What Issa Rae Wants: She’s Saying Goodbye to Insecure, Rebooting Project Greenlight, and More


    What Issa Rae Wants: She’s Saying Goodbye to Insecure, Rebooting Project Greenlight, and More

    Issa Rae doesn’t make vision boards anymore, but let’s take a look at her last one and see how she did. She assembled it from magazine photos, headlines, and other odds and ends at the behest of her publicist back in 2013, when she was between projects. It’s now framed on a wall in her makeshift home office in Los Angeles. Among other things, Rae, who was born Jo-Issa Rae Diop, wanted to cook healthier meals. To fall in love. To have a house with a pool. The board, I can’t help but notice when she Zooms me around the room, also has an HBO logo on it and the words “TV Writer.” You could say the thing worked. Rae has indeed fallen in love—she has an enormous diamond engagement ring, about which she deadpans, “I’m fully single.” And as for her TV career, the world has increasingly fallen in love with her.

    When it debuted on HBO in 2016, Rae’s show, Insecure, was the first comedy in the network’s history of more than four decades to be created by and star a Black woman. It was an instant hit, praised by critics for its energizing humor, its complex depiction of dating, and its adoring view of Los Angeles. Insecure is to Inglewood and Crenshaw what Sex and the City was to Manhattan. The show hinges on Rae, not just as an executive—she cocreated it with Larry Wilmore and still writes and produces—but also as a nuanced, deeply relatable comic actor. As Issa Dee, she is an everywoman with a Hollywood sheen, a glowed-up, doe-eyed version of you and your friends.

    Rae recently signed an overall production deal with HBO’s parent company, WarnerMedia, said to be worth $40 million. She now has so many ventures in the works that she bought a building seven minutes from her home to serve as her headquarters. With Insecure set to end after its fifth season this year, Rae’s future is a little more open, a little less defined by the demands of a TV production. She’s 36 and has nailed a lifetime’s worth of vision-board visions in less than a decade. I’ve witnessed this ascent, having interviewed Rae several times in her career: in 2016, before Insecure began; later that year after Rae was nominated for a Golden Globe; in 2017 after she was snubbed for an Emmy; and last year in the midst of the pandemic. Her personality, somewhat remarkably, is the same as it ever was: funny, friendly, and quick, with a dollop of Eeyore-esque self-deprecation. I compliment her for achieving so much. She insists she hasn’t done anything at all. “I have one web series, one show,” she says. “I haven’t even written a movie. Of the shit that’s mine, I don’t have much.”

    Clothing and a belt by Saint Laurent by Anthony Vaccarello; earrings by Tiffany & Co. Elsa Peretti. Photograph by Adrienne Raquel.

    When I talk to Rae this time around, she and her team are in the throes of shooting the final season of Insecure, and she’s determined not to squander the goodwill and devotion of the audience, which grew exponentially during quarantine last year. “I’m finding myself putting season-one pressure back on the show again,” she tells me. She’s even been rewatching Insecure from the beginning, which has been a complicated experience. “All these memories come up, so I can’t watch it purely objectively. And then, of course, you look at performance stuff, you look at hair stuff, you look at appearance stuff. You’re just like, Okay, wow, I went on TV like that?”

    Details are everything on Insecure. Originally, the show seemed like a glossier version of The Misadventures of Awkward Black Girl, the gleefully misanthropic web series that helped Rae get Hollywood’s attention. Insecure follows Issa Dee, an aimless 29-year-old, and her best friend Molly, a polished lawyer. Issa, the character, is goofy and endearing. She’s working a dead-end job at a dubious nonprofit called We Got Y’all—the company’s logo is a white hand holding the silhouettes of three Black children—and is initially stuck in a relationship with a jobless couch fixture named Lawrence (Jay Ellis). The first season was funny and sexy but grounded: Issa kicks back in her room, hangs out with her friends, and blows off steam by performing nerdy raps and aggressive duologues to her own reflection, a character lovingly dubbed Mirror Bitch.

    As the show grew, HBO became increasingly excited, upping budgets and scheduling it after Game of Thrones and Ballers, which yielded a huge ratings boost and a spot in the network’s lineup of must-see TV. Ending the show after five seasons was always Rae’s intention. “I pretty much go with my gut, and this is what my gut’s been telling me forever,” she says between sips of Jack Daniel’s honey whiskey with bitters. COVID has, naturally, made production harder. Extras for crowd scenes have to be quarantined together in a hotel. Episodes have to be shot out of order, and work hours have to be trimmed. Production also had to be shut down for two weeks after a background actor tested positive. Rae happened to be the person closest to them and had to quarantine.

    On a Wednesday morning in March, Rae invites me to sit in on a virtual production meeting with her and 72 crew members, during which they inch through the logistics of shooting the third episode of season five. First assistant director Toby Burge reads through the script, pausing for notes and brainstorms. In the episode, Issa’s once and possibly future boyfriend, Lawrence, has to cook a meal. It will probably last all of four seconds onscreen. Still, it sparks a debate: What should Lawrence be cooking? What will it connote about his skill level? What will it say about his status in life, since he’s transformed over the seasons into a hyper-successful tech bro? “Lasagna!” Rae says. Someone else suggests ramen. Showrunner Prentice Penny jokingly pitches lobster thermidor. And so on. Ultimately, director Ava Berkofsky—who wears huge glasses like Sophia from The Golden Girls and radiates a tranquil energy—renders her verdict. “Lasagna’s complicated,” she says. “That’ll look good.”

    During the meeting, Rae is by turns attentive and dreamy, surreptitiously texting her coworkers, then trying to hide her smile when their responses make her laugh. She interrupts only occasionally, like when it’s suggested that Lawrence pay for dinner at a restaurant by pulling out his money clip. “He has a money clip?” Rae says. “Have we established that before? That’s what men do? What is he, a pimp? Y’all have money clips?” Penny unmutes to back her up: “He should not have a money clip. Just a wallet. He should just have a wallet.” They move on to the next scene.

    Rae seems like a surprisingly hands-off leader—not a micromanager but a team player on a team she built and trusts. Yvonne Orji, who plays Issa’s bougie best friend, confirms this for me, noting that Rae took a chance on Penny, Melina Matsoukas, Orji herself, and many others. “We were all first-timers in so many different ways,” she says. “I was a comedian, but this was my first major acting job. Prentice had been a writer, but this was his first showrunning gig. Melina had been doing music videos, but this was her first TV directing gig. Issa had to believe that we could do it, and she trusted her baby with us.… I wish that more people in power could have the same attitude. She literally puts people in positions and allows them to do their jobs. She lets people grow.”

    During one of our Zoom interviews, Rae gets a text from costar Natasha Rothwell, who’s directing an episode even as we speak. “Yvonne says she’s killing it,” Rae says proudly.

    But, lest I believe all the stuff about her being a beloved, beneficent leader, Rae assures me that she’s actually been driving her writers up the wall lately, particularly with her Insecure rewatch: “We’d be working on story and I’d be like, ‘But I watched season three, episode two last night.…’ And they’re like, Ugh, what’s she got to say now? What are you about to change now? What are you about to bring up?”

    Published at Tue, 18 May 2021 12:00:00 +0000