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.”
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?”
At the time of the interview, the series finale has yet to be written, and Rae wants to make sure they’re following through on her original vision. Recently, she sent a “long, passionate letter” to Penny and executive producer and writer Amy Aniobi that began, “Okay! Came up with an idea I’m really excited about that consolidates some of the ideas that have been brewing for us…I was thinking of my own life and some of my long-term and long-distance friendships—and thinking of the reasons to gather our girls, that feel central to our show.…”
Rae says the last three episodes of the series should feel like a cohesive triptych, and the fact that the episodes are being filmed out of order this year makes it even harder for her to track the season’s arcs as she watches incoming cuts. “I don’t know if it’s because it’s not complete, but I’m like, Is this”—she comically grits her teeth and lowers her voice—“not good?”
I take all this to be a healthy, or at least semihealthy, sign of creative ambition. But when I ask Rae if she’ll star in her own shows in the future, she says something that surprises me, and I realize there’s another reason she’s putting pressure on herself. “Girl, no! I’m never doing this again,” she says. “Before you asked that question, I told myself I would never write and be in a show that I created again. It takes up a lot of your life, and I like to do a lot of things.” Rae slows her cadence, choosing her words carefully. “I love doing this show. I’m so grateful to be able to do this show. But that’s just not really for me.”
The next time Rae and I talk, she’s wearing a giant pink Farm Rio cardigan over a white tank top and super-fleece sweatpants. She’s just received her first COVID vaccination, which she got at the Crenshaw Mall with a group of friends. “That shit has wiped me out,” she says. “I’m talking about chills, body aches. It’s not great. But yay, it means my immune system is good.”
Even sick, she woke up at 4 a.m.—as she does every morning—to go for a walk and attend to business in the quiet hours. Rae also clears her mind by writing in her journal at least three times a week. She tried therapy in the past but is holding off until she can safely meet someone in person after the pandemic. “I guess work has been my outlet, which is sad,” she says. “Sometimes I’m like, Oh, I don’t have anybody to talk to who understands. [But] I also never want to be in a position to offer up my problems to somebody.”
After her journal, the closest thing Rae has to therapy is astrology, though she insists that she’s not hyper woo-woo about it. She’s astrological in the sense that she checks out the app The Pattern for her horoscope from time to time and is fully aware of her Capricorn traits. Also, when I inform her that I’m a Scorpio, she has a question locked and loaded: “Do people tell you that you’re crazy?” (Answer: not to my face.)
I ask Rae to read me her daily horoscope. She pushes her rolling chair away from her desk to grab her phone across the room—this shocks me a little, frankly, because everyone I know needs to maintain skin-to-skin contact with their phones at all times—and opens the app. After a moment, she laughs to herself, and a hint of embarrassment creeps up her throat. “Well, now it’s going to seem arrogant,” she says. “It just says: ‘Natural networker. You know how to put others at ease. In social situations, you’re intuitively aware of what people are thinking and do what’s appropriate in response.’ ”
Well, it’s true, I tell her. I’m at ease in this social situation. Rae lets loose with a big laugh.
Anyway, it’s not a bad reading for someone who built her career out of being comically uncomfortable in her own skin, literally stamping her brand with the words awkward and insecure. She attributes all this partly to her family. “We all think about the same uncomfortable situations and have very similar observations,” she says. “You could replace me with any of my siblings in Awkward Black Girl, and you would still get the same humor.”
Rae comes from a big, extremely close family. Asked who the biggest Insecure fan in the bunch is, she’s hard-pressed to choose: “Maybe my sister. I don’t really know. Maybe my oldest brother on the low.” Rae was born in Los Angeles to an African American teacher, Delyna, and a Senegalese pediatrician, Abdoulaye Diop. She has four siblings: Lamine, Amadou, Malick, and Elize. (One of Rae’s first web series, a mockumentary called Fly Guys Present “The ‘F’ Word,” was inspired by Lamine’s rap group and starred Lamine himself.) The family moved around during Rae’s childhood, staying for a time in a luxurious home in Dakar, Senegal. In her 2015 memoir, Rae wrote that they had a multilevel house, a security guard, and two maids: “Life was great, for two years. Until my father attempted to build a hospital in Senegal and instead got ripped off by the government, losing most of his money in the process. That’s when, to my sadness and my older brothers’ relief, we packed our bags to return to the States.”
The Diops moved to Potomac, Maryland, then back to L.A., where Rae’s father was locally known thanks to the Inglewood clinic on Manchester Boulevard that bore his name. Her parents divorced when she was in high school. That strained her relationship with her father for several years, though she talks warmly about him now.
Rae, who speaks Wolof and French, hasn’t been back to Senegal since 2009. It’s one of the few topics that makes her noticeably gloomy. “I feel disconnected from it,” she says. “I wanted to go back in 2020. That was going to be the year, and then that got derailed. But so much has changed.” She pauses, falling silent for a few seconds. Much of her extended family has since left Senegal. “Yeah,” she finally says, loading the word to the hilt. “I just know that it wouldn’t be the same.” She’s proud of her Senegalese side, though, and eventually hopefulness warms up her voice. “I would love to have a house there,” she says. “I would love to take my future kids there, and maybe give them the same type of childhood and appreciation that my parents gave us.” Rae’s fiancé, businessman Louis Diame, is Senegalese and Vietnamese. The pair met while Rae was in college, and she said in her memoir that “from the very first five-hour conversation,” she knew she had met her match.
In 2011, Rae made her web series, The Misadventures of Awkward Black Girl, and carved a lane for herself, as well as for other Black girls who were gawky and antisocial, in the key of Tina Fey in 30 Rock, or Larry David in everything. (Both are frequent touch points for Rae.) The archetype existed before she gave face to it, not that the industry’s largely white bosses recognized it. Both in interviews and in her memoir, Rae has told the story of a TV executive who suggested that Lauren London, an actor who got her start playing the love interest in a spate of music videos and in films like the drama ATL, would be a great fit for a cable version of Awkward Black Girl. The moral of the story was not only that executives were out of touch with Black women, swapping one for another even when they were nothing alike, but also that dark-skinned Black women could be edited out of their own narratives. In a twist that Rae didn’t anticipate, the anecdote hurt London’s feelings. “One of my biggest regrets, naming her,” she says. “She took offense to that.”
The duo made peace at Diddy’s birthday party two years ago, Rae says, spurred by London’s partner, the late Nipsey Hussle. The rapper approached Rae at the party and encouraged her to make things right. “He was like, ‘You should just talk to her. Let me set it up,’ ” she says. “It actually sparked an amazing two-hour conversation. We had so much in common. She was like, ‘People don’t understand, I’m an awkward Black girl.’ In the same way that I was upset about the limited portrayal of Black women, she was like, ‘People do the same thing to me.’ I completely get that.” The conversation burrowed itself in Rae’s brain. With Insecure, she has actively expanded the scope of characters that Black women can relate to—and that mission will continue to guide her.
Rae is now producing such a variety of things that she’s like someone who just came back from a buffet with a towering plate. Next up is Sweet Life, a docuseries in the vein of Laguna Beach and The Hills about Black 20-somethings living in L.A.’s tony Baldwin Hills neighborhood. The show was inspired by the 2007 BET series Baldwin Hills, which Rae loved. (One of the managers at ColorCreative, Rae’s initiative promoting inclusion in TV, was a former cast member of the series.) Alongside Adam McKay, Rae is also producing an adaptation of Nice White Parents, a quietly infuriating podcast about a public school in Brooklyn. She’s writing, producing, and starring in Perfect Strangers, based on the Italian dramedy Perfutti sconosciuti, about a group of friends learning each other’s darkest secrets during a chaotic dinner party. And then there’s the second season of A Black Lady Sketch Show, the Emmy-nominated series that Rae executive produces.
Vanity Fair can exclusively report that Rae is also working on a revival of Matt Damon and Ben Affleck’s HBO docuseries Project Greenlight, which gave money and support to aspiring filmmakers. The series is known less for the films it produced than for a scene in its final season, in which Damon pushed back against producer Effie Brown for saying that the casting for the participants in the series should have been more inclusive. “When we’re talking about diversity, you do it in the casting of the film, not in the casting of the show,” he insisted. “Wow,” Brown responded, visibly stunned. The scene sparked a backlash and prompted Damon to issue a public apology. (Project Greenlight was canceled in 2016.) Rae’s excitement lies predominantly in offering overlooked directors a place to shine: “I want this version of the show to make filmmaking feel attainable.”
Those who love Rae’s onscreen presence will be relieved to hear that she’s also lining up more film and TV roles. She’s eager to polish her acting chops, inspired by collaborators like LaKeith Stanfield, who starred with her in 2020’s The Photograph. Rae remembers Stanfield telling her that he was still shaking off a character he’d recently played in another film. “He was like, ‘You know how you’ll just black out when you’re playing a role?’ And I was like, ‘Uh…yeah, yeah, yeah.’ ” She was only pretending she could relate, she tells me now: “I’ve never had that opportunity. I just want to be able to see what I can do.”
Years ago, Twitter became obsessed with a photo of Rihanna and Lupita Nyong’o sitting side by side at a Miu Miu fashion show, the former in espionage-grade shades and a furry yellow and black coat, the latter in a crisp collared shirt and thick glasses. Users called for Ava DuVernay to direct a film based on the shot, with a script by Rae. In 2017, Netflix went ahead and actually secured a deal for the concept, though Rae artfully dodged any confirmation of the news when I interviewed her later that year. She did, however, concede that the four of them had connected and were on a text chain together. Four years later, it seems less and less likely that the movie will ever be made, though Rae still gets questions about it. “Every year without fail,” she says when I bring it up again. “Zero comment! Nothing has changed.”
As if to taunt me some more, Rae tells me there is some kind of secret movie with someone in the works, but she can’t talk about it in case it doesn’t materialize. “Otherwise I’ll just be really sad, like, ‘Damn, I guess it’s not happening—and I talked about that shit.’ ”
“And I’ll blame you,” she adds. “I will.” She raises her brow and keeps a straight face. Then she busts out laughing.
I sit in on one more conference with the Insecure team before my time with Rae is over. It’s known as the “tone” meeting, and it’s less about logistics and more about the feeling of an episode, and whether it’s hitting the proper emotional beats. It follows directly after the production meeting, the number of participants dwindling from 73 to 18. Rae can be more animated here. More honest.
The group discusses the various tension points that occur in the episode, including how ugly an argument between two characters should be. (Aniobi, the writer and producer, says that she thinks it should have “the energy of ‘fuck you,’ but saying ‘fuck you’ is too far.”) They discuss the deep fan hatred for Lawrence’s ex, Condola, and whether they can give her a redemptive scene that won’t feel like they’re simply pandering to their audience. They discuss one character going on a series of dates and how he should start with a girl who doesn’t feel too far out of his league.
“A layup,” Penny says. Rae gives him a disapproving look, but he continues: “Don’t women go on dates for food? ‘I’m about to take this n-gga to get me a meal.’ Don’t women do that?”
“I’ve never done that in my life,” Rae retorts, sounding very much like she has done that in her life.
The room devolves into sidebar nation, everyone debating Penny’s point.
“I don’t know,” Rae says finally, trying to end the tangent.
“That was the most grandma answer!” says Penny, mimicking her with a creaky voice. “I don’t know.”
The meeting gets reflective at times, which is to be expected when a show is winding down long-running plots. The group talks about tertiary characters in an upcoming episode and how they don’t want to repeat mistakes from a past season, in which two side characters felt too much like caricatures for Rae’s liking.
“What were we doing?” Rae says, with a resigned laugh. “That wasn’t our greatest moment.”
Everyone agrees, until writer-producer Laura Kittrell interrupts. “We did great,” she says confidently, which causes everyone to dissolve into laughter. “It’s the last season. Let’s celebrate ourselves. What are we doing?”
“I’m sorry, you’re right,” Rae says. She shakes her head, and smiles broadly. “Progression! Growth!”
Hearing all this, I remember Yvonne Orji telling me about a conversation she had last fall with her costar Jay Ellis. “I was like, ‘Hey, fam—what do we do after this?’ You know when you work with people you like and you genuinely enjoy it? And there’s no beef and you’re doing good work? I imagine it was like that after the Obamas left the White House. If you were a staffer, do you just retire? Because, like, who you gon’ work for better than Barack and Michelle? Like, who? Does this exist anywhere else? We had such a beautiful moment that probably can’t be replicated.”
Fortunately for them and us, the show’s not over yet. During the tone meeting, Jonathan Berry, who’s an executive producer, asks what Rae and Kittrell were laughing about in the production meeting, since it was obvious that they were messaging each other constantly.
“It’s gotta be about me, right?” he says.
“I’m sitting here going, Maybe it’s about me!” adds Aniobi.
Rae shakes her head fondly. “Wow,” she says. “Insecure much?”
HAIR, FELICIA LEATHERWOOD; MAKEUP, JOANNA SIMKIN; MANICURE, ERI ISHIZU; TAILOR, HASMIK KOURINIAN; PRODUCED ON LOCATION BY LOLA PRODUCTION; FOR DETAILS, GO TO VF.COM/CREDITS.
More Great Stories From Vanity Fair
— A First Look at Leonardo DiCaprio in Killers of the Flower Moon
— 15 Summer Movies Worth Returning to Theaters For
— Why Evan Peters Needed a Hug After His Big Mare of Easttown Scene
— Shadow and Bone Creators Break Down Those Big Book Changes
— The Particular Bravery of Elliot Page’s Oprah Interview
— Inside the Collapse of the Golden Globes
— Watch Justin Theroux Break Down His Career
— For the Love of Real Housewives: An Obsession That Never Quits
— From the Archive: The Sky’s the Limit for Leonardo DiCaprio
— Not a subscriber? Join Vanity Fair to receive full access to VF.com and the complete online archive now.
Learn More: entertainment near me,entertainment synonym,entertainment center ideas,entertainment lawyer,3 arts entertainment,entertainment law,entertainment 720,entertainment work permit,entertainment room,entertainment logo,entertainment trivia,entertainment wall units,entertainment wall,entertainment industry jobs,entertainment in the 1920s,entertainment and sports arena,entertainment attorney,entertainment media,entertainment design,entertainment marketing,entertainment lawyer salary,entertainment benefits group,entertainment jobs los angeles,entertainment jobs atlanta,entertainment venues,entertainment brands,3 piece entertainment center,entertainment and sports arena dc,entertainment places,entertainment jobs nyc,entertainment hobby shop jungle,entertainment videos,entertainment reddit,entertainment 1920s,yg entertainment actors,p nation entertainment,entertainment voice,entertainment venues near me