It’s a humid night in New Orleans, and Issa Rae’s publicist has invited me to an exclusive nineties-themed dance party. Immediately after I enter the dimly lit room, I notice a woman in a fitted mustard-yellow dress, dancing like she doesn’t have a care in the world. It isn’t until I get closer that I realize I’m watching Rae as she gets her life to the old-school R&B bumping through the speakers. I’m surprised by the public display; everything I’ve read about the 33-year-old Insecure cocreator is that she shies away from being the center of attention. I also can’t stop staring.
What I learn over the course of my weekend with Rae—we meet in her hotel room the morning after the throwback turn-up—is that she isn’t afraid to make a scene. Not on a dance floor, in a writers’ room, on Instagram, or in a room full of white HBO execs who might not understand her vision. “All I know is who I am,” she tells me. “At the end of the day, all I know is my intentions, and no matter what you take out of context, no matter what pictures you post, I know what I am aligned with. I know what my truth is.”
As a black woman in the entertainment industry (I founded the celebrity news site The Shade Room), I think I speak for most of us when I say that people of color are protective of Rae. What makes her especially precious is that she talks openly about her dedication to representing our culture the way she sees it. “You can always tell when [a black show] feels overly explained. If you’re targeting a specific audience, there’s a shorthand people of color have, where you don’t need to explain it,” she says. “If a story line is funny to me, if it’s real to me, if it moves me, then it’s my thing. It’s my experience, so no one can take that away from me.”
Rae’s own story began in Los Angeles, where she was born. (Her father is a doctor from Senegal; her mother is a schoolteacher from Louisiana.) The family detoured to Potomac, Maryland, until Rae was in sixth grade, when they moved back to Southern California, to View Park. “There was a certain age where I was like, ‘I know I’m the shit,’ ” she says of that time. “And then it was middle school where I was like, ‘Oh, I’m not attractive to other people. The guys I go after don’t see me that way.’ ”
Rae became interested in theater while attending the King/Drew Magnet High School of Medicine and Science, where she nabbed the lead in the school play four years running but never saw girls like her in the music videos and movies she studied religiously. “You learn that a very specific type is appreciated,” she says. “For me, it was like, ‘If I want to pursue acting, I know that I am going to always have to be the best friend.’ ” In 2007 she graduated from Stanford University with a major in African and African American studies and a minor in political science.
An early web series she wrote satirized her experiences at the prestigious university, but it wasn’t until her popular 2011 YouTube series, The Misadventures of Awkward Black Girl, that she put herself in a lead role. “The friend that I wanted wasn’t available,” she says. “I was like, Fuck it. I know how to act this part.” Still, she was uncertain about her future in entertainment. “The embarrassment came from making a YouTube series while all of my friends were being doctors, lawyers, diplomats, all of those different things. Those postcollege questions—did I have to go to college to do this? Did I have to pay hundreds of thousands of dollars to make YouTube videos?—that was embarrassing for me.”
“I don’t feel as naive as I once was. I’m way more confident in what I bring to the table now.”
The self-doubt dissipated “when I started making the money back,” Rae says, so she leaned in to the image of the relatable (occasionally embarrassed, occasionally awkward) black woman. Gone are the days of the video girl as the sole arbiter of our femininity. “There was no blueprint to do this. There was no one I could look to to be like, ‘Oh, so-and-so made some videos and then had a television show, and then did movies,’” she says. “You kind of just do it.”
Her characters on Insecure are real. They look cute, act wild, and are unapologetically black while doing it. They also live in a place where black women live. As the backdrop on Insecure, South L.A., and the gentrification that’s transforming it, looms large. “White people left the neighborhood, there was white flight, and now they’re coming back and pushing us out,” Rae says. “I’m moving back there—that’s what I want—but I’ve already seen the change. It’s disheartening.”