Issa Rae Is Not Willing to Compromise

Dress, Christopher John Rogers, $2,350. Earrings, ring, Bulgari.

Cass Bird

Issa Rae wakes up at 4 a.m. every day. Being an early riser, she says, is her self-care. “Those couple of hours are the only time that is just mine,” Rae explains. Perhaps waking at such an hour is a requirement when you’re busy taking over the world.

Born Jo-Issa Rae Diop, the creator/writer/producer/actress/entrepreneur rose to fame in 2011 with her YouTube series The Misadventures of Awkward Black Girl. The show’s massive success earned Rae a Shorty Award for Best Web Show and a spot on Forbes’s 30 Under 30 list, and spawned her hit HBO series Insecure, which aired its fifth and final season last year. This July, when Rae was nominated for her third Outstanding Lead Actress in a Comedy Series Emmy for Insecure, it was a meaningful end to that chapter of her life. “It felt really great because our last season aired in December [2021] and I thought that people would forget about it,” Rae says. “To get a nod in the last season means a lot.”

Now, as she navigates a post-Insecure world, Rae is beginning her self-proclaimed “mogul era.” Just this year, she premiered her new series Rap Sh!t and the second season of her reality series Sweet Life: Los Angeles, both of which are on HBO Max and produced by her media production company, Hoorae. She’s also appearing in Greta Gerwig’s Barbie, slated for release next summer. Her ultimate goal: owning a studio in South L.A. “That has been in the works for quite some time, so that would be like, ‘Okay, I’ve done what I set out to do.’” But while she works toward that day, her career has already far exceeded her wildest dreams. “[As a kid], I knew I wanted to write, but I definitely did not have a vision of what I’m doing now,” Rae says. “I just didn’t know what was possible.”

Bra top, $1,180, pants, Moschino. Earrings, Cartier. Necklace, Bulgari. Wedges, Pucci, $1,040.

Cass Bird

On creating Rap Sh!t

“You’d think that if you did one television show, the next one would be easier, but it just wasn’t. In so many ways, I feel like I should’ve prepared myself more to produce this. I’m so grateful that we had partners at HBO Max who were super patient with our learning curve. I wrote the pilot script, and a lot of it developed over time. The visual language was really ambitious, and we had to make sure that we got it right. You don’t get those opportunities at other networks.

“I also learned just how particular I am. I learned that via a colleague who called me out on it. He didn’t mean it offensively and I didn’t take it offensively. In fact, I was complimented. I have a very specific way that I envision things and a very specific taste for things. I’m not really willing to compromise on it. I love the show and I’m really proud of the fact that it’s primarily led by Black women and run by Black women. That’s a huge accomplishment.”

On being a boss

“I was just talking about how much I hate it the other day. [laughs] I love the work, but leading [a company] is a completely different beast. It’s a full-time job. I realize that I can only do the full-time job when I’m not creating, which is kind of a nonstarter for me. So trying to find that balance and make sure that these brilliant people that I’ve hired have vision and direction is my main priority, but it requires a different part of my brain to run.”

I can control my own environment and who I work with…All money isn’t good money. All people aren’t good people.”

Bandeau top, $650, skirt, $850, Mônot. Earrings, Cartier, $4,100. Sandals, Christian Louboutin.

Cass Bird

On working with her heroes

“Regina King directing an episode of Insecure [was amazing]. I have had such a distinct journey with her. She has supported me since Awkward Black Girl. I remember I was coming out of Larchmont Bungalow Café and I saw her. She got out of her car and was like, ‘Awkward Black Girl! What’s up?’ And I’m like, ‘Regina King, stop it. You do not know me.’ I heard that she was going into directing, so when I finished the pilot for Insecure, I reached out. But at that time she was like, ‘Oh, I’m not directing right now because I’m doing this series set in Texas,’ which ended up being The Leftovers. Then she circled back and was like, ‘Hey, if that offer still stands, I still want to. I love Insecure so much.’ So, that was surreal. I just have so much love, respect, and admiration for her. She is L.A. royalty to me.”

Shirt, Etro, $850. Hoop earrings, Cartier, $7,700.

Cass Bird

On what has changed for women in Hollywood post-#MeToo

“Sadly, not much. It feels like we’re regressing, depressingly so. There are just too many enablers for there to be real change. People have to be held accountable. There have to be legitimate consequences. Hollywood is very bad about consequences. It’s literally the worst industry when it comes to punishing people for misdeeds and actions, because money will always reign supreme. That’s something that, even by working in this industry, we’re enabling. So it’s hard. What I have realized is that I can control my own environment and who I work with. I can hold people accountable within my world and my bubble. I don’t have to work for everybody. All money isn’t good money. All people aren’t good people.”

On what more needs to be done

“It starts with a backbone. While I don’t support people jumping to immediate conclusions and I think it’s entirely fair for investigations to happen, I think it’s extremely important to, like the mantra says, ‘Listen to women.’ I’m gonna be real, the stuff that’s happening with Ezra Miller is, to me, a microcosm of Hollywood. There’s this person who’s a repeat offender, who’s been behaving atrociously, and as opposed to shutting them down and shutting the production down, there’s an effort to save the movie and them. That is a clear example of the lengths that Hollywood will go to to save itself and to protect offenders. So, don’t do that, and women may be able to thrive. They won’t have to live in fear of keeping silent because it’ll ruin their careers. It’s just a constant pattern of abuse that’ll only persist if Hollywood continues to insist on being this way.”

Bra top, $755, shorts, $880, boots, Moschino. Hoop earrings, Cartier, $7,700. Cuff, Van Cleef & Arpels.

Cass Bird

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On being a role model

“I don’t feel any responsibility. I’m like, ‘If you look up to me, proceed with caution. That’s on you. I’m sorry, while also flattered. But good luck to you if you do.’ I’m very transparent about my mistakes. I’m very transparent about my journey. But I don’t have to watch myself or what I do. If I had a legion of 12-year-old girl fans, I would be more cautious, but I don’t think that’s the case.”

On what she wishes she knew before starting out

“That a lot of people really don’t know what they’re doing and don’t know the answers. I think it’s so intimidating coming into this and being like, ‘They know exactly what they’re talking about, so when they’re giving me this note, it’s because they know what’s successful.’ Or ‘When they’re saying no to this project or this concept, it’s because they know what works and what doesn’t.’ No, they don’t. They don’t know anything. They’re learning at the same time as I am. They’re just as surprised when something is a hit as I am. These are just people who are winging it. You can do the same amount of research, the same amount of reading, and the same amount of studying as they can to be a step ahead.”

Shirt, $850, skirt, $1,790, Etro. Hoop earrings, $7,700, rings, $15,300 each, Cartier.

Cass Bird

On her only-in-Hollywood moment

“I was at the Golden Globes sitting at a table with the cast of Big Little Lies. Laura Dern was having a conversation with the president of HBO and was casually, unbeknownst to me, pitching him her next idea. It was him being like, ‘Okay, I love the idea. Who’s gonna write it?,’ then her pointing to me, and then us selling a show together. That, to me, will always be an only-in-Hollywood moment. Now we just have to make the show.”

(Pink): Dress, Christopher John Rogers, $2,350. Earrings, ring, Bulgari. (Yellow): Jacket, $598, dress, $398, Polo Ralph Lauren. Earrings, Piaget, $5,450.

Hair by Felicia Leatherwood; Makeup by Joanna Simkin for Dior at The Wall Group; Manicure by Eri Ishizu for Dior Vernis; Produced by Lola Production.

This article appears in the November 2022 issue of ELLE.

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Juliana Ukiomogbe is the Assistant Editor at ELLE. Her work has previously appeared in Interview, i-D, Teen Vogue, Nylon, and more.  

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