Sam Bailey
Photo: Alexus McClane

Has there ever been a better time to be a black female content creator? Conventional logic would say no; after all, filmmaker Ava DuVernay just inked a $100 million dollar deal with Warner Bros., while Shonda Rhimes has moved her evolving empire of successful series to Netflix in a deal reportedly worth $150 million. And as the narratives of proven hitmakers like Issa Rae and Lena Waithe grow in prominence, so too does the demand and opportunity for fresh new perspectives that explore what it means to be black in America—specifically, a black woman.

But new opportunities are only the tip of the iceberg for creatives of color, who are just beginning to be afforded seats at the table in industries that continue to grant them access with extreme rarity.

One of those emerging creatives is director, producer, writer, actor and 2018 Root 100 honoree Sam Bailey, whose ascent from web series creator to one to watch within the television and film industry has been nothing short of incredible. Until four short years ago, the Chicago native was primarily an actor, continually frustrated with being relegated to “filler roles” in her local theater scene.

“In theater, we used to call it ‘acting in the blackground,’” she laughingly told The Glow Up. “They were like, ‘Oh look, we’re so progressive, showing these faces.’” she continued. “But to me, none of it means anything and representation is all for naught if it’s not about showing all of the humanity of that character.”

Bailey’s dissatisfaction with the amount of well-developed roles for black women led her to create and star in her own webseries, You’re So Talented, chronicling the adventures of Bea, an out-of-work actor in her mid-twenties (who also happened to be a black woman), trying to navigate her way through a quarter-life crisis without a clear sense of direction.

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Sam Bailey starred as Bea Freeman in the first web series she created, You’re So Talented.
Screenshot: You’re So Talented (Vimeo)

It was an incredibly relatable premise; so much so that the series took off, earning a premiere slot at the 2015 Tribeca Film Festival, as well as a Gotham Award nomination. It also laid the groundwork for Bailey’s next web-based project, Brown Girls.

In collaboration with writer Fatimah Asghar, Brown Girls explores the power of friendship between two women of color as each grapples with revelations about queerness, commitment, and career paths. The series, which debuted in early 2017, earned the duo a 2017 Primetime Emmy nomination for Outstanding Short Form Comedy or Drama Series—and a development deal with HBO.

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If the trajectory sounds familiar, it should. Issa Rae traveled a similar path en route to her HBO deal, minus the Emmy nomination (which finally came this year). And the comparisons don’t bother Bailey, who considers Rae and Waithe among the trailblazers who have made her own rise possible.

“I one hundred percent think and know that I am of the lineage of these women—specifically, Issa, but also Numa Perrier and all these women that were making web series about our experiences as black women,” Bailey told us. “That was the first time that I was able to connect creators to content, and realize that women of color could also be behind the scenes, and that the only way we were going to get stories told that interested me, really, was if we were the ones telling those stories. So, because of that, I was incredibly empowered to make my own stuff. ...

For me, that was a really dope experience, to come into Hollywood just after they’d kind of opened up that door a little bit more,” she continued. “And then, I hope to be able to continue to do that for younger women looking up to me, because I just think it almost feels like there’s no world where anyone else is going to open those doors for us. We just have to do it. We have to make our own opportunities, and that’s kind of what I learned watching Issa, and Lena, and Numa, and all these women who I just think are at the forefront of making their own work.”

The TRiiBE

Based in Los Angeles, Ca., Bailey, 29, is enjoying a type of rise and recognition rarely achieved by self-taught directors such as herself. And in an industry well-known for telling creators of color that there’s only room for one at a time, Bailey’s inspired by the crop of collaboratively-minded creatives of color coming up alongside her—and not at all discouraged by the idea of entering another black millennial female narrative into the HBO lexicon.

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“The idea that there can’t be two stories about black women that are different is wack to me,” she laughed. “There are a billion white stories on HBO. Why can’t there be two stories about women of color?”

Brown Girls is still firmly in the development stages at HBO, but in the meantime, Bailey’s adding to her resumé, including directorial credits on Freeform’s Alone Together and several episodes of the upcoming series adaptation of The First Wives’ Club. She’s also close to closing a deal to develop and direct her first feature, a tremendous feat for a director only four years into her career. As for her lack of film school training, Bailey hasn’t let it hinder her progress—or her confidence.

“The film stuff, I learned by being on [camera]; I learned by doing,” she told us. “But I know people. I know what makes people tick ... the psychology of a human is stuff that you learn as an actor. That’s the stuff that I think is difficult to learn. The other stuff comes from doing—and making a lot of fuck ups. But that human thing, like, I’ve been training my entire life for it.”

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And again, it’s the entire life of a character that interests Bailey, who paraphrases Viola Davis when she says: “I just want that regular ass black woman. Like, if we don’t get that, then what are we doing?”

“And I agree, because we’re not sinners and we’re not saints either, right? We’re actually like, fully evolved, complex humans,” Bailey continues. “And that’s what I’m trying to explore, in terms of my work. I’m trying to explore women of color and queer people and all those identities, but specifically, the vulnerability within black women, because [it feels like] we’re either superheroes, or we’re like trash—there’s no in-between. And if you’re a superhero, then you can’t be vulnerable, and if you’re trash, you’re not human.”

“So like, I feel like that kind of stuff is what I’m trying to combat in my work; like, how do you show a fully complex, messy individual? And I believe that if we don’t do that, then we’re really missing out on a huge section of storytelling ... I think that it is imperative that black people get to do everything, and that black people get to be everything, and I still think that we’re not fully there yet.”