ISSA RAE'S NEXT CHAPTER:
The Mogul Era
Six months after fans said farewell to “Insecure,” the writer, producer and actor opened up for TODAY’s first-ever digital cover story about her new project, “Rap Sh!t,” keeping her personal life private and what we can expect from her “mogul era.”
By Sylvia Obell
Photography by Raven B. Varona
It’s a hot June day in Southern California’s Venice Beach, and Issa Rae is back in front of the camera like she never left. We’re on a rooftop overlooking the beach, and the only thing brighter than her flowy yellow dress is the sun kissing her skin. The leader of the “Awkward Black Girl” movement is quiet on set, but once photographer Raven B. Varona begins to shoot, it’s clear the literal CoverGirl has learned a thing or two about finding her angles over the years. The only time I remember that she’s not actually on "America’s Next Top Model" is when she exclaims, “Ah, I forgot to take off my Fitbit!” after each outfit change.
To help channel her boss energy on set, Rae has requested a playlist full of popular female rap artists like the City Girls, Megan Thee Stallion and Latto. When a line from the latter’s song “Big Energy” starts blaring through the speakers — “Bad b—-, I can be your fantasy” — Rae lip-syncs along looking like a dream herself — or more accurately, a dream realized.
Rae’s first chapter in Hollywood is the stuff of lore. She came bursting into our living rooms in 2016 as the creator, writer and star of the HBO comedy “Insecure.” An instant hit, the series went on to become a defining television show for a generation of Black viewers thirsty for representation. And fans didn’t just watch episodes; they live-tweeted and debated topics from sexual fluidity and outgrowing friendships to open marriages and the “break baby” Issa’s love interest Lawrence had during their breakup. They also learned the songs from the soundtracks, bought the outfits, tried the hairstyles and Instagrammed themselves at all of the South Los Angeles locations from their favorite episodes. By the end of the second season, Rae had become one of the most sought-after celebrities in the industry, and “Insecure” was more than a show — it was culture.
When we meet six months after the series’ finale has aired — and recently earned its 12th, 13th and 14th Emmy nominations — it’s clear that Rae is looking forward, not backward. After a busy morning of shooting three looks for TODAY’s first-ever cover story, Rae changes back into cozy sweats to chat with me in her dressing room over lunch. But before diving into the “What’s next?” question that’s been lingering on all of our minds, I first ask Rae what she’s most proud of.
“When people are like, ‘I started on “Insecure”’ — that’s so special, whether they're writers, costume designers, cinematographers or directors,” Rae says. “Being able to let people hone their skills on ‘Insecure,’ and then watch them show and prove to the point where they're now demanded by other projects … that’s dope to me, because I saw that happen on Black TV shows growing up.”
She adds: “You start to build a foundation: a group of people that you've come up with, and we are the ones giving each other our second chances, and our third jobs, and then our fourth jobs. And they, in turn, are doing the same thing with their extended group of people. I think it’s a mentality that'll lead to another shift of us looking out for each other.”
Very few have shown the power of networking across the way Rae has — meaning, working with the people around you, not above. In an industry where everyone’s vying to get the same big — and, often, white — names to star in, direct or write for their projects, Rae has proven that you don’t need a cast of preapproved Hollywood A-list names to push a product. In fact, she managed to build her own table instead of begging for a seat at someone else’s.
Take Yvonne Orji, for example. In 2015, for the role of “Insecure” main character Issa Dee’s best friend, Molly, Rae cast Orji, then an aspiring comedian with no real acting experience. “Issa changed my life — she gave me an opportunity!” Orji says. “She has an inspiring ability to see new talent and give the underdogs a chance.”
Since making her small screen debut on “Insecure,” Orji has appeared in projects like “Jane the Virgin,” and the film “Vacation Friends,” and headlined two comedy specials. Orji points out that, similarly, the showrunner of “Rap Sh!t,” Syreeta Singleton, was a writing assistant on “Insecure” just five years ago.
“Issa provides opportunities and space to thrive, whereas the old gatekeepers of Hollywood make us jump through hoops, and then determine we are still not ready.”
“Issa provides opportunities and space to thrive, whereas the old gatekeepers of Hollywood make us jump through hoops, and then determine we are still not ready. She’s kind of like the new gatekeeper, but in a way that she actually does the work and opens the gate for multiple people to come through. She cultivates talent in a way that’s just beautiful.”
Sarunas J. Jackson, the actor who played Molly’s love interest Dro, echoes Orji’s sentiment. “It is such an honor to be a small part of Issa’s journey, and to see her dropkick down doors in this business” he says. Post “Insecure,” Jackson went on to appear in Hulu’s “Good Trouble” and HBO Max’s “Made for Love,” as well as the recent horror-comedy film “Gatlopp.”
“To see more and more Black women get opportunities to create, lead and produce — and to know that Issa is one of the reasons for that shift — is so beautiful,” Jackson says. “She’s already a legend in my eyes, and this is only the beginning.”
“To see more and more Black women get opportunities to create, lead and produce — and to know that Issa is one of the reasons for that shift — is so beautiful.”
The thing about building your own table, though? It’s exhausting, and the burnout that can come with it is something Rae knows well. Over the course of 2021, the now 37-year-old found herself finishing the last season of “Insecure,” executive producing the first season of the upcoming HBO Max series “Rap Sh!t,” filming an episode of Apple TV’s anthology series “Roar,” and running her growing media production company, HOORAE — all while planning a wedding with her longtime partner, Louis Diame, that she somehow managed to keep secret from the world until she shared the stunning photos on Instagram.
“Last year taught me that the balance needs to be planned in advance for me, because, otherwise, I would just work, work, work, work, work,” Rae said. “Even after ‘Insecure,’ like a dummy, I did an episode of ‘Roar.’ Then I flew to France, and I was like, ‘Why did I need to do that? I could have taken that two weeks in between to chill and prepare and do all these things?’ But I chose to do this episode. It was a great experience … but I know myself. I know how frustrated and/or tired I can get in some cases, and I’m not doing my best when I’m like that.”
Rae says she’s learned that actively planning time off and committing to it out loud so everyone on her team can hear it is vital to her self-care. “Because people will try you,” she says. “They'll be like, ‘Oh, this is coming up, are you sure? There’s this much money here, are you sure?’"
I was relieved to hear that Rae didn’t waste much time implementing that lesson: She started 2022 with some much-needed rest. “After the finale aired, I got on a plane. I did all the stuff that I didn't get a chance to do, like a honeymoon. I took all of January off and traveled and finally got a chance to just chill and think,” she says.
In true Capricorn style, Rae admits that while the time off was great for her spirit, starting a new year without working was hard for her.
“There’s an expectation people have that you need to keep up with their lives on social media, and it's like, ‘No, you’ve got to talk to me.”
A break that wasn’t as difficult? Posting on social media. “There's an expectation people have that you need to keep up with their lives on social media, and it's like, ‘No, you’ve got to talk to me,’” she says. If you look at Rae’s Instagram today, you’ll notice it’s been scrubbed of most of her older posts, and as she slowly but surely begins to post more, she expects she’ll continue to use social media as more of a marketing tool rather than as a window into her real life.
She did, however, confess to having a finsta (“fake” Instagram) that she uses to explore one of her favorite topics.
“I'm a big food person! So I have a finsta dedicated to food. It’s like, not fire at all. I don't follow anybody except for other food pages, and that's like my happy place,” she says, her eyes drifting off as though she’s picturing her favorite meals as we speak.
If you are looking for candid Issa Rae moments on social media, your best bet is her Instagram story or her occasional tweet. Case in point: In March, she tweeted a since-deleted message to shut down pregnancy rumors. Now, she laughs at the memory, saying she felt she had to do it because her own mother started questioning if the speculation was true.
“My sister sent me a screenshot of my mom texting her an article like, ‘Did she tell you ... Are the rumors true?’ I was like, ‘What?!’ (My sister) was like, ‘Not Mom believing in gossip!’ I was like, ‘But she texted you and she didn't even ask me!’ I'm like, ‘Mom, a pregnancy … you really think that I would hide a grandchild from you? That you’ve been begging for?!’ So I had to say something, because it was getting out of hand.”
While Rae’s mom will always be in the loop on personal matters, we, the public, are another story. That became apparent in July 2021 when Rae posted photos with her partner, Diame, for the first time on social media — from their wedding. Until that point, she had never even confirmed being in a relationship. The internet was so shook that “I’m on my Issa” became synonymous with keeping your relationship offline until marriage.
Rae lets out her signature laugh when I inform her she’s become a verb in this way. She says that she’s always been naturally private. I ask her if she’ll keep this same energy if she ever decides to expand her family. “I’m not sure,” she says. “Maybe if I have a child, I'll feel like, ‘Everybody needs to see this thing!’ I don't know!”
What we do know for sure is that Rae’s next career chapter is stacked with exciting projects, starting with the premiere of “Rap Sh!t” on July 21. Set in Miami, the 30-minute (no, you’re still not getting a full hour from Rae, folks!) HBO Max comedy series follows estranged friends Shawna (Aida Osman) and Mia (KaMillion) as they try to make it as a rap duo. The idea came from an early draft of “Insecure” that explored main character Issa Dee’s desire to become a rapper; Rae eventually nixed the idea because she wanted the show to feel more grounded. But when HBO asked her what she wanted to do next, she felt it was the perfect time to delve into a world that’s long fascinated her.
“Thinking about this time in music, it just feels different,” Rae says. “There's so many women rappers who are killing it. There are beefs here and there, but for the most part they all seem to be having a good time. They support each other, and that world felt interesting to me. So I just started thinking about the music industry and what the come up would look like, and the come up specifically through the lens of the internet.”
Exploring the intersection of internet and stardom felt very real to Rae because that’s how she, like many of us, first came to know some of her current favorite rappers, like Megan Thee Stallion and Cardi B. It’s also the way many of us came to know Rae herself, through her hit web series “Awkward Black Girl,” which debuted on YouTube in 2011. The fact that she’s now in a place to create a TV series on premium cable that explores that very kind of internet-y dynamic is both timely and meta; it’s also what makes Rae one of the clearest voices of the millennial generation.
When I ask her if she’s worried about a sophomore slump, Rae says she’s happy just to be behind the scenes this time around. “I think the pressure feels less to me because I'm not in it,” she says. “There's obviously still pressure, but the cast killed it, and I really do believe that it's such a fun summertime show … I really just hope people like it and f— with it and embrace it, and just have a good time watching it.”
For those who are fans of Rae’s work in front of the camera, fear not. She has several movies on the way, including “Vengeance,” the directorial debut from actor/writer/comedian B.J. Novak, out July 29. And while she can’t give too many specifics, she’s also got a role in Greta Gerwig’s highly anticipated “Barbie” movie, which is currently filming. Rae says it was Gerwig’s specific vision for the film that sold her. “I was like, ‘This sounds crazy, but OK. Let me just read the script.’ When you read the script, you're like, ‘Oh, I get it!’ It’s very funny, and it’s just very specific to her … working with her was absolutely amazing.”
When I ask Rae if she has any aspirations to write a movie screenplay of her own, I’m delighted to learn she’s already gotten started. “It's part of the next chapter. I’m looking to film one soon,” she says, while also confirming she’ll attempt to pull double duty by acting in at least one of her screenplays. “I’ll see how that goes!” she says with a weary laugh.
As the multi hyphens attached to Rae’s name continue to grow, so will her media empire. At this point, she has built multiple tables that all fit under the umbrella of HOORAE. In addition to the film, TV and digital projects HOORAE produces (like the Emmy-winning “A Black Lady Sketch Show” and the HBO Max reality show “Sweet Life”), there’s also Raedio, an “audio everywhere company” that does everything from music supervision and publishing to podcasts and events, and ColorCreative, which serves as a management company for diverse creatives.
Balancing being the boss of a fast-growing entertainment company while also being a writer and creative is not easy, and it’s a dance Rae admits she hasn’t quite mastered yet. “I'm struggling,” she says. “I was just complaining about that at my breakfast with (“Insecure” showrunner) Prentice (Penny). It's hard to do both well, and I really want to be good at both. I don't think I'm there yet, and I won’t be until I figure out how that balance works out … that's something that I'm actively working on.”
“I 100% want to do more outside of the traditional industry. But I want to kill it in this industry first.”
In the meantime, Rae will continue following her vision, no matter how much juggling it takes. One of her next moves? Focusing on impacting the communities around her. She’s already dipped a toe in with Hilltop, a coffee shop she co-founded in L.A.’s Inglewood neighborhood with two small-business owners. The HBO documentary “Insecure: The End” chronicled the final season of the series, and at one point highlighted Rae’s efforts to employ South L.A. natives as security personnel, shuttle drivers and more while “Insecure” was filming. And she plans to expand that work. “That’s something I’m actively developing,” she says. “I 100% want to do more outside of the traditional industry. But I want to kill it in this industry first.”
It seems as though the universe is conspiring to give Rae, a true alchemist, everything she wants to continue making her visions a reality. “I want to truly enter my mogul era, and that comes from empowering and building other moguls of color,” Rae says. “I think that's my aspiration, and I just want to do it well. I want people and this industry in particular to take us seriously. I want to be a competitor with the best.”
Photographer: Raven B. Varona
Photo Assistant: Jesse Belvins
Digital Tech: Kyle Makrauer
Stylist: Jason Rembert
Styling Assistant: Shameelah Hicks
Hair: LaRae Burress
Makeup: Joanna Simkin at The Wall Group
Manicurist: Yoko Sakakura
Head of TODAY Digital: Ashley Codianni
Editorial Director: Arianna Davis
Art Director: Kara Haupt
Photo Editor: Tyler Essary
Talent Booker: Christina Manna
Videographer: Laura Spotteck
Video Editor: John Paulsen
Social: Bianca Clendenin, Peyton Young
Look 1:
Dress: Oscar de la Renta
Earrings: Misho Designs
Shoe: Rebecca Allen
Look 2:
Dress: Dundas
Shoes: Stuart Weitzman
Earrings: kit
Look 3:
Suit: Sergio Hudson
Shoes: Stuart Weitzman
Earrings: Cuyana