YouTube Sensation Issa Rae Is Making Moves To HBO

"I attract people who are the same, so they get it"

Photographed by Natalie O'Moore. Styled by Ayanna James.

The following feature appears in the October 2016 issue of NYLON.

“I’m a boring person all day, and that will never change,” says Issa Rae with a laugh. The writer, actress, producer, and voice behind the YouTube sensation The Misadventures of Awkward Black Girl may be right, but from the outside looking in she’s anything but. Casually dressed in jeans and a T-shirt with the word “Inglewood” emblazoned across the chest, she sits down to chat in her Los Angeles office, which looks a lot like your best friend’s apartment, right down to the hot pink paint. “My favorite thing to do with my friends is to sit and talk about nothing, just like this—in their home, in my home, in a restaurant—it’s the best,” she says.

While millions already know Rae from her internet series, or as the author of the eponymous New York Times best-selling book it spawned, her fan base is about to blow up in a very big way. This October, HBO will premiere Rae’s new show, Insecure, which follows its main character—played by Rae—through the struggles of everyday life. Like Awkward Black Girl, the show hinges on Rae’s honest, observational humor, immediately relatable insecurities, and fumbling attempts to just be chill.

Growing up the middle child of five in Maryland, then Los Angeles, Rae says a lot of her work stems from her family, and from her experiences trying to fit in as a young black woman. “My whole upbringing was just me trying too hard,” she says. She wrote throughout junior high and high school, but didn’t catch the acting bug until college. “When I was a freshman this one girl wrote, directed, and produced her own hip-hopera,” she says. “I saw the work that she put into it and I saw what came out and I was like, ‘Wow, this is cool, and she’s only a couple of years older than me. She did this, and I want to do this, too.’ That caused me to produce and direct plays, which led to the first web series.”

Click through the gallery to read the rest of this feature.

Shirt by Bridget Awosika (available at, jeans by Topshop, earrings by Sara Designs NYC (worn throughout).