Issa Rae Is Creating A TV Empire With A Powerful Purpose

By Kimberly Drew | November 17, 2021

As we collectively enter the next phase of the ongoing pandemic, many find themselves searching for a sense of purpose. The return to “normal” has brought the promise of freedom and life beyond this pandemic, but with the realities of the variants, increasing voter suppression and the disenfranchisement of already marginalized communities, feelings of optimism are waning. Even the most secure professionals find themselves asking: What is my work? What is my place? This, and the recent amnesia since last year’s uprisings, incites a feeling of whiplash for many Black creators. Is there still an appetite for our needs, for our creativity, and our stories?


Photographed by JD Barnes Styled by Jason Rembert
Photographed by JD Barnes Styled by Jason Rembert

Enter Issa Rae, our ever-busy cover star. On the eve of our conversation, Rae is locked into production mode in Miami on her next project, Rap Sh*t, a comedy that is loosely based on the internet and pop culture phenoms JT and Yung Miami of the City Girls.

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Photographed by JD Barnes Styled by Jason Rembert. Balenciaga top and skirt, BALENCIAGA.COM; Nadri stud earrings, NADRI.COM; Christian Louboutin Heels, CHRISTIANLOUBOUTIN.COM.

Our call has been bumped several times in pursuit of a free hour in her schedule to chat. “I am trying to figure out how to make it work and to still be productive and to still be able to have ‘me’ time,” she tells me by phone during what would otherwise be a lunch break. “By the time I get home, I’m exhausted and I don’t want to do anything, but I have to.”


Louis Vuitton coat, louisvuitton.com; earrings, stylist’s own; Jessica Rich heels, jessicarich.com. Photographed by JD Barnes Styled by Jason Rembert
Louis Vuitton coat, louisvuitton.com; earrings, stylist’s own; Jessica Rich heels, jessicarich.com. Photographed by JD Barnes Styled by Jason Rembert

In this moment of fogginess, Rae pushes through the noise and spends every moment of her day creating space within the industry for new stories to be told. Since the 2011 debut web series The Misadventures of Awkward Black Girl, she has kept a razor-sharp focus on the future. This year alone, Rae has just completed the fifth and final season of the critically acclaimed Insecure, premiered The Sweet Life (which has been renewed for a second season), a Baldwin Hills-inspired series, and is working on a whole host of other films, series, and projects, including a reboot of Project Greenlight, the Matt Damon-Ben Affleck reality show that was created to support aspiring filmmakers.


Alexander McQueen coat and dress, alexandermcqueen.com; Alexis Bittar earrings, alexisbittar.com; Alexandre Birman heels, alexandrebirman.com. Photographed by JD Barnes Styled by Jason Rembert
Alexander McQueen coat and dress, alexandermcqueen.com; Alexis Bittar earrings, alexisbittar.com; Alexandre Birman heels, alexandrebirman.com. Photographed by JD Barnes Styled by Jason Rembert

“I am trying to figure out how to make it work and to still be productive and to still be able to have ‘me’ time.”


Photographed by JD Barnes Styled by Jason Rembert
Photographed by JD Barnes Styled by Jason Rembert

Rap Sh*t was recently ordered as an eight-episode series order at HBO Max and is being produced under her Hoorae production banner— inspired by Rae’s late aunt, Rae Louise Hayward, an artist and organizer in the Bay Area. Hayward co-founded a collective for underrepresented artists called The Art of Living Black, and used “HaRae for the Arts” as part of her brand. “My aunt was my gateway into the medium of art. She was very passionate about letting her nieces and nephews learn about artists like Jacob Lawrence. She saw a lack of representation in terms of Black artists being able to showcase their work in the Bay Area, and I resonate with that so much in the entertainment industry.”


Photographed by JD Barnes Styled by Jason Rembert
Photographed by JD Barnes Styled by Jason Rembert

Working alongside her longtime collaborator, director Melina Matsoukas, has aided her in realizing these lessons from her aunt. “To have Melina kind of reintroduce me to this world and to be able to [work with and] showcase this new generation of artists is really important.” Fans of Insecure will note a major key change in the visuals of the show with Season 3. On screen we see the band of 20-somethings grow up, break up and begin their own families. In its most recent season, it was clear to Rae and her team that they wanted characters on the show to be able to establish their own tastes and represent their growth on screen. “We had Issa move into her new space and, as such, we thought that we wanted her to have a more adult apartment.”

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Photographed by JD Barnes Styled by Jason Rembert

In one of the opening scenes of Season 4, Issa Dee says, “Ever since I got my place set up, it’s like opening up to a whole new world.” On the walls of the apartment, we see artworks by the emerging artist Nakeya Brown, a California native, who makes captivating images that show care rituals performed by Black women in domestic settings. And, in another scene, the work of February James is perfectly placed in Molly’s kitchen. For Rae, it isn’t enough to simply signal her commitment to Black creators but to push them into action. Despite her packed schedule, Rae remains ever-curious of emerging talents. For example, while working on a talk show, she connected with Adrienne Wade, who had been working as a sound mixer. After their time together on set, Rae learned that Wade was a prolific artist and added two of her abstract murals to her personal collection. “There’s something where I get to interpret it for myself but also clearly understand what she was feeling at the moment. Art should feel like it’s a piece of you, it’s yours.”


Photographed by JD Barnes Styled by Jason Rembert
Photographed by JD Barnes Styled by Jason Rembert

In both Sweet Life and Insecure, we see Rae’s deep love for South L.A. and specifically, Black Los Angeles radiate across the screen. On Sweet Life, Amanda Scott, a burgeoning businesswoman, claims that she wants to “Buy Black the block,” and in the fictional world of Insecure, Issa Dee launches her own block party to support real-life businesses in the area.


Photographed by JD Barnes Styled by Jason Rembert
Photographed by JD Barnes Styled by Jason Rembert

“Los Angeles can stand among the best cities like Detroit and Harlem when it comes to being a breeding ground for some of the greatest artists of our time.”


Dries Van Noten dress and blazer, driesvannoten.com; Third Crown earrings, thirdcrown.com; Gianvito Rossi heels, gianvitorossi.com. Photographed by JD Barnes Styled by Jason Rembert
Dries Van Noten dress and blazer, driesvannoten.com; Third Crown earrings, thirdcrown.com; Gianvito Rossi heels, gianvitorossi.com. Photographed by JD Barnes Styled by Jason Rembert

Many wonder how to contribute to conversations (both real-life and scripted) about building Black wealth without crossing the picket line to add to awful gentrification in traditionally Black neighborhoods. “I think Black wealth is important if it’s being redistributed in our community,” Rae tells me. “So Black wealth excites me when we can make ourselves the priorities and our communities the priority. That’s the only advantage.” For Rae, this has meant investing in projects like Destination Crenshaw, designed to support local business and creative projects in the Crenshaw District.


Photographed by JD Barnes Styled by Jason Rembert
Photographed by JD Barnes Styled by Jason Rembert

On and off-screen, Rae remains committed to telling luscious and full stories of her beloved L.A. Rae hopes to show that “Los Angeles can stand among the best cultural cities like Detroit and Harlem when it comes to being a breeding ground for some of the greatest artists of our time. I think L.A. gets a bad rep for being vapid and superficial and Hollywood. And to me, it is about highlighting the real people who are here and about highlighting the culture that exists here.”


Gucci top and skirt, gucci.com; Khiry earrings and ring, khiry.com; Alexandre Birman heels, alexandrebirman.com. Styling: Jason Rembert Hair: LaRae Burress of Texture Management Inc Makeup: Joanna Simkin at The Wall Group Manicure: Yoko Sakakura at A-Frame Agency using OPI Set Design: Sam Jaspersohn at See Management Gaffer: Jason Beck Location: 10102 Angelo View Drive, Beverly Hills, Calif., designed by Disco Volante, listed with The Beverly Hills Estates Photographed by JD Barnes Styled by Jason Rembert
Gucci top and skirt, gucci.com; Khiry earrings and ring, khiry.com; Alexandre Birman heels, alexandrebirman.com. Styling: Jason Rembert Hair: LaRae Burress of Texture Management Inc Makeup: Joanna Simkin at The Wall Group Manicure: Yoko Sakakura at A-Frame Agency using OPI Set Design: Sam Jaspersohn at See Management Gaffer: Jason Beck Location: 10102 Angelo View Drive, Beverly Hills, Calif., designed by Disco Volante, listed with The Beverly Hills Estates Photographed by JD Barnes Styled by Jason Rembert

In a time marked by insecurity, Rae is a beacon for resisting peril. In a viral post to her Instagram stories, she brilliantly quips, “It’s feeling like me season.” If this is the case, I hope we can all get season tickets.

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Photography by: JD Barnes. Balenciaga top and skirt, balenciaga.com; Nadri stud earrings, nadri.com; Christian Louboutin heels, christianlouboutin.com. (Lead Image)