Andra Day May Have Landed the Role of a Lifetime, But She's Only Just Begun


The second you press play on The United States Vs. Billie Holiday, our cover star Andra Day’s acting debut, there’s a feeling so visceral you can almost hear it. You could call it magic, but if you watch the film, you’ll realise "magic” is far too cliché and syrupy of a word to accurately describe Day’s Golden Globe–winning, Oscar-nominated portrayal. Instead, it’s a feeling akin to a sound you might hear at a baseball game, the reverberating crack of wood colliding with cowhide, a grand slam that no one, Day included, really saw coming. Of course, The United States Vs. Billie Holiday is a success in the literal sense. The film has captivated audiences and received nationwide critical acclaim since its February 26 release on Hulu, but there’s another layer to this particular moment. Not only does the film reveal jazz legend Billie Holiday’s true 360 legacy (shedding light on intimate, complex sides of the singer that fans may be unfamiliar with), but it also unveils untold American history.

As the first moments of the movie unfold, a chilling melody is made more somber by a caption recalling the United States Senate’s 1937 failure to pass a bill that would ban the lynching of African Americans. Then, a direct cut reveals Day poised as Holiday onstage, dripping in a glittering silver Prada gown, shoulder-scraping diamond earrings, and the singer’s signature: a flower, precisely pinned just above her ear. Aesthetically, the image is enough to sweep you off your feet and transport you to Holiday’s three-decade era of artistry, but it’s Day’s piercing gaze and vulnerability that will keep your attention—for the duration of the film, yes, but also for everything Day has in store for us as a singer, actor, and "servant of God.” As I quickly discover over the course of our 37-minute conversation, the latter is intrinsically connected to Day’s spirit, and in her eyes, it just might be her most important role to date.


(Image credit: Lauren Crew; Styling: ALIÉTTE dress; T Label gloves; Made by Malyia earrings; Grace Lee rings; Giuseppe Zanotti shoes)

Although some might consider Day an activist (her chart-topping single "Rise Up” has become the unofficial anthem for Black Lives Matter, for instance), it’s not actually a term she identifies with. "It’s so funny to hear the word ‘activist’ because I don’t think of myself as one,” she chuckles. "I know that people would say that probably sounds very cliché and humble-but-not-humble, but I don’t. I want people to know that I love God, and I want people to encounter that when they encounter me. These ascribed titles, I don’t give them to myself, and, you know, Billie didn’t either. It’s just wanting to help people and wanting to serve more than anything. I’m a servant. That’s what it is, and that’s the best way I can describe it. In my mind, I have this beautiful picture of eternity, just regarding each other as higher than ourselves and everybody is loved and valued and taken care of.”

God, Day tells me, was also one of the main reasons she decided to audition for her now award-winning role—a role that, initially, both she and the film’s director, Lee Daniels, felt she had no business having anything to do with. Despite Day’s longtime love for Holiday, which dates back to her preteens, she had no professional acting experience. She didn’t have any acting experience at all other than her early years spent at a performing arts school doing musical theater. "I always knew I wanted to be involved in the arts and to perform, but back then, it was more about ‘Well, do I want to try to do Broadway, or do I want to try to record music?’” Never, she says, would she have ever believed she’d be up against Hollywood’s elite acting talents for the industry’s most coveted awards. "I mean, I didn’t want to do this movie. I was terrified. I was like, ‘I’ll go through with the audition, but I’m going to be terrible.’ Lee and I, we were kind of forced on each other,” she laughs.

"But then we started talking, and when I found out the film would focus on the Federal Bureau of Narcotics and how Harry J. Anslinger, J. Edgar Hoover, and [Joseph] McCarthy created this targeted war on drugs to get Billie to stop singing ‘Strange Fruit,’ a song about lynching in America, I realised that this film would be vindicating her legacy. That was extremely enticing for me. That’s what made me audition.”


(Image credit: Lauren Crew)


Day was also struck by Daniels’ devotion to telling the truth and introducing a layered, dynamic woman from decades ago to today’s audience. Those two words—"layers” and "truth”—could be Day’s through-line when it comes to women who inspire her. There’s Holiday, of course, but there’s also civil rights icon Angela Davis, whom she portrays in the music video of her latest single "Tigress and Tweed.” "I’m drawn to fierce, strong, Black women,” she muses. "And not just for our fight. We are fierce and strong in so many different ways. I think it’s interesting when people think femininity is very delicate and soft. I mean, femininity is super strong! There are layers to us, and we are all different. I like to see us in spaces where, traditionally, we haven’t been represented.”

I pose the question that perhaps it’s those historical influences she’s drawn to and her obvious dedication to truth that have driven the decisions she’s made professionally. She agrees, replying that more than anything, she strives to communicate truth through her work. "I’m a deeply spiritual person. There are a lot of loud voices in this space right now, and I just don’t understand sowing seeds of division. That is not how I’ve encountered God. I think that when it comes to equality among races, equality among genders, these are systems of inequality that have been built on deception and lies. If you’re going to allow systems like that to persist and grow, you have to control and manipulate the narrative. I think the only thing that can dismantle a system of deception, obviously, is a healthy dose of truth. And I think people need to understand the intentionality of inequality. It’s not just ‘oopsy-daisy, it happened like this.’ No. It’s something that’s been built up.”


(Image credit: Lauren Crew; Styling: Ellery top and pants; Aralda Vintage earrings; Giuseppe Zanotti shoes)

Despite the buzz and inarguable triumph of her first-ever professional acting job, Day sits on the other side of a screen from me via Zoom, remarkably unaffected by her own success. Though emboldened to continue this new acting trajectory, she confesses with a refreshing unguardedness that she’s still consistently seized by fear. "I guess there’s an official name for it now: imposter syndrome. I have the biggest case of it. Even now, as we’re speaking, I go into all of these interviews and everybody’s exclaiming how great I am, and in my head, I’m just like, they don’t really know. I think it’s something, in particular, that we, as women, really struggle with, and then to another degree, we, as Black women, deal with. I think humility is a strength and a fuel, but those feelings of insecurity and inadequacy—that unworthiness, this imposter syndrome—that’s what I’d like to see rooted out.”

Day is still grappling with how exactly to proceed as normal after eating, breathing, and sleeping all things Billie Holiday for three full years. In fact, when I ask her what the detachment process has been like—how one unsticks themself from a figure of that caliber—Day responds without a moment’s hesitation that she’s still, quite honestly, trying to figure that part out. "Prayer has been a huge part of trying to find that place of balance again and identifying who I am and who I’m supposed to be in this particular season. There are aspects of Billie that will never go away, and there’s a large part of me that doesn’t want her to. I’ve been here for three years, and then all of a sudden, it’s like, ‘Okay, go be you now.’ Therapy is not a scary word for me. After all the press is over for this, I am going to go talk to someone to make sure everything is copacetic up here,” she laughs as she taps her caramel-brown curls.


(Image credit: Lauren Crew)


That’s not to say Day will be taking much time away from the spotlight, though. Just weeks before we spoke, "Tigress and Tweed,” the first single from her upcoming album (mark your calendars for June 4), hit the stratosphere, and her portrayal of Angela Davis in the music video will give you chills. Additional singles from the album will hit in April, and Day beams as she shares the details, adding that there will definitely be some "Billie DNA” injected into the project. "I want to tell stories, and I’m actually developing something right now and just praying about it because hopefully, I don’t suck at this,” she laughs. "I just have to remind myself that, hey, it worked last time. Let’s, you know, let’s keep believing in yourself.”

If you take a look at Day’s past red carpet moments or soulful clips from her performances onstage, it immediately becomes clear just how much history has impacted her approach to fashion and beauty as well. Even before her portrayal of Billie Holiday on the big screen, you’ll notice subtle and not-so-subtle nods to retro glamour and old-school flairs of jazz and blues woven through her fashion, hair, and makeup choices. "I am hugely inspired,” she nods. "I’ve always been sort of a vintage girl, and I just love the style—Dorothy Dandridge, Pearl Bailey, Billie Holiday. It just seems like everything was done with so much more detail and intention. The structure and the craftsmanship and, you know, just the drama of it all. It was so beautiful, and so I do kind of live in that world in my head,” she smiles.


(Image credit: Lauren CrewArea headpiece and dress; Commando bra and brief; Christian Louboutin shoes)

To be clear, however, that’s most likely not how you’ll see Day pull up on a day-to-day basis. Though she’s remained fiercely loyal to her longtime glam team featuring makeup artist Porsche Cooper, hairstylist Tony Medina, manicurist Jolene Brodeur, and stylist Wouri Vice (all of whom she lovingly calls her family), most of the time, she says, you’ll catch her in a basketball tee, sweats, hair uncombed, and legs and armpits more likely than not unshaven. "I’m so lazy when it comes to my look. And that sounds so bad, but I think that definitely makes the moments when I’m dressing up so much more fun and special. I have two different sides: glowy effervescence or vintage vixen meets evil Disney villain. But the reality is, sis, in my regular life, no. If I have the time and I’m not lazy? Then, yes, she a vintage little squirrel.”

As Day and I are chatting about our mutual love for sweats and going sans shave, she makes me laugh so hard I quite literally choke on my last question. "Don’t worry—I’m the queen of awkward,” she assures me. When I catch my breath and finally form a sentence, I ask Day about the societal pressures to look and present in a certain way. She immediately offers her advice for anyone struggling to feel empowered, beautiful, or comfortable as their most authentic self. "You know, I believe that every single one of us was created with intention, with purpose. Every single person is beautiful. We have to remember that most of us, at least here in America, view ourselves through the lens of this white, male, straight patriarchy. I think it really comes down to unlearning everything that’s viewed through that lens and understanding how limiting it is. And also, it’s important to remember there is only one us. Erin, is that how you pronounce your name? There is only one Erin, and there has never been another Erin; there will never be another Erin. And when you think about that, you're just like, ‘Damn. When I am gone, that’s it.’ Clearly, we are beautiful and designed with intention.”


(Image credit: Lauren Crew)

As we wrap up our time together, Day seems to make her intention as an actor, singer, and truth-giving servant just as clear. That narrow little lens we mentioned? She’s here to remind us that it’s "too super-duper small” and "too super-duper not true.” Andra Day has a message for us all: There is only one you, and you are the most valuable commodity. 


(Image credit: Lauren Crew)

The United States Vs. Billie Holiday is now streaming on Hulu.


Photographer: Lauren Crew

Stylist: Lauren Eggertsen

Hair Stylist: Tony Medina

Makeup Artist: Porsche Cooper

Manicurist: Jolene Brodeur

Creative Director: Cassandra Lear

This story was originally published on Who What Wear US.

Beauty Director

Erin has been writing a mix of beauty and wellness content for Who What Wear for over four years. Prior to that, she spent two and half years writing for Byrdie. She now calls Santa Monica home but grew up in Minnetonka, Minnesota, and studied writing, rhetoric, and communication at University of Wisconsin, La Crosse. She studied abroad in Galway, Ireland, and spent a summer in L.A. interning with the Byrdie and Who What Wear family. After graduating from UW, she spent one year in San Francisco, where she worked as a writer for Pottery Barn Kids and PBteen before moving down to L.A. to begin her career as a beauty editor. She considers her day-to-day beauty aesthetic very low-maintenance and relies on staples like clear brow serum (from Kimiko!), Lawless's Lip Plumping Mask in Cherry Vanilla, and an eyelash curler. For special occasions or days when she's taking more meetings or has an event, she'll wear anything and everything from Charlotte Tilbury (the foundations are game-changing), some shimmer on her lids (Stila and Róen do it best), and a few coats of the best mascara-type product on earth, Surratt's Noir Lash Tint.