The multi-hyphenate mogul refused to center white people on Insecure. And she won’t do it anywhere else, either.
I spent a week preparing to interview Issa Rae as she prepared to launch the fifth and final season of Insecure. Much of that time was spent imagining how much fun we would have together. Our meeting would be a dream come true for my 21-year-old self, who regularly gathered his friends in a dorm room nearly a decade ago to huddle around a 13-inch laptop, pull up YouTube, and watch episodes of The Misadventures of Awkward Black Girl.
I assumed Issa and I would have a lot in common, from our shared ability to make any situation uncomfortable, to our tendency to process our feelings in the form of mirror raps. My plan was to arrive in Miami, where Issa is currently stationed while working on her upcoming HBO Max project Rap Shit, a half-hour comedy about two high school friends who start a rap group. I’d brandish a bottle of mid-to-high grade champagne, and Issa would produce a vape from her small designer handbag. As we became increasingly intoxicated, she would tell me the secrets of making it in the industry, dishing on her wild and crazy life, her glamorous adventures with her handsome new husband, and her gaggle of hot friends. As we enjoyed a feast of tacos — her character on Insecure seems to love tacos — we would exchange dick jokes. You’re hilarious, she’d say, in a puff of laughter and smoke.
Instead, I arrived at M3 Studios in Miami Springs to find Issa standing in a hallway, clad in a plush, fuschia bathrobe, looking down at her cell phone as a group of electricians laid wires around her. We walked to an adjacent room, and I mentioned how I regretted not bringing a bottle of champagne. “Thank you,” she says with a polite smile. “But I’m so glad you didn’t.” She was taking a break from alcohol and wouldn’t have indulged anyway.
The person before me, I quickly remembered, wasn’t Issa Dee, the listless twenty-something I’d grown to love over five years and 34 episodes of television. This was 36-year-old Issa Rae, the hyper-focused actress, producer, and entertainment mogul. She would not be sharing a vape with me. Instead, as we sat in a secluded corner of the studio while the photographer’s crew set up, I had the privilege of deconstructing the mythology of someone I’d looked up to for years.
I first met Issa Rae in 2011 at Kenyon College, where I’d binged endless episodes of her web series. To promote the successful first season of Awkward Black Girl, she and her team launched a college tour. As president of my school’s Black student union, I blew $3,000 of our meager budget to fly Issa and her co-producer Tracey Oliver, the writer of Girls Trip, to rural Ohio.
I skipped a creative writing class so I could pick them up from the airport and drive them for miles on the two-lane farm road that eventually led to campus. They talked about their work to an audience of no more than 40 people in the library’s basement screening room, and Issa spoke about her ambitions to see her story told on HBO. I watched, rapt, knowing deep in my soul that they were on to something big. Of course, I was right.
A lot has changed since then. Rae, for one, has grown up. And so has television — spurred by pressure from streaming services, independent creators on platforms like YouTube, and a growing acknowledgment of the many ways that American media often fails its Black viewers — it has finally become a medium where creators like Rae can not only survive but thrive.
A few days before our meeting in Miami, The Atlantic published one of the most comprehensive articles ever written about the “unwritten rules of Black TV”, conventions that have existed and went virtually unchallenged since Sanford and Son premiered in 1972. Writer Hannah Giorgis explains that for decades, Black television writers were tasked with producing “negotiated authenticity … Blackness, sure, but only of a kind that is acceptable to white showrunners, studio executives, and viewers.”
“Tattoo this article on my back,” Rae tweeted about the piece.
The power of Giorgis’s story, to me, is the skill with which she traces a clear line connecting decades of Black television creators. How Sanford and Sons opened the door for The Jeffersons; how The Cosby Show made way for A Different World; how Girlfriends was a training ground for Insecure’s executive producer, Prentice Penny.
“What I loved especially about that piece was that it just pointed out whose shoulders I'm standing on,” Rae says. “It was like seeing your television ancestors all in one place.” Citing Debbie Allen’s choice to tackle the issue of race head-on in A Different World, a departure from Bill Cosby’s original intention for the series, she says, “I’m just proud of the little protests that everyone has had to do to enable us to do us. I hope that we're brave enough to be able to carry that through.”
Though Rae is a multi-hyphenate creative, it is clear within moments of speaking with her that her first love is television. In many ways, her success can be attributed to her deep understanding of not only TV, but social media, online community building, and the distinct way stories are told online. She quickly became one of YouTube’s earliest crossover success stories. When she began developing her web series for television in earnest — first in 2013 as a Shonda Rhimes-backed project called I Hate LA Dudes, and then with HBO in 2015 — she was well-versed in both the language of Black Twitter and of television board rooms, and uniquely positioned to usher in a new era of Black millennial stories on television.
A key component of Insecure’s success has been the voraciousness with which its audience of mostly (but not entirely) Black internet users amplify the show across social media whenever it airs. The show’s award-winning and oft-written about #InsecureHBO social campaign brings millions of people — almost 11 million, per one report — into a conversation about the show and its stars each week. Comments range from Black Twitter’s particular brand of wit, to poignant reflections on the show’s storylines, to a running joke that the episodes should be expanded to a full hour. But the conversation isn’t all levity; Twitter is also a space where the Insecure audience can unfairly criticize Issa Rae’s appearance, obsess over minor plot details, and project their hopes for all of Black television on the creator.
Issa Rae’s ambitions know no bounds. “I want to do what Disney and Oprah did. I want that.”
“I knew the onus was going to be on us to represent all Black women because we just didn’t have a lot of shows featuring Black women then,” she says. Comparing her experience with that of a predominantly “white show” like Big Little Lies, she continues, “Nobody's coming for Nicole Kidman like, ‘Bitch, you don't represent every white woman. Fuck you.’” But such is the “special scrutiny” of Black work. “Every Black show gets it. Every Black piece of work gets scrutiny because we’re sensitive about our shit.”
“I said from the jump during the promo tour: ‘This is a very specific Black female experience — it's my specific one — we cannot represent all of that.’ And even now people are still like, ‘This doesn't represent me, this is not it, this is the only representation that we have,’ and I realize that's just a constant complaint with whatever you put out.”
Rae has realized that this special scrutiny applied to her personal life as well. Her social feeds feel like dispatches from a friend — the kind of friend who would make a video gently asking Rihanna or Beyonce not to release music so they don’t steal her shine. But rarely do we get glimpses into her personal life. Many people didn’t even know Rae was dating, so when the actor revealed a series of photos from her July 25 wedding to longtime boyfriend Louis Diame, Black Twitter ignited with both shock and praise.
Until this point in our conversation, we had mostly talked about her professional life and creative work. She visibly tensed a bit as the conversation became more personal. After a nervous laugh, Rae admitted that releasing the photos felt like a major step. “There was a reason why I felt compelled to share,” she says. “ It was going to get out anyway, so I was just like, ‘Let me share it my way.’”
Rae received overwhelmingly effusive feedback from millions of followers across her social media platforms when she shared her wedding images. Then the criticism began. “I wonder why Issa Rae hired a white photographer for her wedding and not a Black one? I thought you were ‘rooting for everybody Black’?” read one tweet, referencing a much-memed phrase from her 2017 red carpet appearance at the Emmys.
In a brief moment of vulnerability, Rae admits to me that, yes, sometimes, this stuff gets to her. But she quickly turns defiant: “No matter what I do, there's going to be a negative conversation on it.” Taking a moment to consider her words, she continues, “You can't please everybody, and I don't want to please everybody. I actually want to piss people off. That is my motivation.”
Perhaps the most significant thing about Insecure is the way that, in increasing measures through each season, it refuses to center its world around white people — a unique privilege for a Black TV show.
When I ask Rae about the lessons she hopes to pass to people of color who want to follow in her footsteps, she launches into the role of the white gaze in her work: “From the jump in creating the show, it was put in my mind that you had to have a white character to be a bridge, and for people to care, for it to get awards, for it to be considered worthy of the television canon.”
In Awkward Black Girl, one of the two main love interests is White Jay, a white man that Rae’s character spends the first season in a will-they-or-won’t-they back and forth. She tells me that the character was added at the advice of a colleague.
“She was just like, ‘Girl, if you want this shit to set off to the next level, you got to put a white character in there, then white people will care about it, then NPR is going to write about your shit, and it'll blow up,’” Rae tells me. “And then it literally happened.” This thinking stuck with her as she began to develop Insecure.
In the show’s first three seasons, Issa works for a not-for-profit called We Got Y’all, an organization with a one-of-each diverse staff and a murky mission. Early iterations of the show heavily featured Freida, Issa’s white coworker, and friend. This provided an early challenge for the creative team: Should we make sure that she's featured, so that there's a bridge for white people?
“And I was like, Fuck no! This is not a show about Freida!” Rae says. “That was when I started actively resisting. When Issa quit work and we got rid of the We Got Y'all storyline, I realized, ‘Oh my gosh, our show is just about Black characters now in the most refreshing way.’”
Now Rae has a rare freedom that, in the past, Black television creators could have only dreamed of. Her conversations with HBO were never "Let's break it down for white people” or “What does this mean?” she says. “They would always kind of just let us do us, and trusted us in the best way, and for that, I’m spoiled.”
I tell Rae repeatedly that I believe we’ve yet to see the full extent of Insecure’s impact on culture. Like that ancestral line from A Different World to Girlfriends, it might take years before the long-term results of The Issa Effect take root. The writers and directors who cut their teeth on her show will undoubtedly go on to make a discernible mark on the entertainment industry that will be felt for decades to come.
Unlike in 2011, when Rae’s web series premiered, there are now so many shows about young Black people on TV I couldn’t possibly watch them all: Atlanta, I May Destroy You, Two Dope Queens, Abbot Elementary, The Black Lady Sketch Show, Dear White People. Five years after its premiere in October 2016, Insecure leaves a much different television landscape than it entered. HBO has produced multiple series helmed by Black women, thanks in large part to the example set by Rae’s work. For both executives and aspiring creators, the door for Black people hoping to make work is open wider than it's ever been. And Rae’s ambitions know no bounds: “I want to do what Disney and Oprah did,” she says. “I want that.”
As we talk about the future, I see a familiar look in her eyes: defiance. “I want to be able to circumvent all that bullshit when an executive’s telling you, ‘This won't sell,’ or, ‘If this is a Black story about a family, it has to have trauma,’” she says.
“I hope that not having to think of an audience that isn’t us — and being okay with that— is passed on,” she tells me. “I want people to know we are enough.”
Stylist: Jason Rembert
Makeup: Joanna Simkin
Hair: Felicia Leatherwood
Executive Producer: Shanté Cosme
Line Producer: Juliana Zanon
Production Designer: Damian Fyffe
Stylist Assistant: Reginald Keaton-Reisman
Art Assistant: Max Moupia, Luís Roman
Tailor: Matthew Reisman
Manicure and Extensions: Sherwin Hora
Bookings: Dan Resnick