Issa Rae Is Building an Empire

The ‘Insecure’ creator says she wants a “super career” like Oprah or Ellen—and she’s well on her way

It’s the Sunday just before Christmas, and Issa Rae is working, getting glammed up for yet another photo shoot—the fourth of her week—in the sprawling two-story office space she recently bought in Inglewood that serves as headquarters for Issa Rae Productions. Surely she’d prefer to be thinking about her up-coming vacation in France, but these days she’s cramming in a lot.

In February the 34-year-old plays the lead in The Photograph, a romantic drama written and directed by Stella Meghie and coproduced by Will Packer (Girls Trip). Later this year Insecure, the hit HBO show she created, writes, and stars in, returns for its fourth season. In April she’ll costar opposite Kumail Nanjiani in The Lovebirds, a rom-com from Michael Showalter that she rewrote and executive produced. Last August A Black Lady Sketch Show, the groundbreaking program she executive produces, was renewed for its second season by HBO. And her production company, which inked a deal with Columbia Pictures in December 2018 to promote diverse talent, has a wealth of projects in development, including Badmash, a Bollywood crime comedy, and Perfect Strangers, a remake of the award-winning Italian movie about a dinner party that goes awry when friends reveal what’s on their cellphones.

“I love working. I just do,” says Rae, who was born in Los Angeles and spent much of her childhood in Inglewood and View Park-Windsor Hills.

And then there are her projects outside of film and TV. She’s launched her own music label, Raedio, which in October signed with Atlantic Records. She was a recent face of CoverGirl. She’s a voice for Google Assistant. She just partnered with Hilltop Coffee Partners to open a café in Inglewood, one of her many efforts to give back and build community. And she’s an investor in Streamlytics, a streaming-media data startup from Angela Benton, known for her efforts to bring diversity to tech.

When Rae is asked if she’s looking to emulate anyone’s career, the Stanford grad has several one-name examples at the ready: Oprah, Diddy, and Ellen. “[They] kind of embody the super career that I want,” she says, praising the entertainment empire Oprah built and her vast influence, Diddy’s business acumen, and the manner in which Ellen DeGeneres has turned her wacky personality into a successful brand. “She’s been authentically herself her entire career, and that’s how I want to be as well,” she says of DeGeneres. Rae concedes that she’s heard the rumors about the daytime TV host being difficult to work for but says, “She’s been great when I’ve talked to her.”

Rae first gained acclaim with the web series The Misadventures of Awkward Black Girl, and her best-selling book of the same name, but The Photograph finds her in serious dramatic territory. She stars as a young woman grappling with her mother’s unexpected death—and an unexpected romance. “I was just really attracted to playing someone of a different mind-set than myself,” she says. “It was a bit intimidating.”

In The Lovebirds she returns to her comedic roots. Shooting in New Orleans, she and Nanjiani bonded over their shared love of eating and body obsessions. “I’ve never met a guy where we share like food passion and like crazy diet passion,” she says of her costar, who recently stunned fans with a photo of his dramatic hard-body transformation for the upcoming Marvel flick Eternals. “I’m a big crash-diet person—I will try anything to lose weight,” says Rae, who’s done everything from the Master Cleanse to the peanut butter diet. Rae says Nanjiani was slimming down and bulking up for Eternals as they were shooting. “There was a period where his transformation allowed him to eat like 3,000 to 4,000 calories a day,” she recalls. “He would constantly rub it in my face like, ‘Oh, I’m just gonna eat dessert.’”

When asked about what fans can expect with the new season of Insecure, Rae is vague, revealing only that it deals a lot with growing pains, but viewers can take comfort in knowing that she’s planning a fifth season “if HBO will allow it.”

As her star rises, Rae says the challenge is living up to the increasing hype surrounding her. “When people don’t know you, nobody expects anything.” When she was first coming up in the industry, she sometimes struggled to get people interested in her and stories about black women, now the opposite is true, and she worries about being a passing trend. People “just want to be able to say that they have you. … Right now, that is the hardest part,” she says. “And that’s a different problem [from what] I had five years ago. No one was checking for us. Now when everyone’s checking for us, what’s the intention?”

Despite her success, Rae says she’s still awkward. Recently she was in Mexico and someone complimented her on her braids. As she said thank you and touched her hair, a braid fell out in her hand. “I put it in my purse and just kept pushing,” she says with a laugh. “This is my life.”

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