GREATEST / Issa Rae

From Awkward Black Girl to Insecure, the Los Angeles auteur is shifting paradigms through entertainment, collaboration and entrepreneurial activism.

INTERVIEWER: MELODY EHSANI PHOTOGRAPHER: JOSHUA KISSI STYLING: JASON REMBERT MAKEUP ARTIST: JOANNA SIMKIN HAIR ARTIST: FELICIA LEATHERWOOD HAIR ASSISTANT: LARAE BURRESS SET DESIGN: M RASMUSSEN MOVEMENT DIRECTOR: NANA YAA ASARE BOADU
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Issa Rae is easing herself back into daily life after more than a year of lockdown. From the amount of projects she’s working on at any given moment, you’d never know it.

Just this year, Rae—the creator, star, writer and producer of HBO’s Insecure—wrapped the fifth and final season of her hit show before beginning production on Rap Sh*t, a new HBO Max project set in Miami.

And despite the restrictions of the pandemic, Rae’s creative energy never showed any signs of slowing down. If anything, the time spent in near isolation only sharpened her resolve, manifesting itself across entertainment projects, a music label and a collaboration with Converse. All of this while fostering community-driven work throughout historically Black Los Angeles neighborhoods, as both a partner in Inglewood’s Hilltop Coffee and a supporter of the expansive open-air museum Destination Crenshaw.

Finding a moment of calm amidst her whirlwind schedule, designer Melody Ehsani caught up with the prolific auteur to discuss Black beauty, resisting gentrification and turning failure into victory.

Dress: Maison Margiela Tape-Print Silk Dress; Breastplate: Comme des Garçons Hommes Plus Spiked Harness   

With Insecure, you revolutionized TV from the perspective of a young Black woman. What social progress have you seen in the industry since the show’s debut?

I can't take all the credit for our show. A lot of us had the same idea around the same time: We wanted Black people to be beautiful. At the same time that Insecure premiered in Atlanta, I went to the Queen Sugar screening, and I was like, “Oh my God, it's beautiful.” Around that same time, Moonlight came out. I remember feeling, “This is a renaissance.”

Since then other shows and films have popped up, but we're not in this extreme renaissance of rich content that we all thought we'd be in. We're just scratching the surface.

Dress: Maison Margiela Tape-Print Silk Dress; Breastplate: Comme des Garçons Hommes Plus Spiked Harness; Footwear: Air Jordan 1 Retro High OG ‘Dark Mocha’ 2020   

As a designer, jewelry throughout time is so fascinating for me. Hundreds and hundreds of years ago, the Maasai and Native Americans were doing the same designs with the same colors and materials, but they didn't know about the other's existence.

It goes back to things being phases, even where fashion is concerned. To think that across the world across time and across different cultures that people are thinking the same thing at the same time—it's frightening and inspiring.

I think it’s inspiring because human beings are energy in motion, and when energy is released it's available for anybody to connect to. You connected to that energy and translated it through your LA lens.  I've never seen LA captured in a piece of art like that before in my life.

That's so beautifully put. It’s a privilege to work with collaborators like Melina [Matsoukas], who helped make that possible. I wanted to showcase LA, but I didn't know I wanted to showcase it like that, and then someone like her came along. She was the right one.

Outerwear: Junya Watanabe Sequin Coat; Jewelry: Boucheron   

Moving forward, what are you excited about? Do you feel being from LA is going to continue informing your work? 

Without a doubt. LA is so much a part of who I am, and I jump at the chance to represent it in any way, whether it's through my own work or supporting other people's work. There are a couple of projects that are LA-scented that I'm excited to explore.

Right now I'm at a writing camp for the next show I'm doing called Rap Sh*t, which is based in Miami. It’s super exciting to explore a city I love as a tourist.

Outerwear: Junya Watanabe Sequin Coat; Footwear: Church’s Shannon Studded Derby; Jewelry: Boucheron   

I love that. I also know you're involved in a lot of community organizations. What can you tell me about that? I know you work with Destination Crenshaw, and you shout out Hilltop Coffee + Kitchen a lot.

I love being involved in my neighborhood, Inglewood, and the neighborhoods nearby. I'm thinking of ways to uplift the people who live here and to support the people who live here during a time when we're being pushed out [due to gentrification]. I'm aligning myself with organizations, especially during the pandemic, to make sure that we have housing and jobs here.

I'm a part owner in Hilltop, and we make sure we hire people from the community. We also teach financial literacy and make sure we have the tools to build within our own communities. I have so much to learn and so much that I want to do. I often feel overwhelmed about where to start, but I start anyway.

Outerwear: Junya Watanabe Sequin Coat; Footwear: Church’s Shannon Studded Derby; Jewelry: Boucheron   

I love the financial literacy part. So many of us don't come from generational wealth, and once you start making money, what do you do with it?

And it's not taught in schools, or it wasn’t taught in my school. That's not something that you even think about learning, and it feels like everybody else knows about it. Even now I feel like I should know more than I do. It's daunting on purpose, to keep you out of the know, to keep you dependent.

I think that's part of a construct of white supremacy, truly.

Without a doubt.

Are the financial literacy courses held at Hilltop?

Yes. We do them for our own employees and for the community, too.

Dress: Chanel White Tweed Tunic Dress; Footwear: Off-White x Nike Air VaporMax ‘The Ten’ 2017; Jewelry: Piaget   

As somebody who is truly self-made, is there any advice that you have for the next generation of creatives? As a fly on the wall during Insecure, I saw how much you created an infrastructure of paying it forward in terms of who you hired; there were so many guest directors and shadowers. The show was almost a social and economic development program on the side. I feel like that has a lot to do with your vision.

Man, I can’t count the number of times that's been discouraged, believe it or not. I've heard the terminology, that it's just easier to get on, easier to sell your work or to pitch a project when it's “clean” of others. One of my most cherished friendships was destroyed because I bought into that. It doesn't have to be like that though and you can make space for others. You can fly with others if you want to.

Conversely, I’ve had to learn to stand on my own two feet, and recognize what I'm bringing to the table. It's important for creatives to understand what their own value is and to recognize the value in the people they collaborate with.

In creative spaces, the powers that be want you to be dependent on them and their resources. There is value for them, for you to be vulnerable to that, and that is not lost on me. 

JEWELRY: Givenchy G Link Necklace Crystals Paved   

That is so, so powerful. It sounds simple, but it's actually so difficult, and it requires such a strong knowing of yourself to really stand in that position. When anybody tries to keep you in a place or put you in a place you don't belong, it's a warning sign to get out.

Yes, it is. Don't ignore those signs, because some people—and I know I'm this way—will justify it to death. If you have those flags flailing, if you have those spidey senses tingling, get the fuck out of there and listen to yourself. You're not wrong.

Is there one thing that sticks out to you that was really difficult along your journey, or a blessing in disguise?

I’m full of those. All of those things I've thought were the end of the road, the end-all-be-all, my one chance [...] For me, the ending lesson is always: It's only failure if you stop. I don't think that I've failed yet because I'm always going.

When you don't get the outcome you want, change what you want or shift the mission. I don't like to be wrong. I don't like to feel like I wasted my time. So I keep going and make that time worthwhile. I always find a way to get that win.

This story appears in GREATEST Issue 05, a print magazine published by GOAT. Available now at select stockists worldwide.