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A powerful R&B singer and songwriter, Andra Day was challenged like never before when she was cast to play the lead in The United States vs. Billie Holiday, a role which won her a Golden Globe award for best performance by an actress in a motion picture. Here, she opens up about her new career path, her new album, and why she actually named herself after Lady Day

For Andra Day, portraying her idol, Billie Holiday, came with many challenges, chief among them finding the legendary jazz singer’s voice. “First, was the tone,” explains the singer-now-actor who made her debut in the film The United States vs. Billie Holiday on February 26. “Emulating her is something that I’ve done before, just because I love her. Sometimes I sing her songs in the tone of her voice. But to actually not just emulate her, but to become her, so that the emotion was filling and informing the tone—that was a different thing.” 

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The songwriter, who became a radio and awards show mainstay with her 2015 massive hit single “Rise Up,” had no acting experience beyond participating in musical theater in performing arts school and appearing as a singer in 2017’s Marshall. “It really was a crash course, a lot of hard work, and the most challenging thing I’ve ever had to do in my life,” says the 36-year-old Day. Her excitement and nervousness around the project are palpable, even over the phone, and she comes across much more down to earth and accessible than her regal stage presence suggests. “But it was also one of the greatest, most rewarding things I have ever done.”

At a time when being either an influential Black artist or a Black activist was enough to put you in the U.S. government’s crosshairs, Billie Holiday was both. Her addictions to cocaine and heroin made her an easy mark for the Federal Bureau of Narcotics (FBN), but it was her 1939 anti-lynching protest song “Strange Fruit,” which helped galvanize the civil rights movement, that made her a prime target. The United States vs. Billie Holiday, available on Hulu, explores the relationship between Holiday and Jimmy Fletcher (Moonlight’s Trevante Rhodes), a federal agent assigned to stalk the singer. 

When she first came to fame, Day rocked a signature style—headscarf, curly bangs, hoop earrings, and sharply winged eyeliner—resembling an extremely glamorous Rosie the Riveter. Taken together with her deeply soulful voice, reminiscent of Aretha Franklin and Amy Winehouse, she appeared to belong to an entirely different era, so casting her in the role of Billie Holiday would seem to have been a no-brainer. Nabbing the part, however, was no easy feat. Day worked with acting coach Tasha Smith to prepare for three separate auditions—one on tape and two in person. But she was determined; drawn to the role especially because of the story it tells. “Once I found out the movie would be about the false war on drugs, [which is] really just the war on race, I was like, ‘OK, this is an opportunity to vindicate her legacy,’” Day says of Holiday, who suffered from cirrhosis and died while under arrest for drug possession in a New York City hospital bed at only 44 years old. “As a fan of hers, I wanted to do that.”

Finding Holiday’s voice, says Day, meant being “very, very unkind” to her own. “Singers usually stay warm, wrap our throats up with a scarf and drink warm tea with honey and lemon,” explains Day. “This was all cold weather, no jacket, smoking cigarettes, drinking alcohol, yelling—the complete opposite of what you should do as a singer. But it was very important to me because you need her voice,” she says. “I look at her voice as a scroll, upon which all of the trauma is written—every hit, every minute in prison, every cigarette, every sip, every slam of heroin or cocaine, but also all of her triumphs—it’s all written on the scroll of her vocal cords.”

“I look at her voice as a scroll, upon which all of the trauma is written—every hit, every minute in prison, every cigarette, every sip, every slam of heroin or cocaine, but also all of her triumphs—it’s all written on the scroll of her vocal cords.” 

If Holiday’s life experiences were imprinted on her voice, then certainly Holiday’s voice itself is part of the experience that in turn shaped Day. “I actually think I’m in love with Billie Holiday. She is my biggest inspiration, musically,” says Day, who was introduced to Holiday when she was just 11, in her hometown of San Diego, California. “I heard her song ‘Sugar’ and then I heard ‘Strange Fruit.’ Even though I was too young to fully understand, I could hear her willingness to sacrifice, and I could hear a weight in her voice. It meant everything to me.” Day went on to read Holiday’s memoir, Lady Sings the Blues, which deepened her fascination with the complex singer. She would sometimes style her hair in a bun and adorn it with a large gardenia—Holiday’s trademark look. Day’s stage moniker was even inspired by Holiday. “My actual legal name is Cassandra Batie,” she says. “I just chopped my name in half to Andra, and then I added the Day because of her—Lady Day.” 

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While the widespread success of “Rise Up”—which Day performed at the White House, the Grammys, and across daytime and late-night TV in the months following the song’s release—may have made her appear to be an overnight star, Day had been working toward her big break for 15 years before it came. A year after designer Kai Millard Morris saw a video of Day singing at a strip mall and shared it with her then-husband, Stevie Wonder, he connected Day with Adrian Gurvitz, who would produce her first album. “Things started moving for me in music way later than I thought they would,” says Day, who was 31 when she first got connected with Gurvitz. While she waited, Day worked various jobs in both Southern California and New York, including account manager, house cleaner—she even had a gig with an events company. “We’d show up to little kids’ birthday parties in these suits as characters like Minnie Mouse, Dora the Explorer, and Elmo,” she says. “It was a long, long process. I was just inching upward for such a long time.” 

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Since 2012, Day has lived in the Los Angeles area, where her mother and two cousins—one of whom is a teenager—now live with her. Last May, she released “Make Your Troubles Go Away,” a comforting ballad originally slated for her album Cheers to the Fall that was later bumped in favor of “Rise Up,” and Day donated proceeds to people affected by the COVID-19 pandemic. She also spent the months of forced rest recovering from the grueling experience of making the film. 

“I’m not exaggerating—there were no easy days.” says Day. “It was a little eerie during filming to look out at an audience and see Black people way up in the balcony, and white folks sitting in the front. It was weird to see that segregation. There was this feeling of, ‘We’re still dealing with some of these things right now.’ Some things have become more complex and nebulous, but they haven’t been done away with. That was a really painful part [of making this movie]. But as an actor on set, you have to use that pain. It was difficult, but it was cathartic at the same time.” 

Some of that emotion can be heard on Day’s much-anticipated second album, which she expects to release this spring. “I actually couldn’t help it. A lot of Billie’s DNA made it onto this record,” says Day. “There’s triumph, there’s defiance, there’s melancholy. I’m so excited about the song that Raphael Saadiq and I wrote for the end title. It’s called ‘Tigress and Tweed,’ and it’s my favorite thing that I’ve ever written. It will also be the opening track to my record.”

As filming wrapped on The United States vs Billie Holiday, Day’s costars assured her, “You’ll never work this hard again in another role.” Though she responded at the time, “You’re right, because I’m never taking another role,” today Day admits she’s “inspired to develop stories that center and celebrate Black women. “Someone told me that one reason I’ll never have to work this hard in a role again is because there just aren’t a lot of meaty roles for Black women,” she says. “I was floored by that comment. The way we succeed, the way we overcome, the way we support, the way we lead—everything. Who could have meatier stories than Black women?”   

By Sabrina Ford
Photographer: Myriam Santos
Hair Stylist: Tony Medina 
Makeup Artist: Porsche Cooper
Stylist: Wouri Vice
Clothing: Prada

This article originally appeared in the Spring 2021 print edition of BUST Magazine. Subscribe now!

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