Andra Day Took 2 Years Off Music to Focus on Her ‘Terrifying’ Role as Billie Holiday

It’s not uncommon to see our favorite, multi-talented stars make the leap from one medium to another. Actors become directors, dancers become choreographers, and comedians become voice actors.

Sometimes, the voices that dominate our playlists will suddenly manifest on-screen, as singers bring the emotion they pour into each song to Hollywood. It makes sense — singers already have powerful voices, incredible stage presence, and an intense work ethic.

On paper, R&B artist Andra Day had all the qualifications for acting, but her very first role would test her in unexpected ways. 

Andra Day rocketed to R&B stardom

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Day’s very first album debuted in the top ten of the R&B and hip-hop genres, according to All Music. At 29e years old, Day took many listeners by surprise. The record, “Cheers to the Fall,” was many fans’ first introduction to Day, yet it featured a star-studded list of features and an unforgettable voice. 

As it turned out, Day’s big break was a long time in the making. From a young age, she enjoyed singing at church and had a passion for the creative arts.

Andra Day posing on the red carpet floor
Andra Day | Kevork Djansezian/Getty Images

Her captivating performances attracted large audiences. One such crowd featured Kai Millard Morris, who was the wife of Stevie Wonder at the time. This connection opened up an expansive network of powerful figures — all of whom fell in love with Day’s soulful style. 

Thanks to a built-up YouTube following and undeniable talent, Day was able to sign with a record label in 2011. She would eventually partner with Warner Brothers to release “Cheers to the Fall,” her 2015 debut that featured such hits as “Forever Mine” and “Rise Up.” 

Day has lent her talents to TV and film

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Understandably, Day’s music was in high demand following her first album. As IMDb documents, “Rise Up” was quickly the soundtrack to some of the time’s biggest shows — from Grey’s Anatomy to The Blacklist. 

In 2017, she took her talents to the set of Marshall, a hard-hitting documentary made even more emotional through her performances. Her rendition of “Stand Up for Something” was worthy of a standing ovation. She would give an encore performance at the Oscars just one year later, where she was nominated for an Academy Award. 

Over the years, Day has continued to rack up royalties. Her songs play in the background of some of our favorite on-screen worlds. Her listed filmography has grown quite extensive, although she is mostly credited as a member of the soundtrack.

She’s performed on late-night talk shows, singing competitions, and even tried out voice-acting for Pixar’s Cars 3. Still, her biggest on-screen role — and biggest challenge — didn’t come until recently. 

Her on-screen debut as Billie Holiday was taxing

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Day was presented quite the challenge when she was encouraged to audition for the lead role in The United States v. Billie Holiday. The movie tells the story of Billie Holiday, a talented 30s singer who was relentlessly persecuted by conservative authorities. Holiday, who struggled with addiction and frequent arrests, is a complicated character that has previously been tackled by the likes of Diana Ross in Lady Sings the Blues

According to Harper’s Bazaar, Holiday was a large inspiration for Day. Honoring her life and legacy came with a lot of pressure. Day went on to tell the Los Angeles Times that the role was downright terrifying to her — in more ways than one. 

“First of all, I’m a fan of hers. And I’ve always loved movies and had such a great respect for the craft of acting,” she confessed. She didn’t know if her movie debut could do either justice. Fortunately, the film process was lengthy — with Day landing the role in 2017 and wrapping in 2019. The singer used the time in between to dive into her role, adopting some of Holiday’s habits and inadvertently dabbling in method acting. In the end, Day says that “the role changed [her].”

Despite her tremendous fear, it’s clear that Day was successful in the role. In fact, her Los Angeles Times interview was part of a roundtable discussion — one that she earned her place at by being nominated for an Oscar.