It's Andra Day Season

In her film debut, the "Rise Up" singer shows another side of her idol, Billie Holiday.

by Angelica Jade Bastién
Andra Day posing in a sheer green maxi dress

Thirty minutes into her debut live-action film, The United States vs. Billie Holiday, singer Andra Day bares all. The scene is nestled after Billie Holiday, played by Day, is ripped from the stage by law enforcement for attempting to sing her monumental work, the then-controversial “Strange Fruit.” To deal with the pain, as Holiday often did during the second half of her life, she reaches for heroin, turning to her friend, drug provider, and fellow addict Joe Guy for respite.

Here, as elsewhere in the film, Day plays it full tilt: Her curled hair unfurling, a thin film of sweat resting on her brow. She stumbles around the apartment wearing only a longline bra and girdle of peachy silk. She slips on Joe’s coat and heads out for ice cream, her silver heels clicking against the hardwood floors, but when she opens the door, she’s faced with the might of the federal government in the form of a narcotics task force, headed by an agent who had been posing as a starstruck soldier, Jimmy Fletcher (played by Moonlight’s Trevante Rhodes). “You wanna search me?” she spits before undressing completely, viciously throwing her clothes to the floor. She stretches out her arms, and the camera takes her in from the waist upward. It’s a moment primed not on sex appeal but on baring her internal contradictions and refusal to be easily controlled, which is what this role required of Day to pull it off.

Day will be the first to tell you that this role wasn’t an obvious fit for her. “Let's just say sis is not a sex symbol,” she says, discussing the scene over Zoom from her Los Angeles home. It’s not that Day is an unknown figure. The 36-year-old singer’s 2015 debut album, Cheers to the Fall, introduced her to the world as evocative of Adele and Amy Winehouse, with an old-school flair and a Lucille Ball-styled headwrap. The album was nominated for two Grammys, and its hit single, “Rise Up,” has only grown more popular over the past five years, emerging as a hopeful anthem for the fractured American culture that Black Lives Matter seeks to refashion. She performed the song at the 2016 Democratic National Convention, in front of the mothers of Trayvon Martin and Sandra Bland, and again last week for the inauguration ceremonies of the 46th president of the United States, Joe Biden. Reflecting on the nature of her growing fame, Day, who describes herself as spiritual but not religious, says, “I just want to be representing God in every sphere that I go to, and I want people to encounter that love, and that's the thing for me.”

All this to say that The United States vs. Billie Holiday, which comes out Feb. 26 on Hulu, will act as a reintroduction for fans who only know Day for her uplifting, soulful R&B numbers. For those whose radars she’s managed to fly under, it’s a bold introduction.

Chanel top, skirt, and bra; Mateo earrings, Chelsea Paris shoes.

Based on the true story of how Holiday became a pawn in the FBI’s fledgling war on drugs beginning in the mid-1940s, The United States vs. Billie Holiday is proudly in line with the previous work of its director, Lee Daniels, like the sweaty and deranged southern fable The Paperboy and the arch poverty exploration Precious. Touched by camp and powered by a lavish outlook on life, Daniels’ films require an intensity that Day more than matches with bawdy fierceness wrapped in gorgeous Prada gowns.

Speaking to her directly after watching The United States vs. Billie Holiday is a bit of a trippy experience, given how different the star is from the woman she transformed into. Day looks exceedingly comfortable yet chic in a black sweater, her honey brown hair slicked back into a high bun of soft curls and her gold hoops catching the late afternoon light. Her manner is breezy yet grounded, which is perhaps due to her devotion to faith, family, and Southern California. Though born outside of Seattle, Washington, she says, “I consider San Diego my city.”

Born Cassandra Batie, Day is one of four children, raised by a father who was in the Navy and a mother who worked as a facilities manager. She attended a San Diego performing arts middle and high school, but her education began singing along with her dad’s records. “My earliest memories are probably of Whitney Houston, because of her voice. The bigness of her voice,” she says. “And that was the thing to aspire to when we were really, really young … that you could hit those long belts and those big notes.” Her parents went through a messy divorce when she was 18 — “It involved some people in our community that we would hope that we would have trusted. … I think our family was really shook by that and how it happened more so than what happened” — but now they’re all on good terms, and are collectively a bedrock for Day’s understanding of herself and her place in the world.

Fendi dress, Calle Del Mar bra and brief, Mateo earrings and ring, Temple St. Clair ring, Khiry ring, Wing & Weft gloves, Pamela Mann socks, Manolo Blahnik shoes.

Day was living with her mom in an apartment in San Diego, working odd jobs like as a kids’ party entertainer and posting jazzy covers of pop songs to YouTube when her break finally came in 2010. She had driven up to Malibu to perform at a strip mall, where she was discovered by Stevie Wonder’s then-wife Kai Millard Morris. Two Grammy nominations, two White House visits, and an Apple commercial co-starring Stevie Wonder later, Day’s mom now lives with her. She hangs out with her siblings and cousins all the time, commits to daily morning devotionals, and calls both parents her best friends. She recently had to spend her 36th birthday in New York, filming her New Year’s Eve ball drop-headlining performance, and, she says, “When I got back home, my mom had decorated the house and done something really cute.”

One of the first things you come across when trying to learn more about Day’s life is that, unlike pretty much every artist on the come-up, she isn’t active on social media. Her Instagram has only a handful of posts, I point out. “Don't say that!” she says, her hands raised and her acrylics, cream with black tips, fluttering. Speaking more to her assistant on the line than to me, she adds, “If anybody's listening, I'm great, and I'm getting so much better at it. No, I'm kidding! I'm kidding! I honestly am terrible at it.”

Day sometimes feels the pull to be more online — for example, she wishes she had posted a picture for the founders’ day of her sorority, Delta Sigma Theta, which she became an honorary member of in 2019. “I was so ashamed of myself. I was like, ‘Girl, really? You missed Founders’ Day?’” She says her social media reticence is a byproduct of not knowing how to play that specific game, but it’s evident she feels the risk of putting too much of yourself online. “I think [social media] is like a flame. It's very easy once you get caught up in it to be consumed by it. I felt it in myself sometimes.”

Miu Miu top and skirt, Mateo earrings and ring, Temple St. Clair ring, Khiry ring, L'Enchanteur ring.

Day didn’t think she was right for the role of Billie Holiday, and director Lee Daniels agreed with her assessment. “To be honest, I did not want to do it at all. I was, ‘Absolutely not, top to bottom. Nope, nope, nope, nope,’” she says. Day loves Holiday — her stage name is an homage to Holiday’s nickname, Lady Day and she’s been a fan of the icon since she was 11 years old — and she didn’t think she was good enough. “Why would I play her and destroy her legacy? I’m not an actress.” She didn’t want to remake the 1972 Holiday biopic, Lady Sings the Blues, starring Diana Ross. “Diana's performance was just so seminal, and it was perfect. Though it was not the full, accurate story of her life, they did what they could do.” Meanwhile, she says, “On the other side of it, Lee was also, ‘Nope, don't want to work with her. She's a singer, she's not an actress.’”

“The world will be able to see Billie Holiday and say thank you to her, and thank God for her for being the godmother of civil rights. Because she was.”

But when their respective managers convinced them to meet at the Soho House, they connected to a surprising degree. “We talked about our mutual insecurity,” Day says. “I saw in him a desire to tell Billie Holiday's story authentically.” Day read the script, by playwright Suzan-Lori Parks and based on Johann Hari’s book Chasing the Scream: The First and Last Days of the War on Drugs, which explores the evolution of government intervention with drug use profiling people including Holiday and the first commissioner of the Federal Bureau of Narcotics, Harry J. Anslinger, who is played by Garrett Hedlund in the film. “That was revelatory for me, because I said, ‘Oh, we're not redoing Lady Sings the Blues — we're actually going to vindicate her legacy. And the world will be able to see her and say thank you to her, and thank God for her for being the godmother of civil rights.’ Because she was.”

Aliétte dress, Calle Del Mar bra and brief, We Love Colors tights, Mateo earrings and ring, Temple St. Clair ring, Khiry ring, Manolo Blahnik shoes.

The prospect of honoring that aspect of Holiday’s life fueled Day in the lengths she went to authentically interpret her. She cut off her hair, which she had grown all the way down her back, and she dropped from 163 pounds to 124. “I wanted a period body. I wanted my breasts to sag, I wanted my skin on my stomach to sag, I wanted things to look uncomfortably skinny or loose,” she says. “I just thought it would be complete vanity if I said, ‘I'm about to be naked, let me make sure I look the best I've ever looked.’ Like, nah, bro, that's not how she would have looked. I would not have been able to be in character and be in her headspace if I'm just — abs, booty tight, booty high — you know what I mean?”

She worked with an acting coach, Tasha Smith, and a dialect coach, Tom Jones, to find the raspy, bourbon-soaked tenor of Holiday. “I don't smoke cigarettes, but I guess now I have a year and a half, maybe two years of smoking cigarettes under my belt.” Although Day doesn’t drink, she traded her hot teas for ice water and gin. “What you hear in Billie Holiday's voice is her history, and her legacy, and every experience she's had. And I think in order to get that, I had to.”

“Why are we not allowed to explore all of the dynamics of our humanity the way — for I will just not parse words here — the way we see in white characters?”

She also met with former heroin and cocaine users. Two men, in particular — she recalls one of them as the 25-years-sober owner of a rehab center, the other a young man barely a year in his sobriety — taught her how to tie off, how to hold the syringe (which would have been glass, heavier than modern plastic), and the type of track marks a large gauge needle would have left. The lingering signs of the younger man’s dependence left her “concerned to the point of tears.”

“As he watched me practice what he had just taught me,” she says, “I looked in his eyes and I could see, I mean, nothing else was in the room for him. Everything else fell away and I could see him sort of zero in, focus like a scientist. … He helped me to truly understand everything I needed about the moment before, and what it is like to need this drug.”

Brandon Maxwell top, skirt, and belt; Calle Del Mar brief, Sterling King earrings.

Day anticipates that the film may face criticism for addressing Holiday’s addiction, as well as her bisexuality. She also thinks Holiday’s legacy is powerful enough to withstand such scrutiny. “I love seeing the mess of Billie Holiday, because we're human. Why are we not allowed to explore all of the dynamics of our humanity the way — for I will just not parse words here — the way we see in white characters?” she says. “She was actually bisexual, and why does that offend you? And why can't we have that conversation? ‘Well, I hope they don't paint her as a drug addict.’ She was an addict… The government wanted her to be an addict and to hang herself. But she was. She struggled.”

The United States vs. Billie Holiday comes out during a fascinating time for Black Hollywood. Whether progress has truly come to the entertainment industry is yet to be determined, but at the very least, audiences are witnessing a surge of representation behind and in front of the camera. Day sees Daniels’ take on Holiday as an example of the corrective power of Black creators. “Most people don't understand that, particularly Black stories but lots of stories of marginalized people, our narrative has been intentionally suppressed and intentionally manipulated,” she says.

Sportmax top and skirt, Temple St. Clair ring, Mateo ring, Khiry ring, L'Enchanteur ring, Brother Vellies shoes.
Chanel top, skirt, and bra; Mateo earrings.

Day aims to walks in the same lineage as Holiday, blending political activism with the artistic in an effort not just to limn the change that needs to be made in this country but to demonstrate how Black people are, in fact, whole. That, certainly, was the aim of her inauguration performance last Wednesday, in which she gave a soaring performance of “Rise Up” overlooking the Black Lives Matter mural in Hollywood, intercut with footage of 9-year-old skater Kaitlyn Saunders performing in Washington, D.C.

She says people have asked her how she can support President Joe Biden, considering his role in the 1994 Crime Bill that spurred mass incarceration of Black men. “[Biden] acknowledged it and said, ‘It was wrong, I am sorry,’” she says. “And to me, I was like, that’s huge. I’m just happy to have a president in office that can apologize again, or acknowledge when something was a mistake. And needless to say, the joy of having Kamala Harris in this seat as vice president...”

She thinks it’s a time for healing and for being heard and, on a personal level, for gratitude.

“I'm just, I'm happy to be a part of this, not just this moment in history but to be able to celebrate it.”

Miu Miu top and skirt, Mateo earrings and ring, Temple St. Clair ring, Khiry ring, Le Enchanteur ring, Pamela Man socks, Amina Muaddi shoes.

Top Image Credit: Aliétte dress, Calle Del Mar bra and brief, We Love Colors tights, Mateo earrings and ring, Temple St. Clair ring, Khiry ring.

To shop Andra Day's looks from the cover shoot, click here.

Photographer: Erik Carter

Stylist: Tiffany Reid

Hair: Tony Medina

Makeup: Porsche Cooper

Manicure: Jolene Brodeur

Art Director: Erin Hover

Set Designer: Production Design by Bette Adams / MHS Artists

Bookings: Special Projects

Videographer: Sam Miron