Somewhere, during the elaborate chorÂeography leading up to my initial meeting with Issa Rae, a miscommunication between her publicist and me led to my asking Rae how the filming of her pilot was going. Rae pressed her chin to her chest and rolled her eyes upward, making the universal face for: ‘‘Are you kidding me?’’ Actually, she explained, the show had no director attached, no pit crew, not even the slightest inkling of a cast. She was nowhere near filming. All she had was a finished script and a charged cellphone.
It was a sweltering March morning, and we were sitting in her office in Inglewood, Calif., a small and efficient affair just a few blocks from where she grew up. It’s little more than a couple of nearly empty rooms, mostly used for meetings â€" that is, when Rae has meetings to take. She pulled out a box of Frito-Lay snack packs and offered me one.
Rae, who is 30, was fresh off a photo shoot for the May issue of Essence magazine. It had anointed her, per the cover line, a ‘‘game changer,’’ alongside some of the biggest names in television and film, including Shonda Rhimes and Ava DuVernay. Two years ago, HBO hired Rae based on the viral success of her YouTube show ‘‘The Misadventures of Awkward Black Girl,’’ which she wrote, directed and starred in. The first episode alone attracted almost two million views by serving up a slice of black life not often available on-screen â€" a quirky, misanthropic main character, like Liz Lemon but with more melanin.
Rae looked at her phone briefly, then asked me if I’d read a story published that day on the website Indiewire. It was a sort of census of TV pilots, and it found that 73 were in the works featuring black actors in major roles. Included in that tally was the show Rae is developing for HBO, tentatively titled ‘‘Insecure.’’ But her part as the lead character was the only one she’d been able to cast. People had warned her that television is notoriously slow, but it has been excruciating for Rae, who built her career ad hoc, out of her bedroom.
Recently, the critical and commercial success of shows like ‘‘Black-ish’’ and ‘‘Empire’’ has demonstrated to Hollywood executives that the public is hungry for complex characters of color. Now they must figure out how to bring them to life. In a way, whether Hollywood can adapt to creators like Rae will be a litmus test for how seriously it takes black entertainment.
I had seen the story on Indiewire, and mentioned that 73 seemed higher than I expected. Rae slowly nodded, tempering her optimism: ‘‘It still feels like we need to be in charge to prioritize story lines. Behind the scenes, it can be very white.’’ I asked if she thought that mattered. ‘‘I think so,’’ she said. ‘‘Otherwise, it could just be a trend.’’
A few days later, Rae took me for a ride past the strip malls, drought-parched lawns and stucco houses that make up View Park-Windsor Hills, the South Los Angeles neighborhood where she spent her formative years. She bounced giddily in the driver’s seat as she reeled off a list of beloved black movies and television shows set in the area: ‘‘Boyz N the Hood,’’ ‘‘Moesha,’’ the rom-com ‘‘Love and Basketball’’ and the TV show ‘‘Girlfriends.’’ These movies and shows captivated Rae when she was young, not because they were shot near her but because they offered a glimpse of how black lives could be depicted on-screen. They felt real to her, textured, authentic creations.
Windsor Hills is also known for being among the wealthiest black neighborhoods in the country. Rae drove us by a low-slung ranch house that, from the outside, appeared to have a generous rec room, and a palatial white home that Rae said had probably been added to since she lived there. They were just a couple of blocks apart, and she spent two large, but very separate, portions of her childhood in them.
Her mother, Delyna, is from Louisiana, and her father, Abdoulaye, is from Senegal. They met while studying in France, started a family, then moved around a lot before briefly settling with their five young children in Windsor Hills in the ’80s. Adboulaye, a doctor, was working to build a pediatric clinic in nearby Inglewood. His clinic is still there, on the corner of West Manchester Boulevard and South Seventh Avenue. Rae took me by it as part of her tour, and the building bears his name in 1,000-point font: A. Diop Family Care Medical Group. (Issa Rae’s full name is Jo-Issa Rae Diop.) The family fell into an exceptionally average life, until escalating gang violence unnerved Rae’s mother. She insisted that the family relocate to Senegal, and Rae’s father agreed; living in Africa would also instill his children with discipline and respect for their heritage.
In 1988, they moved to a lavish home, kitted out with a security guard and a maid, in an upscale neighborhood in Dakar â€" the capital and Abdoulaye’s hometown. Rae’s father tried and failed to open a hospital there, and after about two years, the family moved back to Windsor Hills. Rae’s mother enrolled her in one of the best schools in South Los Angeles, King/Drew Magnet High School of Medicine and Science.
Until then, Rae had zigzagged between private schools, where she stood out for being black, and public schools, where she was mocked for her so-called white affectations. King/Drew was largely black and Latino, and she relished her immersion in mainstream American black culture, which until then she had mostly experienced through TV. Rae calls it her ‘‘pinnacle black experience.’’ It was also here that she began taking acting seriously. King/Drew’s drama department often staged complex and challenging narratives about race; Rae participated in a production of ‘‘On Strivers’ Row,’’ a 1939 play about class conflict among Harlemites.
Rae went to Stanford University, where she majored in African and African-American studies. She found the drama department to be bland in comparison with King/Drew’s, but she continued acting and directing outside it. Inspired by a classmate who’d written and produced a D.I.Y. hip-hop opera, Rae started working on a project of her own: a stage adaptation of Spike Lee’s ‘‘School Daze.’’ It attracted a packed house. Rae realized she liked writing and producing â€" as well as the feeling of bypassing gatekeepers.
A 20-minute drive from campus, in a makeshift office above a Japanese restaurant in San Mateo, Chad Hurley, Steve Chen and Jawed Karim were developing a video-sharing website called YouTube. When Rae first discovered the site, she mostly used it to watch old ‘‘American Idol’’ clips. Soon she started to make raunchy music videos with her friends and classmates for parody songs they wrote, like ‘‘Working the V’’ and ‘‘Nani Pop.’’
During her senior year, she recruited friends to star in a soapy, low-budget mockumentary series she wrote about student life at Stanford called ‘‘Dorm Diaries.’’ The series alternated between vignettes of action and confessionals, like those on MTV’s ‘‘Real World.’’ But unlike the cast of that show, which tends to include one or two black characters per season, Rae’s actors were all black. Rae posted episodes of ‘‘Dorm Diaries’’ to Facebook, and the show quickly circulated around her campus. From there, it spread to others, like Georgetown and Harvard. Rae learned that she had a knack for portraying everyday black life â€" not made special by its otherness or defined in contrast to whiteness, but treated as a subject worthy of exploration all of its own. ‘‘It was a light bulb, my epiphany moment,’’ she says.
After graduating in 2007, Rae got a fellowship at the Public Theater in New York. She planned to pitch ‘‘Dorm Diaries’’ to MTV or BET. Then, one night, thieves broke into her Washington Heights apartment and stole thousands of dollars’ worth of equipment, including her laptops, camera and all of her tapes. Even her scripts and the pitch reel she was polishing for the networks were taken.
The burglary left her in debt and depressed; you can’t make movies without equipment. Still, she forced herself to attend film networking events. She found them absurd and torturous, especially for an introvert (which Rae likes to claim she is). After a particularly excruciating gathering, Rae was sitting on her bed in her apartment, drawing in her journal. She scrawled out the words: ‘‘I’m awkward. And black.’’ Rae liked the way they challenged the archetypes generally available for black people in entertainment, especially women, who are often cast as sassy, power tops, angry or motherly figures â€" sometimes a combination of them all â€" but rarely awkward. This thought process led her to create a character that, much like Rae herself, defied these stereotypes: a woman at home in her blackness, but shy, who grappled with her identity, and who loved rap music but couldn’t dance to it to save her life. This sketch became the basis for her alter ego, J, the protagonist of ‘‘Awkward Black Girl.’’
In Rae’s best-selling memoir, also called ‘‘The Misadventures of Awkward Black Girl,’’ published earlier this year, she writes about her discomfort with ‘‘Precious,’’ the critically acclaimed 2009 movie about an abused, illiterate, pregnant black teenager. It is punishing to watch; in one of its most vivid scenes, Precious steals and eats a bucket of fried chicken and then vomits into a trash can. Rae felt uneasy ‘‘not because I disliked the film, not because I couldn’t relate to the story, but because Hollywood was so [expletive] excited about this movie,’’ she writes. ‘‘Is that what it takes to create a sympathetic black female lead character?’’ In a sense, it is this question that has animated Rae’s short career in television writing.
One episode of ‘‘Awkward Black Girl,’’ titled ‘‘The Job,’’ encapsulates the show’s seamless blend of race politics and Seinfeldian situational comedy. On the show, J works as a telemarketer for Gutbusters, a dubious weight-loss-supplement company in Los Angeles, and in this particular episode, she cuts off all of her hair after a boyfriend dumps her. J’s boss, an older white woman, becomes fascinated with the haircut, asking a series of rapid-fire questions: ‘‘Do you wash it?’’ ‘‘Can you wash it?’’ ‘‘Can I touch it?’’ J’s eyes widen in disbelief as she fantasizes about a variety of ways to shut her up, including smushing her boss in the face and yelling ‘‘Stop!’’ Eventually, she is required to attend anger-management counseling, which allows her to grow closer to another attendee: a gentle blond man named Jay (christened White Jay by fans, a name that stuck).
Part of the sly genius of the show is that viewers are let in on J’s interior monologue â€" the show leans heavily on voice-over â€" and much of the humor comes from the tension between her self-image and the impression she makes on others, who generally struggle to reconcile all of the seemingly incongruent aspects of her identity. In one episode, after J sleeps over at White Jay’s house and borrows a clean shirt from him, a new receptionist gives J’s short Afro and baggy clothes a knowing smirk, and invites her to an L.G.B.T. support group. J scrambles to come up with a way to say she isn’t gay without causing offense, but she can’t find one, so she reluctantly accepts the invitation.
Rae grew up in the ’90s, which is sometimes called the golden era of black television. Many of the most memorable shows on TV that decade â€" ‘‘The Fresh Prince of Bel-Air,’’ ‘‘Family Matters,’’ ‘‘Martin,’’ ‘‘In Living Color,’’ ‘‘Sister, Sister’’ â€" starred black actors and were written by black writers, and many had long runs on major networks. Some smaller networks had entire lineups that skewed black, too: Fox, UPN and the WB in particular. But this era was short-lived. Kristal Brent Zook, the author of ‘‘Color by Fox: The Fox Network and the Revolution in Black Television,’’ says that the collapse was caused by these networks tacking toward the mainstream. In the mid-’90s, Fox started to model itself after the Big Three networks. ‘‘Once they had the means to move up in the world, they didn’t need the African-American viewer anymore,’’ Zook says. ‘‘In 1994, they just canceled the majority of black-produced shows in one fell swoop.’’ UPN ended up in CBS’s portfolio and was then merged with the WB to form a new station called the CW, best known for ‘‘Gilmore Girls.’’
Black television was a lifeline for Rae, especially during a period of her childhood spent in Maryland. ‘‘When I was in Potomac as the sole black girl, these shows were my access to black culture in some ways,’’ she writes in her memoir. ‘‘When I moved to Los Angeles, and the kids said I talked white but had nappy hair, I found a sort of solace in knowing that Freddie from ‘A Different World’ and Synclaire from ‘Living Single’ were napped out, too. I could be worse things.’’ Freddie and Synclaire were free-spirited black women who could be described in many ways â€" artsy, oddballs, sporty, cultivators of strange hobbies and affectations â€" and yet were unequivocally and undeniably black.
As she grew up, Rae became disillusioned by the rise of catty reality-television tropes and token stock characters. She describes them in her book as the ‘‘extremely tragic black woman, or the magic helpless Negro, or the many black men in dresses.’’
‘‘How hard is it to portray a three-dimensional woman of color on television or in film?’’ she writes. ‘‘I’m surrounded by them. They’re my friends. I talk to them every day. How come Hollywood won’t acknowledge us? Are we a joke to them?’’
Her own show was an instant hit online in 2011, and soon a number of networks and production companies expressed interest in adapting ‘‘Awkward Black Girl’’ for prime-time TV. To Rae’s disappointment, most wanted to completely rework the show. Rae recalls a phone conversation with a network executive who wanted to make it into a pan-racial franchise operation, starting with ‘‘Awkward Indian Boy.’’ Another suggested Rae recast the lead with a lighter-skinned actress with long, straight hair â€" in essence, the exact opposite of Rae. She turned down the offers.
‘‘They wanted to make it as broad as possible, broadly niche, but I was like: No, that’s not what this is about,’’ she says. Another botched opportunity came in the summer of 2012 with Shonda Rhimes and Rhimes’s production partner, Betsy Beers. Rae pitched them a show called ‘‘I Hate L.A. Dudes,’’ a comedy about a woman trying to date preening, image-obsessed men in Hollywood. Rhimes and Beers loved it so much that they sold it to ABC. But Rae had trouble getting the script ready for pilot-reading season that winter. She recalls fielding constant, sometimes overlapping and contradictory notes from the network and Rhimes’s team. (Rhimes declined to be interviewed for this story.) In the end, her treatment fell short of expectations, and the pilot wasn’t picked up. ‘‘I compromised my vision, and it didn’t end up the show that I wanted,’’ she says. ‘‘It wasn’t funny anymore.’’
While Rae grappled with the pressure to dilute her sensibilities to find mainstream approval, Silicon Valley would once again intervene in her favor. The rise of digital streaming over the past few years has altered the calculus of representation in television. Broadcast networks are no longer the sole creators and distributors of shows; a vast array is being produced by media and technology companies, including Snapchat, Yahoo, Hulu and Amazon. Even premium networks like Showtime and HBO have introduced stand-alone digital products to appeal to younger viewers and have shifted their focus to making original programming â€" which, in the long run, may drive subscriptions. This shift allows â€" and encourages â€" the creation of bold, nontraditional programming that can be aimed at specific audiences instead of the broadest market possible.
In February 2013, Rae received a call from Casey Bloys, executive vice president of programming at HBO, who wondered if she had any other ideas to pitch. She eventually came to the network with the concept for ‘‘Insecure.’’ It’s about a woman on the brink of turning 30 who is wrestling with the onset of her delayed adulthood. She would be played by, and loosely based on, Rae.
Rae happened to share a management firm, 3 Arts, with the actor and writer Larry Wilmore, and it arranged for Wilmore to walk her through the screenwriting process. Before he joined Comedy Central, Wilmore had a hand in practically every black television show of note: ‘‘In Living Color,’’ ‘‘The Fresh Prince of Bel-Air,’’ ‘‘The Jamie Foxx Show,’’ ‘‘The Bernie Mac Show,’’ ‘‘The PJs,’’ ‘‘Sister, Sister’’ and even the short-lived ‘‘Whoopi.’’ He spent a month interviewing Rae. They would sit for hours on his building’s rooftop in downtown Los Angeles. ‘‘I asked her what was going on in her life, what’s important to her, her sex life, what she thinks about, and we built the show out of that,’’ Wilmore says. ‘‘She had the ideas for characters, and we created a world around them.’’ They wrote the first script in eight days and revised it over the following weeks.
HBO approved the script for ‘‘Insecure’’ in the fall of 2013. Rae was excited to hire a support staff of other nonwhite writers and producers who would be intimately familiar with the milieu inhabited by her characters. She had a wish list of people she liked â€" primarily young women of color â€" but she soon found out HBO had little interest in hiring them. Generally, an HBO spokeswoman said, the network wants people who have experience.
By this March, Rae was eager for some forward momentum but still wary of ending up with the wrong team. She knew she needed a showrunner who would be amenable to her vision and polished enough to please the networks. Chris Rock had expressed interest in directing the pilot episode of the show, but he wanted to shoot it in New York. This would have been convenient for him but would have undermined Rae’s desire to depict her Southern California home. (Rock declined to comment.) Eventually, HBO offered a promising candidate: Prentice Penny, a black showrunner with a reputation for his work on ‘‘Scrubs,’’ ‘‘Brooklyn Nine-Nine’’ and the colorfully strange ‘‘Happy Endings.’’
Shortly after our conversation in her office, Rae and I drove to a gastropub in Culver City, where she and Penny were scheduled to meet. We were shown to a booth in the back of the restaurant, an industrial-chic joint with exposed steel piping. As we waited for Penny to arrive, Rae fidgeted, obsessively smoothing out her checkered button-down shirt. She was nervous; a lot was riding on the meeting. A few minutes later, Penny breezed in, looking every bit the part of a successful Hollywood writer, with the kind of dewy skin that comes from expensive moisturizers and a visibly sculpted physique beneath a fitted periwinkle shirt and stylishly tapered sweatpants.
He sat down, summoned the waiter and ordered a Manhattan. Then he told Rae that he had a message from Mara Brock Akil, the creator of the UPN sitcom ‘‘Girlfriends,’’ which gave Penny his start as a writer. When she heard that he was meeting with Rae about her show, she gave him a stern warning: ‘‘She said, ‘Don’t [expletive] it up! Get this black girl’s vision right.’ ’’ Both broke into laughter. Penny continued: ‘‘I told her, ‘That’s easy!’ ’’
Penny asked Rae where she grew up, and when she told him, his face lit up in recognition. He knew Windsor Hills well, and they played that classic Southern California name game of intersections and boulevards. Rae sat back in the booth, a beatific grin spreading across her face. ‘‘That’s the neighborhood I want to depict,’’ she said.
Rae and Penny ordered food and talked about how they’d handle some of the scenes in the treatment. In one scene, Rae’s character is dumped and goes on a bender; in another, she and her best friend, Molly, have a philosophical discussion about Marge Simpson. He told her to focus on the relationship between the two protagonists. ‘‘People will watch if Molly and Issa have chemistry,’’ he said. Penny pushed Rae to think about the vibe of her show: its look (polished or gritty?), the pace (quick cuts or slow-moving scenes?) and even the color palette (washed-out or glossy?). He said it would be important to differentiate her show from HBO’s other female-centric offerings, to increase not only its chances of being picked up for a full season but also the likelihood of a renewal for a second season. And renewal is the goal, he said â€" there’s no surer sign of success in Hollywood.
‘‘Insecure’’ will deal with race and cultural identity directly, so Penny encouraged Rae to think creatively about how she might portray the duality between what he described as ‘‘the internal and external Issa.’’ Despite some writers’ ambivalence about voice-over, Penny praised her use of it, especially on ‘‘Awkward Black Girl.’’ One of Rae’s strengths as a writer is her ability to wring comedy out of the peculiarity of the black experience in America, specifically what W. E. B. Du Bois called ‘‘double-consciousness’’: the sense that you’re always looking at yourself through the eyes of others, and trying to pre-emptively understand what judgments and opinions they may be making about you at any given moment. Penny seemed to understand this. ‘‘These are the things that we as black people think and feel and can’t say,’’ he said. ‘‘It’s the fine line we all walk.’’
Lena Waithe, a producer of the recent movie ‘‘Dear White People,’’ thinks a coming cluster of TV shows, including Rae’s, will broaden the types of stories being told about black America. ‘‘She was at the beginning of the wave of creators, black millennials who don’t fit into either stream,’’ she says. ‘‘They don’t come from the ’hood, but they aren’t the Huxtables.’’ She pointed to Jerrod Carmichael and Donald Glover, two black comics whose pilots were recently picked up. ‘‘There are black people on television, but they’re still painted with broad strokes,’’ she says. ‘‘We don't have characters painted with tiny paintbrushes.’’
Rae’s desire to render her world accurately has pushed her to be particular about her hiring decisions. To direct her pilot, Rae signed on Melina Matsoukas, best known for her lush art direction on music videos, including Rihanna’s ‘‘We Found Love.’’ At a casting session in July, Matsoukas and Rae were auditioning a woman for the Molly character. Molly is modeled on Rae’s real-life best friend, a corporate lawyer who grew up in South Central and can flawlessly toggle her speech patterns and behaviors to suit her environment. Rae didn’t quite know how to ask the actress to act more ‘‘street,’’ but she needed to see if she could code-switch with the same dexterity as her friend. Matsoukas tried to guide the actress through it, and she fumbled despite the coaching, helping Rae realize she might not be the right person for the role.
As Rae sees it, the lack of diversity in writers’ rooms makes it hard to develop complex characters of color on-screen. Her solution is to bring more people of color into the television-writing pipeline, so she spends much of her free time working on Color Creative, a digital platform she co-founded for minority writers. She helps produce and find funding for their web shows, and offers aspiring writers a place to showcase their work. She started the organization, in part, as a response to her own difficulties with the network pitching process. ‘‘I don’t ever want it to be just me, ever,’’ she says. ‘‘That is the worst feeling, to be alone, because then all the pressure is on you. People expect you to be the voice of everyone.’’
As Penny and Rae finished their meal, Penny told her stories from his decade-long career, in which he was, more often than not, the only black person in the writers’ room. In 2000, he made a film about the way men and women interpret milestones in relationships. Its working title was ‘‘You Say Tomato,’’ but his production company wanted to package it better for a black audience. Rae erupted with laughter as he dropped the punch line: The movie was eventually released as ‘‘Soul Talkin’.’’
Throughout the arc of his career, Penny explained, he has often found himself in situations that required a delicate touch, and he stressed the importance of staying professional in uncomfortable settings. His anecdotes and advice added up to something like a guide to navigating Hollywood while black. Rae listened, rapt, drinking in his words. He later summarized his philosophy to me this way: ‘‘Make sure you’re professional, and your stuff is tight. Have it together. You can’t ever look like you are not on your game. As a writer of color, be strategic, and be careful.’’
The check came, and Rae picked it up. Before they left, they lingered, seemingly reluctant to say goodbye. Eventually, Penny grew serious, offering words of motivation. ‘‘I want you to win,’’ he said. ‘‘If you win, another Issa wins. And another, and another.’’
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