Andra Day edged out for Oscar honors, but her film portrayal of iconic Billie Holiday a triumph regardless

Andra Day didn’t win the best actress Oscar Sunday at the 93rd annual Academy Awards for her riveting title-role performance in “The United States Vs. Billie Holiday,” a category that was won by Frances McDormand for “Nomadland.”

But Day’s nomination for her portrayal of Holiday — the legendary jazz singer and civil rights champion — was a victory in itself for the 2003 San Diego School of Creative and Performing Arts graduate.

Her shape-shifting performance as Holiday marked her debut film performance of any kind. Moreover, she is only the fifth best actress contender in Oscar history who was nominated for their debut film performance

“If they put icing on the cake with a cherry with some kind of award, that’s great,” said Bill Doyle, Day’s now-retired San Diego School of Creative and Performing Arts theater teacher. He pivotally introduced her to Holiday’s music when Day, now 36, was 11 or 12.

“But the work she has done won’t change and the work is what I’m unbelievably proud of,” Doyle continued. “Andra’s place in the industry has changed, by virtue of the work she did (in the film). And now she has a voice, not just as an actress on screen but as a powerful African-American woman with a political voice that is important in this time. Of course, I would have been goofy with happiness if she won (the Oscar). But it doesn’t diminish anything for me (that she didn’t).”

Coming on the heels of Day’s Feb. 28 Golden Globe win for Best Motion Picture-Drama Actress, her Oscar nomination was historic even though she didn’t win. Day and Viola Davis were the first pair of Black nominees in the Academy Awards’ leading actress category since 1973, when Cicely Tyson was nominated for “Sounder” and Diana Ross was nominated for “Lady Sings the Blues” (in the same role as Holiday that Day would play nearly 50 years later).

Only four other actresses in Oscar history — Marlee Matlin (1986), Barbra Streisand (1968), Julie Andrews (1964) and Shirley Booth (1952) — won the best actress trophy for their first film role. None of them had to undertake as many challenges to play their parts as Day in her shape-shifting portrayal of Holiday, the immensely gifted and embattled jazz and blues singer, who died in 1959 at the age of 44.

Holiday’s stardom and devotion to civil rights made her a constant target of persecution by the FBI and the U.S. government’s Federal Bureau of Narcotics in the 1940s and ‘50s.

After being cast by director Lee Daniels to portray the legendary singer, Day lost 39 pounds in her quest to simulate Holiday’s heroin-ravaged appearance. Day also took up drinking, smoking and cursing to better capture the essence of Holiday, whose signature song, “Strange Fruit,” is a chilling evocation of the brutal systemic racism Black Americans were subjected to before and after World War II.

“I was trying ... to show what Billie might have looked like when she was skinny and on drugs,” Day noted in a February Union-Tribune interview. “It’s not particularly a pretty sight.”

Andra Day arrives at the Oscars on Sunday, April 25, 2021, at Union Station in Los Angeles.

(Chris Pizzello / Pool Photo)

Day herself was a striking sight during the telecast, for which she wore a gold Vera Wang gown. She also earned earned a chorus of laughs during a segment in which nominees were asked to guess if certain songs had won or not won an Oscar, or if the songs had not even been nominated.

Using some choice profanities, which were bleeped out from the telecast, she opined that Prince’s classic “Purple Rain” was simply too great and too Black to have won an Oscar. (In fact, in 1985 Prince — who died five years ago this month — won the now-defunct Best Original Song Score category with “Purple Rain.”)

‘Lady Day’ begets Andra Day

Born Cassandra Monique Batie in Edmonds, Wash., she moved to San Diego at the age of 3 with her family. Years before being cast in her first film, she adopted the stage name Andra Day in honor of Holiday, who was fondly known to fans as “Lady Day.”

“We have been celebrating Andra’s accomplishments for several years, starting with when she was first nominated for a Grammy Award, and we celebrated her when she performed at one of our annual benefits,” said San Diego School of Creative and Performing Arts Principal Timothy E. Farson.

“Anytime our students can see someone that looks like them and who loves what they do in the arts is incredibly powerful and inspirational.”

Day’s remarkably realistic portrayal of Holiday earned praise from another of her former teachers here.

“It was a tough role, and very draining emotionally,” said Gail McKinney, the San Diego School of Creative and Performing Arts’ now-retired vocal director. “Because the character of Billie Holiday is so much the opposite of who and what Andra is, she had to make a lot of adjustments to her psyche to become Billie, and I was just awed by how she did that.”

Day is not the first San Diego-bred actress to have vied for a best actress Oscar. Annette Bening and Michelle Williams have each been nominated four times, both for starring and supporting roles. Day’s Oscar nomination is still a victory not just for her, but for the community where she got her start and — in particular — for the San Diego School of Creative and Performing Arts. Its other notable alums include actress Sara Ramirez and “Jersey Boys” Broadway musical star Christian Hoff.

Day’s rise to acclaim is also a source of pride for her former classmate Jessica Mays, who was in Los Angeles Sunday to help Day get ready for the Oscars ceremony.

“Her success means everything to me, just because I’ve seen her build from the bottom up,” Mays said. “It’s crazy to me people are just learning about her now because she’s been a star her whole life. So it’s very fulfilling to watch my friend — and I call her my sister — succeed, because she’s worked hard for it. ...

“And it’s extremely important that Cassandra can advocate for the arts and for young people, and she has such positivity. The fact she is Black, a woman of color, is important to my three daughters and to anyone of color to see that what Andra accomplished is not out of their grasp.”

Day’s grasp on her film career appears set to expand. She and “The United States vs. Billie Holiday” director Daniels are now developing ideas that could see Day stretch her creative wings and co-direct, co-produce or co-write.

But music remains the first love for Day, who was championed early on by Stevie Wonder and who scored her breakthrough hit record in 2016 with her inspirational song of empowerment, “Rise Up.”

Her second album is due out June 2 on Warner Bros. Records. It will include “Tigress and Tweed,” a song she co-wrote for “The United States vs. Billie Holiday” soundtrack. The lyrics to “Tweed” encapsulate Day’s journey to prominence: Fruit stand tall, these roots go deep / Strange fruit bussin’ on these thieves / Ancestors don’t take defeat / Left the scent of victory …