Issa Rae’s Next Chapter: How ‘Insecure’ Creator Is Becoming a Media Mogul With Production Banner Hoorae

Angelique Jackson
·17-min read

On the red carpet at the 2017 Emmys, Issa Rae told Variety, “I’m rooting for everybody Black.” The interview went viral, with memes, GIFs and unauthorized merchandise featuring her one-liner flooding the internet.

It was a candid moment for the multi-hyphenate star, but her actions back up the sentiment. From the stories she tells on-screen to how she promotes and has launched Black-owned businesses and, most evidently, in the talent she works to elevate, Rae is indeed rooting for everybody Black and using her celebrity to make that possible.

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So, when Black Lives Matter reached out to Rae last summer to create a line of T-shirts using her quip as a slogan, she was quick to greenlight the project.

“I had never officially made ‘Rooting for Everybody Black’ shirts and loved the idea of partnering with them for an intentional cause,” Rae tells Variety of the collaboration, which has raised $12,000 for BLM since the campaign’s Feb. 15 launch.

Over the past decade, Rae has gone from digital darling to Peabody Award-winning TV creator to film star, and as she transitions to the next level in Hollywood, her sphere of influence only gets larger. As they say in “Spider-Man,” one of Rae’s favorite pieces of pop culture, “With great power comes great responsibility.”

On Jan. 13, the writer, producer and star of HBO’s “Insecure” announced that the hit comedy series would wrap with its upcoming fifth season. Then, Feb. 3 marked the 10-year anniversary of her groundbreaking web series “The Misadventures of Awkward Black Girl,” which ushered Rae into the Hollywood limelight. The creator celebrated with a YouTube livestream viewed by 30,000, as she and the cast relived the days when Rae was making art on a microbudget funded by fans on Kickstarter.

Now she is in production on the final season of “Insecure,” trying to soak up all the moments she can while maintaining a handle on her growing business portfolio outside the HBO series, with multiple productions in progress.

“I always knew I was going to do these five seasons,” Rae says. “Now that it’s coming to an end, and we’re shooting, I have no regrets. But there’s an element of knowing I’m going to miss this, and I don’t want to take this for granted. There’s no feeling like doing your first TV show and doing it with people who are also fresh with you, and growing and building with them.”

Closing the book on “Insecure,” along with celebrating the anniversary of the project that launched her Hollywood career, has been a somewhat strange yet emotional experience.

“In some ways, I’m saying RIP to that old version of myself and simultaneously, while terrified, excited about what the next chapter looks like,” she says.

That next chapter is marked by a new deal.

Rae has reupped her commitment inking an overall deal with WarnerMedia that’s valued at $40 million over five years and expands her reach across the company’s properties. The partnership gives HBO, HBO Max and Warner Bros. television exclusive rights to Rae’s work in television, plus a first-look film deal that spans WarnerMedia brands, including Warner Bros. Pictures Group, New Line and HBO Max. Rae and WarnerMedia declined to comment on the value of the deal.

“They wifed me up,” Rae quips, explaining why she signed on for five more years of matrimony after spending essentially her entire career with HBO.

It’s not as if Rae didn’t have other suitors. As her profile has grown, so have her opportunities. The Emmy-and Golden Globe-nominated TV actor made her feature film debut in 2018’s “The Hate U Give,” followed by starring roles in “Little,” opposite Regina Hall and Marsai Martin, and the romantic drama “The Photograph,” with LaKeith Stanfield. Her latest film, “The Lovebirds,” co-starring Kumail Nanjiani, had its original release plans derailed by the pandemic, and ultimately debuted on Netflix. She currently has projects in development at Netflix, Lionsgate, Sony and Universal.

But Rae’s heart and loyalty lie with HBO. “I have so much respect for the executives in various departments,” she says, explaining why she didn’t look to move elsewhere. “When people believe in you and build with you, I tend to want to further that relationship. That’s just been a staple of mine with so many of the people that I work with, on various projects. So I’m looking forward to seeing what this marriage looks like.”

HBO executives Casey Bloys and Amy Gravitt have been on the ride with Rae since the beginning. Bloys, now HBO and HBO Max chief content officer, discovered “Awkward Black Girl,” and the trio began developing the show to series in 2013. Bloys describes Rae as “unflappable” throughout the three-year process.

“She’s obviously very talented, and she’s very prolific,” Bloys says of why the network made it a priority to continue in the Issa Rae business. “It’s both her talent and the people that she finds and identifies that you know you can take a shot on. It’s been very good to work with Issa personally but also as a company, because she’s seeded a lot of talent elsewhere.”

Gravitt, who is executive vice president of HBO programming, says she most admires how Rae is constantly thinking about setting the stage for the next generation — “from the very beginning, while she was cracking her pilot [for ‘Insecure’] and bringing it to series. It was always about who else could she give an opportunity to, even though she was just at the very beginning of her career.

“I always say, it’s so funny seeing her on the cover of magazines and doing photo shoots. It’s like seeing our friend on the cover.”

Part of what makes Rae who she is, is where she’s from. She reps her hometown of South L.A. just about as hard as her idol Spike Lee reps his native Brooklyn, or the way LeBron James shouts out Akron, Ohio. The city is part of the fabric of her storytelling, proudly displayed on “Insecure.”

“I just feel like there’s an opportunity for South L.A. to really be our hub, in the same way that Koreatown is allowed to be Koreatown,” she says. “Why can’t Leimert or the Crenshaw District be considered our area? Why can’t we have the same Black-owned businesses and people owning the buildings and renting to each other? It takes trust, and it takes not being constantly denied resources, and it takes combating literally a system. Black people deserve that, and I want to be a part of building that.”

Rae still lives in the neighborhood and established the home base of Hoorae, her recently rebranded media label, inside a two-story structure in Inglewood. She’s also part owner of Hilltop Coffee + Kitchen, a coffee-shop chain with three L.A. locations including Inglewood, as well as Sienna Naturals, a hair-care brand that can be found at Target and Nordstrom.

Just as much as Rae wants to have her own studio, like Tyler Perry, or create and produce her first movie, she says, “I want to be able to expand my footprint outside of the industry; I want to make an impact, to combat gentrification, to help combat homelessness in the city.

“When I’m driving to work on Crenshaw seeing a Black woman use the bathroom on the sidewalk because she doesn’t have a home, and she’s not being cared for, and people just drive by — we can get used to stuff like this, and I want to do my part because I don’t want to get used to it.”

Rae also uses her clout to support projects like Destination Crenshaw, an infrastructure and economic development project celebrating Black art and culture on that very street.

“When I think about my future and my personal goals, I focus on how I leverage what I’m doing currently to shine a light and make some real change,” she says. “I’m not going to change the world, but I know that if it’s in my neighborhood, if it’s in my community, then I can at least figure out how to help us do better here.”

Rae aims to make waves just as large in the industry, from her little corner of the universe and with her loyal team at Hoorae (pronounced “hooray”). From her producing partners to her professional team (managers, agents, publicist), most of the people surrounding her have been there since the digital days, leveling up comparably as she’s made her own moves.

Rae considers her collaborators integral to her success, explaining that she’s built up her confidence “by working with people who I trust, who I trust to be honest, whose opinions I trust, and by fostering in my own work environment a culture of transparency and honesty. You can’t be scared to talk to me. You can’t be scared to give me feedback. You can’t be scared to be like, ‘This sucks, and it’s not for me.’ My biggest fear is to be surrounded by yes people, because I’ve seen that in effect.”

Team Issa begins with the “core four”: Benoni Tagoe, president of the audio content company Raedio; Rae’s publicist Vanessa Anderson; Deniese Davis, co-founder of management label ColorCreative; and Rae — all of whom have been working together since “Awkward Black Girl” debuted in 2011. From there, the team has multiplied to the 23 employees within Hoorae.

The company is Rae’s next step toward world domination — or at least to becoming a media mogul.

The name is a play on Rae’s, but both her stage surname (her given name is Jo-Issa Rae Diop) and the “Hoorae” pun come from the creator’s late aunt, Rae Louise Hayward. Hayward was a Bay Area artist who co-founded a collective for underrepresented artists called The Art of Living Black, and used “HaRae for the Arts” as part of her brand. Rae says the new name represents “a fresh start” and makes her efforts in Hollywood feel more official.

“Issa Rae Prods. [the company’s previous moniker] felt too limiting. It feels like just me. And in name, I want to do more than just me,” she explains. “I think the rebrand just feels like ‘We’re here. This is what we’re about to do moving forward. And this is who we are.’”

The relaunched company consolidates the film and TV development division (led by Montrel McKay and Sara Rastogi), her Raedio audio content company (led by Tagoe) and the digital brands (led by Rich Stevenson) under one umbrella. Rae’s other venture, ColorCreative (which she founded with Davis in 2014 as a pipeline for underrepresented writers) is a sister company to Hoorae and now is led by former CAA exec Talitha Watkins.

It’s been a busy year for the team, which has multiple productions in various stages of progress. The HBO Max comedy “Rap Sh*t” is in pre-production, having launched its virtual writers’ room in late February, shortly after the “Insecure” writers put the finishing touches on their final episodes. Meanwhile, the Hoorae team is reviewing edits on the HBO documentary series “Seen & Heard,” which explores the history of Black television. And those are just the projects they can talk about.

Hoorae takes a 360-degree approach to production, similar to the way Rae and her team functioned before the days of WarnerMedia deals. The best example of the company’s synergy lies in “Rap Sh*t,” which is co-executive produced by Yung Miami and JT of hip-hop duo City Girls. Rae created the series and executive produces alongside McKay and Rastogi, while Raedio handles music supervision for the show, and the Hoorae digital team creates online-first content around it.

With the WarnerMedia deal, the ultimate goal is to be as prolific for their new partners as Warner producers J.J. Abrams or Greg Berlanti, McKay says.

“We see what they’re doing, and we’re inspired by it and want to be in the same league,” he explains, also pointing to the success of Shonda Rhimes and Shondaland’s “Bridgerton” for Netflix as a model to follow. “‘Insecure’ is something that’s going to live forever as a cultural touchstone. Anything else we touch, we just really want to make sure audiences love and engage with it. Issa doesn’t put her name on anything unless she’s going to do the work to justify her name being there.”

Case in point: One of Rae’s protégés, Syreeta Singleton, will serve as showrunner and executive producer of “Rap Sh*t.” Singleton got her start as a writer’s assistant on “Insecure” in 2017 and is also an alum of ColorCreative, which now manages her career. Singleton (who is represented by Rae’s attorney John Meigs) also wrote the script for the “Set It Off ” remake that Hoorae is producing.

Rae “finds the greatest pride in watching others succeed, especially Black women,” says Robin Thede, who appears on-screen with her on “Insecure” and works with her behind the scenes on “A Black Lady Sketch Show.”

After Thede’s late-night series “The Rundown” was canceled, Rae called her old friend and asked if she wanted to work on something together. Rae then convinced Thede to bring the “Black Lady Sketch Show” concept to HBO, and it was ordered straight to series. The series earned three Emmy nods for its first season, and Season 2 is set to premiere April 23.

“I think that’s the magic of Issa. I don’t know if there’s a whole bunch of people that would have jumped Syreeta to showrunner [of “Rap Sh*t”], but she is ready and she’s gonna crush it. And it takes people like Issa to say, ‘Yeah, you’ve got next,’” Thede says. “If you’re out at an event or a party with Issa, she’s gassing you up, not in an annoying hype kind of way, but she’s somebody who your dreams are safe with. And not only will she say, ‘I support that dream.’ She’ll say, ‘How can I help you?’”

The success of “A Black Lady Sketch Show” has been an important proof of concept for the Hoorae model of development and production and its future at HBO. Thede says it’s no coincidence that Michaela Coel’s “I May Destroy You” and Misha Green’s “Lovecraft Country” are also on the network. “Insecure” opened the door.

“HBO, if people haven’t noticed, is Black woman central,” says Thede, who has an overall deal with Warner Bros. TV. “I don’t think there’s any other place on television where Black women are telling their stories in such a high quality. And that’s no shade to anyone else. That’s not an accident; that’s being curated.”

Will Packer — who first worked with Rae when she starred in his 2019 film “Little” and reunited with her for last year’s “The Photograph” — says he was immediately impressed by her mind for producing, though she was only appearing on camera for the project. That ability to see the bigger picture is a rare quality in actors, he explains, but rarer still is Rae’s “lack of pretense,” which Packer believes is her secret weapon. “In today’s oversaturated content market, you’ve got to be able to connect organically with audiences, and that’s what she does,” he says. “Part of the reason she does that is because she’s not trying to. Issa’s just going to be Issa. What you see is what you get, but she does it with an eye towards real people, especially Black women but not exclusively Black women.

“There’s so much content out there now that audiences are so much more discerning. It’s a great time for content creators and platforms and all that, but everybody’s not gonna survive, everybody’s not going to make it, every platform’s not going to be here in five years. But those folks who have those real, authentic connections with audiences will still be around.”

Staying power is precisely what Rae has been working toward. When she thinks about what’s next for her and her company, she dreams big, with aspirations to be like Spike Lee or Debbie Allen. But on a more macro scale, Rae’s focus is on creating a permanent space for Black people in entertainment.

“It’s about rooting our place within this industry, establishing longevity, building the platforms, because I’ve seen it all disappear,” she explains. “I’ve seen us be hot. I’ve seen us be a trend for years, and it’s frustrating to know what we’re capable of but then constantly see it be ripped from under us because we don’t have the control.

“Someone like Tyler Perry is definitely a role model. To see what he’s done in such a short amount of time — what he’s built and what he’s trying to build actively — is amazing to me. I think more of us need to do that, and we’re inspired because he can and he did.”

With her new setup at WarnerMedia, Rae moves a little closer to Perry’s level of control.

“What feels different about this time is that it feels more up to me about what to do. It’s in my hands, and in some ways, that’s what makes it the most scary,” she says. “There’s always going to be gatekeepers, but it feels like the gate is a bit more open, and I get to decide where to go on my own.”

Not to mention the money factor, which ups the ante even further.

“I just wrote an email today turning down money. I never thought I’d be in a position to turn down anything, like, ‘Oh, this doesn’t really fit; this doesn’t really align,’” Rae laughs. “I’m like, ‘Who is this?’ because the person who couldn’t afford a cup of coffee, being broke before doing the Kickstarter campaign, would be like, ‘Who the fuck do you think you are?’”

The Kickstarter campaign Rae references is one of the legendary tales of her early rise to stardom. Fans raised $56,000 via the crowdfunding site to help Rae finish production on the first season of “Awkward Black Girl.”

“But I’ve become a bit more confident in who I am, the decisions that I want to make and the place that I want to have in this industry,” she continues. “Do I feel supremely confident that I’m going to get there? I have my moments of doubt, but I’m so focused and I’m so intentional, and I think that that stems from the early days of shooting ‘Insecure,’ feeling like ‘OK, I got the momentum. I have to keep it going. I’m gonna secure my place; I’m gonna secure this show as a staple of something — whether it’s a staple of now or the future.’ But obviously, I could not have imagined where it would take me.”

It’s that hustle that has always gotten Rae through. In fact, the person who probably had the strongest belief that she would end up in this position was Rae herself — the 11-year-old version. She says the young girl who visited the set of “Moesha” and was inspired to submit her own script to producers always believed that she would make it, despite the discouraging rejection letters.

“If she saw me right now, she’d be like, ‘About time,’” Rae laughs. “She’d be horrified that it took so long.”

Styling: Jason Rembert; Makeup: Joanna Simkin/The Wall Group; Hair: Felicia Leatherwood; Manicure: Eri Ishizu/Opus Beauty; Look 1 (lead photo): Dress: Oscar de la Renta; Belt: Valentino; Earrings: Khiry; Shoes: Christian Louboutin; Look 2 (1st and 2nd photos after the cover): Top & Pant: Alexander Vauthier; Earrings: Chanel; Ring: Boucheron; Shoes: Gianvito Rossi; Look 3 (cover and last photo): Coat: Coach; Top: Valentino; Jewelry: Boucheron; Shoes: Christian Louboutin

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