely for “U.S. vs. Billie Holiday.”

Day’s Billie was raw and undaunted.  She was rarely seen without a lit cigarette and could utter the words “nigga” and “bitch” with the best of them (Diana Ross’s character used them on occasion, but perhaps not as authentically and definitely not as much).  

Day’s Billie also wasn’t afraid to fight her abusers – chief among them husband McKay (portrayed as a much more sinister character in this film by actor Rob Morgan than the more likable guy Billy Dee Williams gave us).

Andra Day’s portrayal of Billie Holiday wasn’t so much of a stretch for the singer as it was for Ross, who – at 28 years old at the time – had to convince audiences that she was a sweet, naive 14-year-old girl at the beginning of “Lady Sings the Blues.”   

The 2021 film largely focused on Billie’s life as an adult, and even more specifically on the Feds’ pursuit of her in their attempts to racialize the war on drugs – and to stop her from singing her controversial best-seller, “Strange Fruit.”

“Strange Fruit” was thus the centerpiece for Day’s movie, a song that itself was inspired by Billie Holiday witnessing the aftermath of a Black man’s lynching on a country hillside in the Deep South.  That scene was eerily depicted in both films, but it clearly was the focus of Day’s character, and it likely inspired her decisions not to divulge her drug sources even as she lay dying in a hospital in 1959 with the feds still in hot pursuit.

Andra Day performs her version of “Strange Fruit,” a modern-day take on the anti-lynching protest song.

The fact that we even see Billie in her final moments during the more recent film is another key difference.  In “Lady Sings The Blues,” Ross’ character is shown singing at Carnegie Hall near the end as the film’s producers choose instead to chronicle her final demise by flashing related newspaper headlines on screen.  It’s almost as if the filmmakers didn’t want Diana Ross seen in that final lifeless state. 

Gone also from “Lady Sings The Blues” were any real love scenes.   After all, it was 1972 and we are talking Queen of Glamour, Diana Ross.  In “The United States vs. Billie Holiday,” however, Day engages in a pretty hot, x-rated romp with Black federal agent-turned-fan-turned-lover Jimmy Fletcher (actor Trevante Rhodes).  Viewers likely could never have imagined Ms. Ross “getting into position” the way Ms. Day did on that hotel bed, especially in 1972.

But perhaps the biggest reason that Day’s portrayal wasn’t as big a stretch for her as it was for Ross is the association of either actress – or the lack thereof – to Holiday.

Andra Day’s stage surname was indeed inspired by “Lady Day,” Billie’s nickname.  Her singing style is more closely aligned to Billie’s than Diana Ross’ is.  And without the superstar name and voice recognition that Diana had already achieved by 1972, it’s a lot easier for fans to picture Day as Billie in 2021.

While all of this makes Diana’s portrayal of Billie Holiday all the more remarkable in 1972, it certainly doesn’t detract from what Andra Day was able to do with the character in this year’s film.

In this one, we got to see a defeated but defiant Billie Holiday – warts and all – as she navigated the challenges of stardom, a conniving husband, and a racist government set on accelerating her demise.

Andra Day’s Billie Holiday may not have been as likable as Ross’s as a result, but then who would be?

Here’s hoping that this “Lady Day” – Andra Day – gets the Academy Award that eluded Diana Ross and so many other Black actresses before and since her own captivating portrayal of the one and only Ms. Billie Holiday nearly a half century ago.

Billie Holiday (1915 – 1959)

DJRob

P.s.: Richard Pryor should have received an Academy Award for his extraordinary performance as “Piano Man” in “Lady Sings The Blues.”

P.s.s. Billie Holiday should have been in the Rock and Roll Hall of Fame decades ago.

P.s.s.s. How is it that neither Billie Holiday, Diana Ross nor Andra Day have ever won a Grammy award?

DJRob is a freelance music blogger from somewhere on the East Coast who covers R&B, hip-hop, pop and rock genres – plus lots of music news and current stuff!  You can follow him on Twitter at @djrobblog.

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