Billie Holiday Star Da’Vine Joy Randolph Is On A Mission To Tell Un-Google-able Women’s Stories

The United States vs. Billie Holiday tells the very Googleable story of jazz singer Billie Holiday being hunted by the federal government in repeated attempts to bring her down on drug charges. As your search might tell you, this obsession with Holiday was less about drugs and more that she was a successful Black woman with something to say, particularly through her protest song “Strange Fruit." Holiday’s story is harrowing, and singer-actor Andra Day does a fantastic job of channeling her musical predecessor. But there's another, lesser known person in Billie Holiday who you'd probably watch an entire movie about, too: Billie Holiday’s friend Roslyn. The Italian-speaking, eye patch-wearing, dog-sitting, hair-styling, dressed-to-the-nines loyal confidant just has to have her own incredible life story, right? Right?

Sadly, while Roslyn really existed, her actual life story has been lost to time. 

“This is my second time playing a real person,” actress Da’Vine Joy Randolph explained to Refinery29 ahead of the film’s February 26 release on Hulu. The 34-year-old was critically acclaimed for her role in 2019’s Dolemite Is My Name in which she played actor Lady Reed alongside Eddie Murphy’s Rudy Ray Moore, the comedian, filmmaker, and “godfather of rap.” While Moore is remembered in entertainment history, Reed is not.

“Even with Dolemite,” Randolph says, “there were the movies I had that I could watch of hers, but you can't Google her. There’s no way to find her." When she approached Roslyn, show found the same roadblock. "That is a huge problem and part of my found drive to continue to tell these stories, so that you can look these people up, so that you can understand their history. We’ve got a lot of work to do. There are a lot of people that we need to cover.”

Luckily, Randolph did find some information on Roslyn. She knows that she was Holiday’s childhood best friend, the person who knew her the longest out of her entourage, and someone who knew about all the trauma the famed singer faced growing up. She learned that Roslyn “was a bit more straight-laced. She wasn’t into all the drinking and the drugs.” Randolph also notes that the real Roslyn did go blind in one eye and was starting to lose sight in the other. So, the actor made sure to start rehearsing with the eyepatch right away.

“I got to work on it so it looks natural and I don't look like a pirate,” she said. “I didn’t want people distracted.”

But, the most important true life element Randolph was able to reference was the singular photo of Roslyn that was available to her. “Just to see that, I was like, This is a strong, statuesque, solid woman. And this was a real sisterhood.”

Randolph admits it might sound a little trippy, but from there, she says she connected with Roslyn on a somewhat spiritual level to fill in the gaps.

“There’s a point where I feel as though you connect with the essence and the soul and the spirit of the person in a way that then you're kind of guided,” she said. “You have to, at a certain point, surrender and be like, listen, I only know what I know, but instinctually this is what I feel is how they would act or respond knowing the information that I do. At the core, I knew that she had unconditional love for [Billie], like a sister, like a mother, like an auntie, and that by any and all means she wanted to see Billie successful.” With this in mind, Randolph “focused on really being that nurturing almost even maternal figure for Billie, who she had there by her side and at her disposal.”

As far as Randolph knows, Roslyn passed away not long after Holiday died of cirrhosis in 1959. “That was factual that Roslyn stayed by her side,” Randolph says of their lifelong relationship. But, the hospital would not let Roslyn inside to visit her friend as she was dying. “You know how people will say, like, old people will die of broken hearts?” Randolph says. “From my knowledge, I believe that she soon passed thereafter. It was too catastrophic for her.” 

Aside from what she was able to find out about Roslyn's deep connection with Holiday, Randolph was also helped into character with the 1940s costumes she had to wear. These included bras that “were like these cone-shaped death contraptions,” real vintage heels that “were no joke,” and recreations of dresses that were custom-made using actual vintage fabrics. 

“During that time, everything was so coiffed and tailored, it's like the era of the pencil skirt, so you couldn't move much,” Randolph says. “Just hanging out and chilling, you were dressed. You were in a dress. So, it definitely immediately put me in a different posture.”

Whether she’s in ‘40s furs or 1970s sequins, Randolph has found a purpose in telling the stories of women like Roslyn and Lady Reed, who most viewers of Dolemite and The United States vs. Billie Holiday would never have heard of otherwise.

“I think the biggest thing that we see [in the movie] is that, in fact, the world isn't all that different,” Randolph says. “So, how can we now with our voices be activists and what is our ‘Strange Fruit’? What is our call to change and the ways that we can bring about a difference? Because we all have a gift — and it doesn't need to be creative. We were all put on this Earth with a unique gift, and hopefully, in the pandemic you figured out what that was, and if you didn’t,” she adds with a laugh, “continue. Figure out what it is, because that's your purpose and something no one else can do the way you do it.”