How Issa Rae Built the World of Insecure

The show’s behind-the-scenes collaborations were as important to its success as the bonds portrayed on-screen.

A black-and-white photo of Issa Rae laughing, wearing a floral dress in front of a white backdrop
Coveteur / Trunk Archive

Sitting in a New York City hotel room with a plastic flute full of prosecco and strappy black Manolo Blahnik heels resting near her bare feet, Issa Rae looks like the kind of woman who would have petrified an earlier avatar of herself. If you remember J, the endearingly cringe-inducing protagonist of Rae’s early-2010s YouTube series, The Misadventures of Awkward Black Girl, then you know she was a far cry from the woman who now has her face on magazine covers, billboards across the country, and the festive blue cake sitting on the table in her hotel suite.

Today’s Issa Rae is also a long way from Issa Dee, the cloddish Millennial at the heart of the acclaimed HBO dramedy Insecure, which will end its fifth and final season on Sunday. For much of the series, which draws on Rae’s own travails in her late 20s and 30s, Issa Dee has been, in the simplest of terms, a mess. She has stumbled through infidelity, the protracted demise of a long-term relationship, several more unfortunate romantic entanglements, and a series of unglamorous jobs. Issa Dee certainly doesn’t wear Manolos: In the first episode of Season 5, a thief deems her shoes too tacky to steal.

Insecure’s popularity has always been powered by its candid explorations of career-related ennui, the difficulties of maintaining old friendships into adulthood, and the allure of trying on a new life. The series has been devoted to showing how these everyday trials are experienced by Black characters, even if those characters are sometimes trying to navigate predominantly white corners of the professional world. In the years before Insecure and a handful of other shows debuted in 2016, viewers were unaccustomed to seeing the mundanities of Black life depicted on television; with some notable exceptions, many Black people on TV at the time were either minor characters on white-led series or reality-TV personalities. By filling that void, Insecure became a Black popular-culture phenomenon. Since its first season, it’s driven Twitter conversations that go on for days after an episode airs; it’s been referenced in countless rap lyrics. The phrase broken pussy, coined in the show’s pilot, even inspired frank conversations about vaginal health.

In the first episode of the final season, Issa Dee and her friends travel to Dee and Rae’s shared alma mater, Stanford, for a 10-year reunion. On campus, she looks into a bathroom mirror and sees her college self staring back with youthful optimism and the braces to match. “Oh shit, throwback me?! I forgot how cute I looked with twists,” she says, unprepared for the flurry of questions about to come from her younger self: So what are you doing here? Did we meet T-Pain yet? I know you’re a big-time lawyer now—did you and Molly start a firm together?

The return to Issa’s college years invites reflection on Rae’s own challenges and successes. At 19, having already co-written a feature film, she tried to leave college for Hollywood, but couldn’t convince any industry power brokers that a market existed for the kinds of stories she wanted to tell. Now Rae is among a small cadre of mononymous Black creators whose work is well funded and ubiquitous. Earlier this year, she signed an eight-figure, multiyear film-and-TV deal with WarnerMedia, HBO’s parent company.

Rae told me she felt different producing this final season—and this new self-assurance is evident in the writing. “I’ve literally grown as a person doing this show. I’ve grown in the industry and become more confident about my role in this industry,” she said. “I know who Issa Dee is. I know she’s grown from Season 1 to 5, in addition to my comedic voice.” Dee hasn’t met T-Pain yet, or earned a law degree, but she’s thrown herself into a career she loves that allows her to support emerging artists in her community.

Looking back, it may seem natural that a breezy HBO series about beautiful young Black people in Los Angeles would be a hit, beloved by white as well as Black audiences. But Rae didn’t see that outcome as inevitable. As she has said, with greater clarity and candor as her profile has risen, getting to this level of success was never a guarantee—nor is it something she takes for granted now.

Rae is both an emblem of a sea change in Hollywood that is finally, if slowly, giving resources and power to Black creators, and an agitator insisting on more opportunities at a quicker pace. She is working to ensure that she and a small group of Black peers aren’t the only beneficiaries of a fickle industry’s attention. Insecure’s legacy will likely be as much Rae’s offscreen efforts as the stories she told on-screen.

Issa Rae in Awkward Black Girl.
Issa Rae as J in The Misadventures of Awkward Black Girl (Issa Rae Presents / YouTube)

In 2011, Rae, née Jo-Issa Rae Diop, was 26 and disillusioned by her attempts to make it in Hollywood. So she released a web series on YouTube: The Misadventures of Awkward Black Girl. Rae played J, a young woman who coped with the socially uncomfortable situations of 20-something life in part by rapping to herself—sometimes confrontationally, but always awkwardly. (In a daydream sequence before a date she expects might turn intimate: Hey, pretty boo, ’bout to put it on you / I hope you got protection; we gon’ keep it safe, too.)

The show quickly racked up millions of views and garnered widespread enthusiasm, especially among Black women, who’d been yearning for characters who represented their lives with fidelity and humor. In the 1990s, a brief heyday for Black sitcoms, such characters had been plentiful, but they had been largely missing in popular culture since then. (A college student at the time, I watched the series voraciously, my excitement not even dampened by the implications of many, many people asking me if I’d seen the show about the awkward Black girl.)

The popularity of Awkward Black Girl paved the way for Insecure. Throughout its five-season run, the HBO series, which Rae co-created with the veteran writer Larry Wilmore, has been at its best when it marries the casual comedic brilliance of the earlier web series with the production values that HBO affords it. Like its predecessor, Insecure has captured the terrifying sense of possibility that characterizes life in your mid-20s to early-30s and the anchor that friends can provide amid the turmoil. The series’ most important partnership is the bond between Issa and Molly (Yvonne Orji), a character based on Rae’s real-life best friend. Flanking them are the boisterous Kelli (a criminally underutilized Natasha Rothwell) and the prim, high-strung Tiffany (Amanda Seales). A motley crew of paramours, beginning with Issa’s on-again, off-again love interest Lawrence (Jay Ellis), round out the cast.

When Insecure debuted, the show was perhaps too eager to fill a gap for Black audiences. Some of its early fumbles seemed to reflect an anxiety that it had to make pronouncements about Blackness, or all Black women, which didn’t allow the primary characters room to breathe. While rewatching the early seasons ahead of the Season 5 premiere, Rae noticed how that sense of obligation affected the quality of the writing. “The only times that we would make blanket statements were to me the worst episodes,” she said. “They were the ones where it’s like, Oh, this didn’t hit in the same way, because it wasn’t specific.” In one instantly notorious episode from Season 2, Issa and her friends suggest that Black women are categorically averse to fellatio. That conversation, and a later scene in which Issa responds with laughable melodrama to her sexual partner’s orgasm, elicited a wave of groans from viewers who found it strangely regressive.

Rae was also advised early on to bring in stories that involved white characters, such as Issa’s clueless if well-meaning nonprofit colleague Frieda (Lisa Joyce). Several early-season scenes involved Issa’s frustrations with her white co-workers, who spoke condescendingly about the Black and Latino communities their organization ostensibly served. Had the series focused on Issa’s own posture toward the students, it would have afforded a fascinating opportunity for intraracial introspection. Though Issa struggles financially for most of the series, she’s also a Stanford graduate who was raised middle-class. The show gestured at her class background in some episodes, but never really explored how her relationship to the students might be informed by socioeconomic status. The bumbling white savior was a more familiar trope, and perhaps an easier one for white studio executives to congratulate themselves for green-lighting. As Rae told me when we spoke last year for The Atlantic’s October cover story, those first few years in the industry found her “deathly afraid of losing an opportunity by being a bit too authentic.”

If the series has occasionally missed opportunities to feature diverse Black perspectives on-screen, it has rarely done so off. For many cast members, shooting a series with a creative team and production crew that looked like Insecure’s has been a welcome reprieve from the hostile environments that pervade the industry. Recalling the last days of filming, Rae laughed at how much the experience had spoiled the team. She remembers one cast member saying, “Y’all, I can’t work with white people no more!” Rae shares that sentiment: “I can’t! ’Cause we had such a special experience.”

Across the series’ run, Rae has hired Black writers and directors and cast Black actors in roles they may not have otherwise landed. These aren’t charity cases, Prentice Penny, Insecure’s showrunner, told me, but Rae’s hiring decisions are remarkable in an industry that can still be impenetrable for Black talent. Before Insecure, for example, Yvonne Orji was attempting to break into the business without an agent, a manager, or any acting experience. Rae friended Orji on Facebook in 2008 after seeing a funny video Orji posted, and the two women later struck up a real-life friendship when Orji attended an event Rae organized. “When we were auditioning Molly, she was like, Hey, girl, if you want to come in and audition for that, that would be great,” Penny recalled Rae saying. “Who does that? And that person actually becomes Molly? Not like, Come in and audition for this one line. It was like, Come audition for the lead.”

Issa Rae and Yvonne Orji in Insecure.
Rae, as Issa Dee, and Yvonne Orji, as Molly, in Season 5 of Insecure (Glen Wilson / HBO)

The director Melina Matsoukas came aboard the series in its earliest days. At the time, she had primarily directed music videos (for the likes of Beyoncé, Solange, and Rihanna) and commercials. She’d been looking for a narrative project but hadn’t found anything that spoke to her. Then one of Matsoukas’s agents, who had gone to college with Rae, passed along the pilot for Insecure. “I just related to it so much, as a woman of color navigating through the industry, and so many times being the only one,” Matsoukas told me. “The way she’s able to show and illuminate really beautiful female friendships in her work, I just was like, Oh, this is my life on the page. And then I met her and we spoke the same language, and that was really unique, especially at the time, to find another Black woman creative who had been given this incredible opportunity to tell her authentic story.” Of herself, Rae, and Penny, Matsoukas said: “We call ourselves ‘three the hard way.’”

The trust between Rae and Matsoukas is palpable. You can see it in the bathroom-mirror dialogue between College Issa and her modern-day self. After College Issa notices how good she looks in a braces-free future, she issues a command from inside the mirror: “Lemme see them teeth!” Thus begins a repartee approximating a hip-hop cipher, something of a callback to the Awkward Black Girl rap interludes—except this time Issa’s baring her teeth for her younger self to admire.

The scene “was an improv bit,” Rae told me; Matsoukas understood how Rae works and knew when to let the actor experiment. “Melina was directing that episode. And it reminded me of Awkward Black Girl days a little bit. Because for Awkward Black Girl, sometimes I’d be like, Hey, can you just let the camera run? I just want to try stuff that I know that I can edit together. You may not know what I’m doing right now.

The moment is amusing enough on its own. But it’s especially funny given the pervasive online chatter about Rae’s smile. When I asked Rae if she’d seen tweets like this one—about how her character and an earlier romantic interest couldn’t be together “cause that’s just a lot of teeth in one relationship”—she laughed. “I saw that and cracked the fuck up,” Rae said. “Yeah, it busted me up. I get a lot of teeth comments. And it was something that I didn’t know until making the show.”

Rae’s admitted awareness of the dental discourse notwithstanding, she insists that she’s largely stayed above the Twitter fray that her series has created, and doesn’t make episodes to please fans on social media. “We’ve always been clear in the [writers’] room, like, I don’t want to do shit for Twitter,” she told me.“It is dope as fuck that they talk about it. It is flattering. I love that people get into arguments, good or bad, about things that we’ve done on this show, whether it’s creative, or unintentional … But I can say wholeheartedly that we’ve really tried to block a lot of that out.”

It’s certainly an admirable goal. But in reality, Rae and the rest of the show’s writers have sometimes seemed subject to a too-strong urge to please their audience. As fun as the story lines can be to dissect, those that have felt driven by the fickle predilections of (primarily Black) Twitter have been some of Insecure’s weakest creative choices. In 2017, at the end of Season 2, I lamented that “it has often felt like Insecure has spent more time banking on its viewers’ reactions than it has fleshing out the characters’ stories.”

Penny was more transparent about the effect of social media: He said that he is grateful to see Black Twitter so engaged with the show. “Issa and I never wanted to overstay our welcome,” he told me. “I think Insecure is always best when people are in their feelings about it, for better or for worse.”

Melina Matsoukas, Prentice Penny and Issa Rae on stage at a panel.
Melina Matsoukas, Prentice Penny, and Rae in 2016 (Frederick M. Brown / Getty)

As the show has progressed, it’s thankfully traded in some of the more eye-roll-inducing battle-of-the-sexes fodder (which is catnip for Twitter) for more mature explorations of the show’s primary love story, the friendship between Issa and Molly. The simmering tensions between the two women inspired plenty of strong feelings too, but the stakes of that conflict felt specific and intimate: Each woman’s emotional shortcomings hurt the other. Viewers had seen Molly and Issa grow alongside each other for three full seasons, which made watching them grow apart in the fourth all the more wrenching. Season 5 ties that conflict up quickly in its premiere, which allows Rae and Orji to return to the onscreen partner work that propels Insecure (and for which Orji has garnered a wealth of attention and opportunities). The resolution also serves as a reminder that such chasms between friends need not be irreparable, especially in the face of life’s larger challenges. In the premiere, when Molly asks Issa, “Are we gon’ be okay?,” the latter is quick to inquire whether the question is about their friendship or the world. The reference to our dystopian times is pointed enough to land, but it’s also subtle enough to dissipate gently into a scene about partying with the girls.

On a recent Wednesday afternoon in New York City, Rae was waiting for filming to begin on one of the latest projects from her media company, Hoorae. Rap Sh!t, a half-hour comedy series about two high-school friends who reunite years later to form a rap group, directly merges Rae’s production experience with her musical inclinations. The show is written by Rae, who also serves as an executive producer, and Hoorae’s audio arm, Raedio, is handling the music supervision.

With the sun beginning to set and the temperatures dipping, the cameras started to roll much later than planned. Rae and the Rap Sh!t showrunner, Syreeta Singleton, stared intently at their screens. The writer Kid Fury, best known as a co-host of the popular podcast The Read, was nearby. Maybe 50 yards away, the show’s leads, Aida Osman and KaMillion, waltzed out of a car and up to the front of the line for a Spotify party that had been staged at the entrance of a Brooklyn hotel. The actors moved with both the braggadocio and the anxious overperformance that early-career rappers like their characters would carry into that kind of music-industry event. They want everything recorded; they were probably on Instagram Live before they even opened their car door.

Rae and Singleton watched Osman and KaMillion rehearse the scene repeatedly, laughing. They conferred, and relayed their feedback to the producer who was running commands back down to the actors. Their note was simple: Osman and KaMillion were doing great, but the scene needed more bad-bitch energy. It’s the kind of directive that might sound ridiculous in a different setting, but here everyone in earshot nodded knowingly. The actors took a beat and ran the scene back, this time with even more gusto.

Quick-witted yet thoughtful, Osman, 24, also serves as an executive story editor for Rap Sh!t. She’s part of a growing, loosely connected group of young Black creatives in the Los Angeles area who all have one thing in common: “Some of them are graphic designers, some of them are record producers, some of them are rappers and singers,” Osman told me. “And in some way, shape, or form, all of them are contributing to art and getting paid thanks to Issa and Hoorae and all the people at Hoorae that are making so many opportunities for us.”

She recalled a time when she was working on a Rap Sh!t script while a friend in a different room was trying to get a song placed on Insecure and another friend was making graphics for an Insecure writing camp. “I was like, ‘Are we all just working for Issa? Is that what’s going on?’” she said with a laugh.

Rap Sh!t has become Rae’s latest means of honing her creativity through collaboration. Though she told me she wants the show to feel different from anything she’s done before, it will inevitably be powered by her keen attention to the talents of the people surrounding her. For Rae, seeing potential in others isn’t just a way to bolster their careers; it’s also part of how she propels herself and her own work forward: “That comes from a natural desire, even a Drake desire,” Rae told me, referencing the chameleonic rapper she’s been shouting out since well before her success put her in the same stratosphere. “Like, I see what you’re doing, and I’m not co-opting it, but I want to boost it. It’s dope that you’re doing that, and maybe in seeing you doing that, it’ll rub off on me in a way that can take me to another level.”