Issa Rae from HBO's 'Insecure' poses for a portrait at the 2016 Summer TCAs Getty Images Portrait Studio at the Beverly Hilton Hotel on July 27th, 2016 in Beverly Hills, California
Maarten de Boer—Getty Images
By Daniel D'Addario
September 1, 2016

“I want to make this very clear,” Issa Rae says as she describes Insecure, the HBO comedy she created and stars on. “This is not the quintessential black-woman experience. It’s a very specific experience.”

The emphasis is unnecessary. Rae, whose popular web series The Misadventures of Awkward Black Girl and memoir with the same title helped establish her as a rising star, has no trouble getting her points across. And her show, based in large part on conversations between Rae and her real-life friends, crash-lands into a TV landscape where there are finally more than a few nonwhite characters who are not just tokens. Insecure, which premieres Oct. 9, is about as far from a generic idea of the “black-woman experience” as it gets.

Rae’s character, also called Issa, shares a sharp wit with her creator but lacks direction in work and in her relationship. “She’s me if I didn’t know what I wanted to do,” says Rae. Working at a nonprofit for inner-city kids, Issa—the character—is fatigued by her white co-workers, who treat her with a mix of condescension and curiosity. “Issa,” one asks, looking for a definition, “What’s on fleek?” She shares a close but at times uneasy friendship with high-flying corporate lawyer Molly (Yvonne Orji), and seems to stay in her relationship with live-in boyfriend Lawrence (Jay Ellis) more out of inertia rather than love. Both serve to remind her that she’s not getting what she wants out of life.

It’s a surprising vein to tap into for a person who’d appear to be in among Hollywood’s more enviable positions. How does one make a show all about youthful unsteadiness—less about the fear of failure than the active knowledge one is failing—when, with your own half-hour on HBO, you’re closer to superstardom than most could dream? But Insecure hasn’t dispelled insecurities for Rae, who notes that her YouTube start is seen as “kind of lowbrow.”

You didn’t come up the traditional way—you kind of broke in, is the perception on many fronts,” she says. “When I’m in a room with the bigger movie stars and the television stars and the people who’ve been doing this for a while… Even though I can call some of the showrunners my mentors, I still feel insecure about my own place in Hollywood.”

Rae had already been through the TV machine by the time Insecure started filming; a past pilot, I Hate L.A. Dudes, which she’d worked on for ABC with Scandal creator Shonda Rhimes, was not picked up. “During that process, I was eager to please and kind of lost my own voice. I wasn’t cemented in my voice in the same way,” she says. (She now works with showrunner Prentice Penny, whose producing credits include Brooklyn Nine-Nine and Happy Endings.)

Larry Wilmore, who co-wrote the first episode before departing to host the recently-cancelled Nightly Show, recalls being surprised at their first meeting. “I loved the fact [that] she’s an entrepreneur—she did it on her own. And then when I met with her, I was even more pleased. I couldn’t believe how mature an artist she was for somebody who was supposed to be green.”

What’s perhaps most surprising about Insecure is its assertive specificity. This is not the work of an artist willing to compromise or lay out a road map to welcome viewers in; it’s a show whose laughs are built on just how well its creators understand its South L.A., hip hop-inflected milieu not often seen on TV. Rae’s character raps into the mirror as well as onstage, mocking Molly’s “broken pussy” in an incendiary freestyle; the students she tepidly tries to help berate her.

“I always talk about Curb Your Enthusiasm,” Rae says. “I’m not Jewish, and there’s a lot of stuff that’s [culturally] specific to that show that I didn’t get, that I had to look up! And that’s fine—I still enjoyed the show. I feel that way about our show.”

It’s an interesting comparison, and not the expected one, to the semiautobiographical current HBO series created by and starring a young woman. (Rae also compares her show to Entourage, saying she hopes it does for South L.A. what the bro-centric comedy did for Beverly Hills—another unexpected comparison.) But if Girls‘s title and early episodes positioned the show as something of a statement about an entire generation, Insecure leans from its first moments away from archetypes and into character.

As a result, political or cultural flashpoints that find their way into the work—like Molly’s code-switching, shifting effortlessly from corporatespeak to, with Issa, more relaxed vernacular—seem to arise organically. “I didn’t think, ‘This is an issue plaguing the community that I want to address,’ any more than anybody else did,” Rae says. “What’s refreshing about this time is that because there are so many other shows with creators of color, the onus isn’t just on us. That’s a great thing.”

Those shows include black-ish, Scandal, and Empire, as well as upcoming fall shows Atlanta (created by Donald Glover for FX) and Queen Sugar (Ava DuVernay for OWN). While all depict the black experience, none are solely about being black in the tokenistic way of TV history. All feature characters who are people first; viewers who can’t get past that are doomed to miss out.

Still, core HBO viewers staying tuned after the upper-middle-class comedy of manners Divorce might experience whiplash. “Her landscape is not crowded right now. In the world of HBO, Showtime—there’s nobody doing what she’s doing,” says Wilmore. “She gets to stand on her own, which is fantastic.” It’s an opportunity, and a challenge: Rae is blazing a trail on premium cable.

But if anyone has the motivation, it’s a writer for whom bootstrapping a YouTube series isn’t far in the rear-view mirror. Rae says the possibility of being pulled back to a cubicle still drives her. “I’m still, to a degree, scarred by the stuff I hated about working a 9-to-5,” Rae says. “Any time I feel like getting lazy or procrastinating in my current situation, I always think back to that. Bitch, do you want to still be at that 9-to-5? And I act right.”

Contact us at editors@time.com.

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