First, there’s something you should know:
Most of this takes place in the right-before. Just three days before the city of Austin canceled the South by Southwest festival and, with it, the premiere of Issa’s film The Lovebirds. Just a week before Coachella was postponed until the fall. Just 11 days before Disneyland shut its gates. Just 12 days before Los Angeles closed down restaurants, bars, and gyms to protect people from the spread of you-know-what.
Basically, just nanoseconds before we were all indefinitely confined to our homes, regularly spiraling through the five stages of isolation—anxiety, loneliness, grief, guilt, Instagram-baking—between Zoom calls that assured friends, coworkers, and parents that we were “doing okay, I guess?”
Before all that, it was just…a sunny Tuesday afternoon in L.A.
The scene of Issa’s Cosmo cover shoot at Milk Studios looks almost as on point as an Issa Rae Production. A camera flash lights up That Smile.
A champagne flute sits with the faintest trace of her lipstick staining the rim. There’s a high-powered publicist perched nearby. At one point, the soundtrack switches to Pardison Fontaine’s “Peach” featuring City Girls, and Issa slips out of her smize to mouth along to City Girls’ signature “period.” Everyone else watches and waits, ready to be overly attentive when called upon. It’s obvious that we all get it: We’re in the presence of the leading lady of Hollywood’s current Black Renaissance.
That night, after Issa’s changed out of these in-your-face prints and into a chill Adidas tracksuit, we chat in her office in Manhattan Beach, where she produces HBO’s Insecure (she also writes for and stars in it, in case you’re the one person on earth who needs reminding).
There’s a collection of art leaning against the wall, including a canvas of Spider-Man comic panels. I show Issa the Spider-Man tattoo on my forearm and her eyes light up. “That’s my boo, since third grade,” she says. “I always say that if I ever got a tattoo, it would be a Spider-Man tattoo.”
For the record: Spidey—specifically the ’90s cartoon version where he was a college kid juggling grades, a part-time job, and relationships—was her first love, before he was everyone else’s. “I feel like a hipster,” Issa says with a laugh, “like, ‘Spider-Man was ours!’ And now he’s for everybody.”
Sure, I could ask about how that sense of ownership might connect to the way her own day-one fans feel about her work, but it’s too late. She’s already whipped out her phone and asked, “You fuck with Tender Greens?” Issa knows how to get the setup out of the way. Plus, she likes their hummus.
In the after, a few weeks later, we talk again, this time on the phone, because of course. Issa is “maintaining.” Except for when, earlier, she drove by the Culver City Stairs, the base of a popular L.A. hiking trail, and it was packed with people crowded around food trucks. “What?!” she says (to me, but I imagine her also yelling it to no one in her car). “What is this? Do you all not know???”
Mostly, though, she sounds as casual as she’d been in her office—a side effect, perhaps, of living in L.A., which she describes as having a “Southern laid-backness.” That’s what’s helping her get through this weird in-between we’re living in: between the grief of losing our normalcy and the guilt that follows when we think of those drowning in “real” grief.
Between the urge to be (and document) our most productive selves and the nagging sense that none of it actually matters. Between the heartbreak that comes with the cancellation of the good stuff we were looking forward to—the plans, the projects, the parties to celebrate all the hard work—and the “odd comfort,” as Issa calls it, that comes with knowing this isn’t happening to just you.
After The Lovebirds, a rom-com caper she stars in with Kumail Nanjiani, got pulled from theaters before it even hit them, Issa watched the same thing happen to the rest of Hollywood—projects fizzle or fail to launch, leaving her peers in the “creative collective” feeling lost.
In Issa’s case, The Lovebirds eventually landed on Netflix (it starts streaming May 22), and she still has one thing that wasn’t canceled: the fourth season of Insecure, out now on HBO—which, it turns out, a *lot* of people see as a lifeline. “Someone asked me if I felt pressure about this season coming on, and up until now, I hadn’t,” she says. “This fucking virus changed everything. Most of my mentions have been like, ‘Drop it, girl, stop playing, drop all the episodes at once’—like I’m HBO. And I’m like, What the fuck? We’re literally still mixing and editing.”
So, yeah, it feels like a lot. And it’s probably gonna feel like a lot for a while. But Issa will be fine, because most of us will, in some way, be lucky enough to be fine. At least, that’s what Issa’s boss-level confidence makes me believe, and fuck is it a relief. “We’re being forced to stop and just reevaluate, be creative in our approach,” she says. “Humans are resilient. We’re going to figure this shit out.”
If anyone can, it’s Issa. Just look at the before-before. Before she became a New York Times best seller or a Golden Globe nominee or the black social-media success story that turned her guerrilla YouTube series, The Misadventures of Awkward Black Girl, into an empire.
The story goes like this: Awkward Black Girl went viral in 2011—and then, nothing. Fast-forward to 2015: still waiting for Hollywood to catch up. Issa had already been developing Insecure for two years, with no idea that it would ever be picked up or go on to practically redefine TV. “That time was so frustrating because I had been working on the show for years,” she says, “and it just felt like the constant pressure of ‘your time is up, your time is now—so when’s it going to pop?’”
She also did other things. Like, a lot of other things. She wrote that book (also titled The Misadventures of Awkward Black Girl). She spent all her money (“my business manager was like, ‘What did you do?!’”) on a venture called ColorCreative that produced the low-budget pilots of writers she believed in. She launched Tea & Breakfast, a short-lived website intended as a black millennial response to sites like BuzzFeed and Thought Catalog. And she applied the same urgent mindset—if not us, then who?—to all of it.
(Before we keep it moving, a little sidebar: I wouldn’t be writing this right now if it weren’t for Issa. Back in 2014, my 9-to-5 was basically just furiously tweeting jokes on Twitter, hoping someone, anyone, would notice. Issa noticed and hired me to join Tea & Breakfast alongside other young black writers like Antwaun Sargent, Diamond Sharp, and Liza Dye. I was rewarded by Issa for using my own voice, not what I thought could get me hired. Now, I’m a TV writer too.)
Issa, of course, brushes off her role in these origin stories. Collecting people who experience the world as she does—and giving them opportunities—is just what she does. She wants to know “who’s hungry” and surround herself with other black creatives so she “can just work. We don’t have to break things down. We understand each other. For me, it’s just about finding who’s got it, who’s got something to say, and who just feels down and with it.”
Not that any of it is easy. Issa is all too aware that there’s an extra spotlight on black shows, which carry the weight of needing to be all things to everyone. And as an artist whose mere presence means so much to black audiences, particularly young black women yearning to see themselves represented onscreen, Issa’s under more pressure than white actors who aren’t viewed through a monolith lens. “If she does half a thing wrong, she’s under scrutiny because she’s held up to be the perfect black woman for young people,” says Robin Thede, the creator of A Black Lady Sketch Show, which Issa (of course) produces. “I always admire how she takes that in stride.”
Well, maybe not always in stride. “Candidly, it’s terrifying,” says Issa, as we talk about buzzy, big projects like The Photograph, the romantic drama she also starred in (but *gasp* didn’t write or produce) this year. “The bigger you are and the more people know your name, the more people you’re stumbling in front of.”
Honestly, it’s all still sinking in, even this interview. “It almost just feels like I fooled people. Ha, ha, you put me on a magazine cover.” Also, in an industry that wasn’t built for black creatives to have long-term success, she worries how long her “window” will last. “The blessing is like, Okay, I can for sure make my own opportunities, and that’s fun,” she explains. “But I also want to be able to…I want to deserve to be here, and that’s part of what keeps me up at night.”
She’s not just talking about putting out work that, in the right-now, is such a needed break from reality that people are literally begging her for it. She’s not talking about the ratings, the reviews, or the awards.
She’s talking about legacy. “I want to be a pop culture staple—a black pop culture staple,” she says. “I want to have an impact on my community. Everything I’ve done has been for—and in thinking of—black people, and I don’t take this moment lightly. I want to do right by us, at the end of the day.”
She’s still not sure what exactly that kind of success would entail. Or if she’s even the person everyone else wants to be doing right by them (she is). “It’s presumptuous because, like, nobody’s counting on me,” Issa says, finishing her thought with a laugh. “Nobody’s like, ‘She got to do it!’” (We are.)
Fashion by Cassie Anderson. Cinematography by Janet Upadhye. Video production by Meghan Allen. Video editing by Desi Sulca. Hair by Nicole Newland. Makeup by Joanna Simkin for The Wall Group. Manicure by Thuy Nguyen for SWA. Props styled by Andy Henbest for Art Department. Production by Crawford & Co Productions.
On Issa: Hexagon look: Gucci dress, earrings, and ring; Monies bracelet. Lawn chair look: Ulla Johnson dress; Pierre Hardy heels; Gucci sunglasses; Monies earrings and ring (right hand); Ariana Boussard-Reifel bracelet; Dinosaur Designs ring (left hand). Blue background look: Valentino dress, earrings, and belt; Giuseppe Zanotti heels; Iris Apfel x Bernardaud ring. Rubik’s Cube look: Jonathan Simkhai dress; Marni earrings; Oscar de la Renta necklace. Black and white look: Caroline Constas dress; Kenneth Jay Lane earrings; Auvere ring.
