“Awkward Black Girl” Goes to Hollywood

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Photo: Benedict Evans

Everything about Issa Rae’s arrival to lunch in Tribeca on a sunny September afternoon announces she’s about to be a huge deal. There’s the black SUV that’s just ferried her from an interview with Oprah’s BFF, Gayle King; an entourage consisting of Rae’s personal publicist and the rep for her new HBO show, Insecure; the gorgeous, fitted burgundy dress with a bejeweled collar that she’s wearing because her stylist handed it to her. “Girl, this is all a deception,” she says when I ask if she always looks this glam. “T-shirts, jeans, and Chucks are my life.”

Rae, 31, is instantly warm, not to mention a great hugger. She’s what one might term “obliviously focused”: She completely misses the young black woman working the cash register at our lunch spot who’s jumping up and down, grabbing her co-worker, saying “That was Issa Rae!” loud enough to be overheard. But then she comes in razor-sharp with a quip when you couldn’t even tell she was listening.

It’s right on brand, actually. You may only know Rae from the many Insecure posters plastered across subway stations, bus stops, and billboards near you, but internet cognoscenti of color have been following her for years via her popular YouTube series, The Misadventures of Awkward Black Girl, which debuted in 2011, and her New York Times best-selling memoir of the same name. Our first 15 minutes together are, fittingly, awkward — mainly because Rae is starving and, at her publicist’s behest, we hop around to three different lunch spots before settling on one. A clear introvert, Rae stays quiet and goes where she’s told but lights up whenever there’s a subject she can nerd out about, like breakfast (“Chia pudding is bomb!”).

Awkward Black Girl, Insecure, and her memoir may all be shades of Rae’s life — or the kind of life she might have had if she weren’t driven enough to create a web series and TV show and write a book by 30 — but they’re also, in sum, a mission statement: to depict black women as imperfect subjects, worthy of fascination, with precise, observational humor. Or, more specifically, to depict the black women she knows, including some version of herself, as full-bodied human beings, ones who might sleep with an annoying co-worker while drunk at an office party and then crouch out of view every time they see him, which is the premise of the first episode of ABG. In the web series, Rae played “J,” a bored, introverted, early-20s office worker, dealing with abundant humiliations at both work and home, who would often make up hard-core raps about her frustrations. It was unlike anything on network TV: a show where a black woman character didn’t have to be a strong, high-powered anything or a bitch-slapping mess to be compelling.  

When the HBO series was announced in 2013, the internet was quick to label her “the black Lena Dunham,” a comparison Rae hopes is in her past. “I don’t like that,” she says. “That’s the dumbest and laziest thing to do. It’s insulting to me and to her, especially to her. We’re not telling the same stories. Yeah, we’re both young women on HBO, but... I wish I could think of men on HBO — they don’t do that shit with them.”

For one, the major, ongoing criticism of Dunham’s show is that there are no substantive roles for people of color, where Rae’s whole perspective is centered on them. Rae counts among her mentors Debbie Allen, Girlfriends creator Mara Brock Akil, Love & Basketball director Gina Prince-Bythewood, and Selma director Ava DuVernay, who was such an early fan she contributed to a Kickstarter campaign to fund ABG’s second season. “That was back when no one except a really small group of black people online knew what she was doing,” DuVernay tells me. “So often in the images of black women, we have to embrace a sense of our intelligence or our glamour — all of which is true — but we also are awkward and nerdy.” When I tell DuVernay that Rae considers her a mentor, she says, “I see her as a peer more, actually,” before whipping out her phone like a proud sister to show me a video she took of an Insecure banner she saw on a bus. “I’m such a nerd, I keep taking pictures whenever I see the signs,” she laughs. “They’re all over L.A.!”

Rae’s sudden ubiquity is particularly gratifying for her fans, considering she hasn’t been seen onscreen in a major role since the last ABG video was posted on YouTube in February 2013. News of her HBO deal broke that summer, and then, with the exception of her memoir, she disappeared from public view. HBO’s production process is notoriously, deliberately slow, an experience Rae called “frustrating.” But if those Insecure posters aren’t enough of a clue, the network seems to be betting big on Rae’s half-hour comedy, the first show in HBO history to be co-created by and starring a black woman.

Insecure is the story of two black girlfriends stumbling their way toward 30 in South Los Angeles. Rae plays a character also named Issa, a listless, “aggressively passive” 29-year-old working at an educational nonprofit, We Got Y’All, run by culturally insensitive white people helping inner-city kids of color (basically, the worst possible job Rae could imagine: The logo is a big white hand cradling little black children). She’s also half in, half out of a relationship with her unemployed boyfriend of five years, Lawrence (Jay Ellis). Newcomer Yvonne Orji shares almost equal screen time with Rae as her best friend, Molly, a successful lawyer who can’t believe she’s still navigating the horrifying waters of “bottom of the barrel dudes” on online-dating sites. Reviews of the series have been enthusiastic. Variety called it “a symphony of one character’s attempts to avoid her own problems for as long as possible,” while New York’s Matt Zoller Seitz writes that “few series have conveyed such a clear sense of all the different people that black professional women are required to be, and none has done such a fine job of conveying this visually as well as in performance and dialogue.”

HBO isn’t just betting big on her show — it’s betting big on Rae, who’s eager to be in a position to empower other black creators, so maybe next time it won’t take so long for someone like herself to get a show made. The network has given her a two-year first-look production deal to develop the projects of other writers of color. After an afternoon with her, it’s easy to see why: She’s provocative and knows how to land a point, and, more important, she can keep your attention while she makes it. When I mention I thought Nick Cannon’s moves in King of the Dancehall were pretty good, within seconds, she’s deftly maneuvered us into a discussion of Channing Tatum’s dancing skills: “Did you think Channing Tatum could dance in Step Up?” I’ve never seen Step Up. Rae presses on: “Did you think he could dance in Magic Mike?” I can’t remember. “If you had to compare Channing Tatum dancing shirtless to Nick Cannon dancing shirtless …” This seems like a loaded question, I tell her. “It is!” she says. “I’m very, very irritated that he made his career off being basically a hot white guy who can dance … and he can’t dance!” She should know: Rae wrote an entire chapter in her book called “When You Can’t Dance.” “On a scale of Michael Jackson to Drunk White Girl,” she writes, “I come in at Drunk Black Girl.”

Not knowing her place or where she’s going has been the major theme of Rae’s life. Her book is a chronicle of not fitting in with white peers or being black enough for black peers — from Potomac, Maryland, to Dakar, Senegal, where she spent parts of her childhood, and finally where she considers home, Inglewood, California. There are some pretty frank discussions of her Senegalese father’s infidelities and her own history of cheating on early boyfriends. It also includes helpful tips on how to react to people’s comments about your nappy hair and a field guide to the many types of black people (the Ambitious Black, the Militant Black, the Not-Black Black), and how the Awkward Black should approach them: “Don’t make jokes. This black is serious. Play along or back away.”

If the Awkward Black Girl web series is the dramatization of those feelings, Insecure is their maturation. “I wanted to create a more tonally real show that felt grounded,” says Rae. Since she had no conventional TV experience before she began workshopping the HBO show in 2013, her management company set her up with Larry Wilmore, then a correspondent for Comedy Central’s The Daily Show, who had created series like The Bernie Mac Show and Eddie Murphy’s animated The PJs. Wilmore watched Rae’s work and was impressed. “Her point of view was very clear and concise,” he says. “She has this writer’s voice, and that was the first thing that came across. The second was herself. I call her the Quiet Storm: She seems quiet on the surface, but there’s a lot going on underneath.” Wilmore was brought in to be something of a supervisor, but as soon as he met Rae, he realized he wanted to be in the room where it happens. “We got along instantly, making each other laugh, and I mentioned to her, ‘Look, I would rather just create this with you and figure out the show with you and co-write it.’ She’s like, ‘Are you kidding me? That’s awesome!’”

Every day for months, they would meet at Wilmore’s apartment in downtown Los Angeles for lunch, and he’d interview Rae about herself: her background, her sex life, her doubts. Out of those conversations, they landed on a theme for a show about a smart, educated woman who has everything going for her but isn’t sure how to get there. (The original title was actually Non-Prophet, because Issa the character worked at a nonprofit but she couldn’t predict her future.)

Rae and Wilmore were thrilled with the pilot they turned in, and then … crickets. HBO doesn’t put shows on the air until they’re absolutely ready, and in Rae’s case, it took from her meeting with Wilmore in the summer of 2013 until now. In that time, Wilmore produced early episodes of ABC’s Black-ish, which he left to host Comedy Central’s The Nightly Show. “And now it’s canceled, and now Insecure comes out!” he says, laughing. “I’ve had this whole career happen in the time between when we wrote it and now.” (Wilmore eventually had to step back from being showrunner on Insecure to do the The Nightly Show. He was replaced by former Brooklyn Nine-Nine producer Prentice Penny.)

“I was 100 percent frustrated with the process and the pace, because I was coming from the internet, where I could have something produced, put it up, and get immediate reaction,” says Rae. “So I was like, ‘What is taking so long?’ They have a history of treating things like movies in terms of development, and I was just not about that life.”

The biggest note in the final pilot was taking the focus off just the Issa character and centering it on the friendship between these two particular black women — HBO loved the Molly character and wanted more of her. Rae liked the idea, too. Positive, supportive black female friendship is something she strongly believes hasn’t been shown on TV since Girlfriends went off the air in 2008. In its absence, the majority of representations of black women are on reality shows like the Real Housewives franchise, VH1’s Love & Hip-Hop, and Flavor of Love — the show Rae says was “my tipping point for, I can’t do this anymore. It was black women backstabbing each other to compete for an ugly black dude. It’s the most popular show on TV because we’re starved to see ourselves, and it’s a shit show.”

In particular, she wanted to show the kinship of the black women she knows: the way her friends roast each other, affectionately call each other “bitch,” and then make up over Cheetos and Frito-Lays dip. In a television landscape that includes Scandal, How to Get Away With Murder, Being Mary Jane, Atlanta, Pitch, and DuVernay’s Queen Sugar, the timing couldn’t be better for a black-led series with such a specific vision — it takes a bit of the pressure off. “I’m not the singular voice of black women, and I feel like more is coming,” she says. “If this was the only show featuring a black woman at the time, I’d feel the onus would be on us to represent every black woman and every black female friendship, but I don’t see that.”

Still, there’s no doubt that Rae is breaking ground, particularly by having two black female leads, not to mention a mostly black supporting cast. “In traditional Hollywood, [Issa and Molly] would normally be treated the same: They’re The Black Girl,” says Wilmore. “They would be up for the same part because there would be only one part of ‘the friend,’ and she would be in support of the white person, who we were really supposed to be interested in.”

In creating the Issa character, Rae mined her own dating experience. (She’s currently in a relationship, and her experience online dating predates Tinder; she actually asked me if you swipe left or right if you like someone.) “I wanted to show how scary it is,” she says, “to be with someone for so long and not be sure.” She saw her 20s as a chance “to ho out.” “It was the first time I felt attractive, like I had interesting guys that I fell in love with,” Rae explains. “But then: Do I really want to be with you? And what does that mean to stay with someone for so long, and what does it mean to leave them?” Through her character, she also wanted to imagine how scary it would be to be alone and have to face yourself.

Molly’s single status gave her the chance to explore what her friends — and the single women in her writers’ room — are experiencing on dating apps. “I wanted to put out there what it’s like to date as a black woman and feel like you’re not that desired. We’re getting swiped left the shit out of, and that’ll be taking its toll,” she says. “There’s a feeling of, Why not me? What’s wrong with me? I’m successful, I’m driven, I think I’m a catch, so why doesn’t anyone want me?” But by showing that Molly has ridiculously high standards, Rae also makes the answer more complicated than “All men suck. “ “A lot of men do suck!” she says. “But at the same time I wanted to ask, ‘What is it about you?’ I didn’t want to have this thing like, ‘Oh, poor black women victims.’ What can you look at within yourself that might be the problem too?”

Setting Insecure in Inglewood, the historically black neighborhood where Rae grew up and currently lives, was deeply important to her. She wanted to represent an L.A. that’s rarely shown on screen, except for, “like, a gang movie or ‘Oh, shit, we’re going to the hood!’” she mimics. “Whenever I see L.A. in movies and TV, it’s Beverly Hills, Hollywood, or hipster Silver Lake. We get to represent an area that’s not only diverse in terms of ethnic makeup but also socioeconomic, where people who are affluent and who are living in poverty mesh — that’s the culture of the area.”

That might not be as easy if the show gets a second season. The neighborhood is slowly beginning to change, and locations they shot in have since been bought by developers, “so our show ended up being a time capsule of sorts,” she says. In the pilot, a scene where Issa raps a song about Molly called “Broken Pussy” is shot at a club called Maverick’s Flats that Richard Pryor used to go to. “His coke room is in that lounge, and now it’s being sold for $3.75 million,” says Rae, wistfully. One of the Roscoe’s Chicken and Waffles they shot at is already gone. “They’re going to put hotels in there,” she says. “It’s a nightmare. There’s a Whole Foods coming. It’s over!” She admits: “I do love Whole Foods … I just want the benefits of gentrification without the gents.”

Rae may not be able to control the changing racial makeup of her neighborhood, but she has been working hard to change the racial makeup of Hollywood. When we meet, she’s lugging around a giant leather backpack like a security blanket, even though she has a whole SUV to store it for her, and it looks — to borrow a phrase Rae uses often — heavy as fuck. (Every Insecure episode title ends with the phrase: “Messy As Fuck,” “Thirsty As Fuck.”) “This is my shit, though!” she says, laughing, when I poke fun at her. It has her precious laptop full of scripts and ideas for how to conquer showbiz with other black women.

During those three years she spent in slow development on Insecure with HBO, “I basically spent all my money,” Rae says, launching an initiative called Color Creative to help other minorities and women by producing their web series and launching them on her YouTube channel. “I’ve been doing a lot of shit behind the scenes,” she continues, “trying to change what I thought sucked about the industry.” It’s work she’ll now be able to amplify through her first-look arrangement with HBO. “They gave me a deal that’s basically, ‘Be a producer and bring us shows and people you’re excited about, and we’ll make the show,’” Rae says. “It’s hella dope. That means I won’t have to scrounge for money for our YouTube series.” The deal is to develop one show a year for two years. She hasn’t picked anyone to work with yet, but says she’ll be able to launch TV shows “either on HBOGo, HBONow, and, if they like, it, HBO proper.”

The idea for Color Creative stemmed from the biggest disappointment of her career. After ABG, she spent a year writing a pilot with Shonda Rhimes and Betsy Beers for a show called I Hate L.A. Dudes, which would have been Shondaland Production’s first comedy, starring Rae as a 20-something fumbling through dating, only to see her voice and vision diluted by network notes. ABC ultimately rejected it. (Disappointment is a major motivator for Rae; she came up with ABG after thieves broke into her Washington Heights apartment and stole all her camera equipment, along with master tapes of every film and TV project she’d been working on.)

“Color Creative came about because of the pilot process,” she says, “feeling it was archaic, feeling frustrated with how long I felt HBO was taking, and feeling like it’s also really expensive doing $3 million to $5 million for a 30-minute pilot, when we can do a web series for a tiny fraction of that. I just felt like, Not one other writer should have to go through this.”

Much like Jill Soloway, who’s made a concerted effort to hire trans writers and crew members on her Amazon show Transparent, Rae has instituted a similar hiring practice for people of color on Insecure. “HBO never said, ‘You can’t hire writers or women of color,’” she clarifies, “but there’s this thing going on in the industry where there’s an experience factor. ‘There are no writers of color in the room because they don’t have experience’ is an excuse, because how can they get experience if they won’t hire them?”

Most of Rae’s creative team on Insecure are people of color who are stepping into TV roles for the first time, but only after having to work around a lot of red tape regarding Guild rules and union hours. Her showrunner, Prentice Penny, had experience producing Brooklyn Nine-Nine, Scrubs, and Happy Endings, but it was touch-and-go bringing on her main creative partner, Melina Matsoukas, who had never done television before. (She’s known for her world-creating music videos, such as Rihanna’s “We Found Love” and Beyoncé’s “Formation.”) Matsoukas directed the pilot and three other episodes and served as a hands-on executive producer.

Rae calls the show “a mini boot camp for up-and-coming, diverse writers and showrunners.” Every episode is directed by a person of color, from first-timers to veterans like Debbie Allen. “One of our main missions with the show was that it was authentic and the story was being told for us, and by us,” Matsoukas says. She and Rae have had long discussions about the opportunity gap for black people in Hollywood and how that came to be. “There are just not a lot of people of color behind the camera,” she says. “You really have to search and give each other the opportunities. That’s absolutely what Issa did with me.”

Rae wasn’t just producing those opportunities in top positions, but all the way down the crew list. She wanted to hire an assistant director (A.D.) she’d worked with on Awkward Black Girl (“He’s dope, he’s A.D.-ed tons of indie stuff for us”), but found out he didn’t have enough union A.D. experience to work on an HBO set. “In order for us to be able to employ him in the future, he’d have to start over as a P.A.” — a production assistant, the lowest rung of the ladder — “which is insane!” she says. “And just so disrespectful. But he was willing to do that, bless his humble heart.” They went through the same process with costume and set designers. “It’s ridiculous shit you have to endure,” Rae sighs, “to get people caught up in the system.”

Back in the car, we talk about less depressing things, like the people she got to meet at HBO’s Emmys after-party. (“I was fan-girling, like, ‘oh my god,’ Khaleesi! You deserve the throne!”) She reports that Timothy Simons, who plays Jonah on Veep, has a beard and “is actually fine as fuck.” The car drives past a Trump Hotel, and Rae takes a minute to boo it. (“We’re going to throw eggs on it. Tomatoes. Scary.”) Soon it’s back to the Emmys and celebrity couples. She used to love Beyoncé and Jay-Z, “but Lemonade tainted it for me,” and she can’t get behind Rihanna and Drake, “because, like, I deserve him. You know?”

Distractions are good, now that the frustrations of making the show have been replaced with the nerves of people actually seeing it. “It’s so exciting and scary at the same damn time,” says Rae. “But I’m more anxious [for it to be released] than anything. It’s like, ‘Oh, just watch it, or love it or hate it,’ but just be out.

And then, of course, there’s the question of whether the show will get a second season. Rae rolls her eyes, like this is too much for one woman to take. “I’m just like, ‘What will be will be,’” she says. “I know that I am 100 percent proud of what we did, and I’ll go down with the ship.” Besides, she says, “I’m on to the next thing.”