Issa Rae Built a Hollywood Career on Her Own Terms. Next, She’ll Build an Empire

The YouTube and HBO star is as talented as she is ambitious

Photography by Chris Loupos for Adweek

It’s a Friday afternoon in late August, and Issa Rae—the creator, star and executive producer of HBO’s Insecure—is leaving the bar at The London hotel in midtown Manhattan. But before she can make her way back to her room, a nervous woman stops her. Apologizing, the woman says that she never asks celebrities for photos, but on this particular occasion, felt compelled to make the effort.

Styling: Jason Rembert; Hair: Felicia Leatherwood; Makeup: Joanna Simkin

A few moments later, after Rae has obliged the selfie request with a wide grin and left to get ready for a party for Insecure’s Season 2 soundtrack, the woman explains: Rae, she says, is “a hero for women 25 and up with melanin.”

Rae, 32, didn’t find this kind of recognition overnight. Sure, she created a beloved YouTube show in 2011 that was viewed by millions (Awkward Black Girl), landed a deal with ABC and Shondaland in 2012 (the network eventually passed on her show, I Hate L.A. Dudes) and in 2015, published a New York Times best-selling memoir (The Misadventures of Awkward Black Girl). But she’s also dealt with development hell: while with ABC, Rae says, she was unsure of the story she wanted to tell and overly eager to please executives, leading to “a mushy, generic script.”

After the ABC deal ended, HBO called Rae to tell her they liked her YouTube show and wanted her to pitch something in that vein. She did, creating Insecure, a half-hour comedy that follows “Issa Dee” and her best friend Molly as they deal with dating and job struggles in Los Angeles. HBO ordered a pilot in February 2015, and the series premiered in October 2016.

The response was huge. Insecure became a critical darling, landing Rae a Golden Globe nomination and drawing famous fans like Oprah Winfrey and Michelle Obama. And HBO clearly wants to see it succeed: this summer, the network put Insecure in the time slot directly after Game of Thrones, boosting the show’s audience to 1.3 million viewers in August.

Rae hasn’t become complacent, though, spouting off a long list of things she still wants to accomplish. “I want to be able to create movies. I want a television channel. I want a studio. I want various media arms. I want to have political influence,” she says. “I want to do so many different things. I want to figure out how and the best way to use my voice.”

People are certainly listening. A few weeks later, during a red carpet interview at the Emmy Awards, Rae said that she was “rooting for everybody black.” The comment made headlines, inspired a New York Times op-ed and was emblazoned on T-shirts. And when news came out that she had inked a deal with CoverGirl, her fans cheered her on.

“To be a CoverGirl is something I never thought possible,” Rae explains via email after the deal is announced. “Only in my adult life have I learned to be comfortable in my skin, so if I, as an ‘awkward black girl,’ can become [a CoverGirl], it sends the message that anyone who is feeling insecure in their own skin can and should be celebrated as well.”

With that kind of hyper-awareness, it’s easy to see why Rae would be chosen to champion a brand like CoverGirl, especially as the brand is looking to be more inclusive and reflective of its consumers in its marketing. (See below for a sneak peek of the new CoverGirl work by Droga5 featuring Rae. A 90-second spot showcasing the new brand positioning will be released tomorrow.)

“I really identified with their new branding: ‘I am what I make up,’” Rae says. “As a creative who has built her career from the ground up, those words really resonated with me.”

Rae doesn’t have to build everything for herself anymore. Nowadays, it’s Hollywood that’s courting her. In August, she starred in the music video for Jay-Z’s “Moonlight.” She also landed her first major film role (in an adaptation of the best-selling YA novel The Hate U Give) and is penning a few scripts, including one for a Netflix movie set to be directed by Ava DuVernay and starring Rihanna and Lupita Nyong’o.

“My career started because I had something to say about what I wasn’t seeing,” Rae says. “Me vocalizing what I wanted to see, it basically changed my life and I’d say even the course of representation indirectly. And I want to see what else I can do just by speaking up and speaking out.”

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