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Issa Rae Embraces Her Role as a Hollywood Trailblazer: “You Can’t Be Polite or Modest”

Multiple nominee Issa Rae, could make history at this year's Emmys, but her main priority is making way for diversity at her production companies and beyond. 

Throughout the course of Issa Rae’s career, she’s absorbed plenty of good advice. But none has been as impactful as the wisdom she received in 2015 while surrounded by Ava DuVernay, Debbie Allen, Shonda Rhimes and Mara Brock Akil at an Essence cover shoot. At the time, Rae was 30 — a relative newcomer to the tier of power and influence occupied by the women around her — and trying to find the best person to direct the pilot of Insecure, the HBO dramedy series that she created, stars in, writes and produces. Rae listened as each woman emphasized pivotal career flashpoints, when they’d dropped being polite and stood their ground.

“I remember feeling, ‘Oh, this is a life-changing moment for me,’ ” says Rae, 35, sitting outside her not yet-renovated Inglewood office space, which will house her growing empire of two production companies and a record label. “I ended up making the call that I needed to make the next day,” she adds. That call involved saying no to a director she didn’t think was a good fit for the show. “Years later, he came up to me at a party and was like, ‘Yeah, I would’ve fucked your shit up. You made the right choice.’ I felt so validated.” (When asked, Rae says, “I absolutely cannot say who, but if he wants to fess up after reading this, be my guest.”)

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Through the lens of a young Black woman, Insecure — a show comprising a predominantly Black cast and writers room — imparts savvy storylines that touch upon ex-boyfriend drama, gentrification, class, motherhood and code-switching (adjusting how one speaks, appears and behaves to make others feel comfortable). Through the series, Rae depicts what everyday life feels like for her and her friends in Los Angeles. Traditionally, Black characters have been “focused on specific struggle stories, or we’re just side characters, or we’re just supernatural, and there was never any real in between,” she says. “That’s something Prentice [Penny, Insecure’s showrunner] and I talked about— that white people get to have scenes with them just washing their hands and thinking. We don’t get that shit.” With healthy ratings (its fourth season had 4.5 million viewers per episode across all platforms), Insecure is arguably the most impactful show to normalize Black lives onscreen in the past decade.

Now four seasons strong, the Peabody Award-winning series is up for eight Emmys, including two for Rae: lead actress, following her 2018 nomination in the same category, and comedy series. If Rae wins for lead actress, she’ll make history as only the second Black woman to take home the Emmy in the category since Isabel Sanford for The Jeffersons in 1981. If Insecure wins for comedy series, Rae will be the first Black woman creator of a premium cable show to receive the award. And as exec producer of HBO’s A Black Lady Sketch Show, she is also in the running for variety sketch series. But Rae’s not here for the accolades. “Awards don’t validate you,” she says. “They allow more people to know about the series, like, ‘Oh, what is this?’ That’s all you want.”

In 2018, Rae’s production company, ColorCreative, struck a multipicture deal with Columbia Pictures to develop projects from diverse writers. In early August, it was announced that Rae would executive produce Seen & Heard, HBO’s docuseries on Black television, for her other production company, Issa Rae Productions. She’s also teaming with Jordan Peele for the sci-fi feature Sinkhole  while juggling her first feature, Perfect Strangers; Badmash, a Bollywood crime-comedy picture; and HBO Max series Rap Shit, about female lyricists. Says Kerry Washington, who directed an episode of Insecure in season four: “Issa’s vision extends beyond the limitations of Hollywood’s imagination.”

In addition to penning features, Rae, who starts her day at 4 a.m., has also been starring in them. From 2019’s Littleto February’s The Photograph, to The Lovebirds, which switched from a theatrical to a Netflix release in May because of the pandemic, Rae is onboard for all of it: “Selfishly, I was like, ‘Oh, I get to be a romantic comedy lead.’ I was almost flattered to be thought of to do something like that.”

While many actors relish jumping into the unfamiliar, for Rae, the key to her success has been mining what she knows. Born in Los Angeles to a Senegalese doctor and a teacher from Louisiana, Jo-Issa Rae Diop, who is one of five children, spent part of her childhood in Potomac, Maryland, before moving back to L.A. Two web shows — the first, Dorm Diaries, centered on Black students at Stanford University; the second was YouTube series The Misadventures of Awkward Black Girl  — led to Insecure. “Nobody’s you,” she says. “How you exploit that as a creative means so much.”

By 2013, a year after a half-hour comedy called I Hate L.A. Dudes  (sold to ABC by way of Rhimes’ Shondaland) fell through, Rae was in talks with HBO for Insecure, which premiered in 2016. Now in the (virtual) writers room for season five, Rae discusses getting back to production during COVID-19, pay parity and what it means to craft a legacy: “To be able to have the ability to bring other people in, who I think are massively more talented, it’s something that brings me so much excitement.”

I felt like this season, more so than any other, was a love letter to our neighborhood, View Park.

I love it. I’ll walk in my neighborhood all the time because that’s the only exercise I’m willing to do. This lady came up to me and she was like, “Yo, I really love that you feature our neighborhood.” I was like, “I regret it.” It was a hidden gem, but I had to open my mouth.

Even after going to Stanford, you came back. 

[When] I was in New York, I was in the Black neighborhoods, like Washington Heights and Harlem. I was convinced that I wanted to make it out there — whatever that meant. I would come back and visit and a friend reminded me, “Girl, this is home and why don’t you just come back here? Everybody knows you here.” I had to get a new appreciation of L.A., and then just loved it so much.

Then I lived in Inglewood while we were coming up with the idea for the show, and knowing just how Black it is and realizing that it hadn’t been portrayed in a way that I felt was accurate to how it is now … It just really excited me to set something there and make it a character. But no one really invests with the community in mind. That always bothered me. I remember being in Inglewood, like, “I want the benefits of gentrification without the gents.”

Taking it back to Stanford, you studied African American studies, not film. 

Yes, but I studied theater and took drama classes and creative writing classes. I thought I wanted to be a director until I started to do it. It felt like too much control. I’m not necessarily [about] the visual aspects. Like meeting Melina [Matsoukas, who directed seven episodes of Insecure], I was like, “Wow. You pay attention to every single detail and you get bothered by everything that’s out of place.” I just don’t care enough.

After Stanford, you pursued a New York theater fellowship. How were those days?

In college, I also thought that I wanted to pursue theater. Then when I got to New York, I was like, “Oh, this is real theater. I don’t like this.” It was a little too abstract. And admittedly felt really, really white in a way. But the Public Theater was all about facilitating playwrights of color and creating this pipeline to Broadway. It sparked an idea for me to form a collective of Black filmmakers to make our own work and, I think, subconsciously laid the foundation for some of the work that I did later.

Eight Emmy nominations for Insecure this year, the most so far. What is this moment like, and for co-star Yvonne Orji to also be nominated?

Anybody can tell you when I heard Yvonne’s name, that’s when I got really excited. I had been nominated before, but I’m very much aware that I don’t do this by myself. I did feel guilty. It was just like, “Everybody else is killing it and they’re really helping to elevate me and they’re not getting the recognition.”

But Yvonne was like, “They’re watching and they’re seeing the work we’re doing.” To be a four-season show, to have it happen now, is not lost on me because there’s so many new and amazing shows. To have the culture support our show, it’s a FUBU [For Us, By Us] show in every way … I feel so blessed and we love every second.

Was there ever a moment back then when you had doubts?

[With] Insecure, it took so long and every draft was like, “No, this isn’t it. No, this isn’t it. No, this isn’t it.” I was just like, “Oh, OK. Maybe this is the end of the road for me,” especially when I’m investing in this big venture, which ended up being ColorCreative, and spent all my money and didn’t have anything. I remember being on the set of a pilot we were filming [Words with Girls] and getting the call that HBO was not feeling the latest draft and I was losing Larry [Wilmore, Insecure’s first showrunner]. I was like, “This isn’t going to happen for me, and I just did all of this for nothing.”

Thankfully, Larry leaving for The Nightly Show, as much as I love him, was the best thing that could’ve happened because it forced me to be like, “OK. It’s not a workplace comedy,” and having a conversation with HBO was really helpful just in terms of centering it. It was just like, “I’m going to put everything that I’m going through out on the table in this pilot. If they say no, at least I tried, and fuck it.”

Hollywood definitely isn’t an industry that was made for us [Black people] to have longevity.

By no means.

How does it feel to be defying that and to say, “Fuck that. I’m here. I’m staying.”

I do question that. I still [do]. For me, my longevity will be opening the door for others. I think frequently about the Tupac quote: “I’m going to be the light that sparks the inspiration, that sparks the change.” I need to get that quote right. [Exact quote: “I’m not saying I’m going to change the world, but I guarantee that I will spark the brain that will change the world.”]

Why do you feel like this season really stood out for Emmy voters?

I’m going to be real. I think the pandemic, being quarantined during a period when our humanity was questioned, in a more front-facing way, definitely helped. We came on during a time when people were bored at home, and also there were racial uprisings, and our show served as a comfort. Thank God, because to release anything else during this time — even our show — I felt a huge guilt in coming out during the protests because there were just so many more important things happening, I didn’t want to take full focus away from that. But to hear people be like, “No, this is an escape. It brings us back to Black people being joyous and happy and ourselves” — our natural state really felt like we were meant to air during this time. I think that for sure helped people to see our show in a different light.

In processing the guilt that you felt, were there ever moments of “Should we alter a storyline?”

Not alter the storyline. Me and some of the actors were on a group chat. First we were talking about, “We should protest. How are we going to get together?” And it came down to the show, like, “Do we even do anything? We shouldn’t promote this shit, right?” And then we got on the phone with HBO just to get behind the messaging and what we wanted to say, to make sure that people didn’t think that we were being tone-deaf to what was happening. So they were also very helpful, and Natasha [Rothwell, series regular, writer and supervising producer] wrote a beautiful statement that we were able to piggyback off, just, “We’re aware of this time, and we’re also aware of the beauty of us, and we don’t want anything to negate that.” That’s how we were all feeling in the episode that aired during that one specific Sunday [May 31]. It just so happened to align, in a very dark way, perfectly.

So many of us were just feeling the same feelings of dread. I was so worried, too, just thinking about, before I went out there, the people who were out there in the streets, and how historically, our voices had been suppressed, and we’ve been baited by various fear tactics, and I was just like, “They’re going to target people. They’re going to try to make it so that nothing changes once again.” That was a devastating part: Is this just going to be for the moment? And then, are we going to forget about this? But from what I’ve seen behind the scenes and some of the people that I’m working with, there is a dedicated energy to making sure that this time is for real, and that we’re making real impact moving forward.

How do we keep that momentum going?

I think it is going. It’s a terrible expression now, but it’s keeping our foot on people’s faces in that way of, “Don’t forget this. You posted a little black square, but we’re still about this life, and if you’re serious, then do something about it.” And I’ve seen a real commitment to people wanting to change.

Have there been times when someone, maybe perhaps with more power, wanted to override a certain vision?

All of that was early on. I remember the biggest thing back and forth we had was with the former president [Michael Lombardo], and the show title. He wasn’t super insistent about it, but he was passionate about the fact that he didn’t think that Insecure fit because he was like, “I see these strong, confident Black women, and they’re fierce.” And all the terms that we use to describe ourselves, but I was like, “Ooh, that’s not … No, they’re not specifically.” And [that’s] exactly what we want to showcase throughout the show … the title reflects that, and as soon as I explained that that’s what we’re trying to combat, he got it and backed off.

Beyond those early script stages, they’ve been really, really supportive, and they’ve never pulled us to the side, “Can you explain this first because the audience …” They don’t care about your broad appeal, which is why I also wanted to make a home with them, because the ratings on it were dry then, and they’re very aware of being a subscription-based model. We’re going to appeal to who we appeal to, and there’s no pressure there. They were also really good about not leaving us in the dark about whether we were going to get picked up. That first season, I was scared as hell, but since season two, they’ve been really great about letting us know that we have a home.

I wonder about the dynamic of the room being predominantly white execs. Do you think that anything would be different if those rooms reflected the way the world really is?

A hundred percent. There’s no question that some of the input that we would get would be different. I’m also really happy that there aren’t a lot of executives on our show. Part of the intimacy is that we have two people [Amy Gravitt, HBO’s comedy head, and Amy Hodge, vp original programming], where at a network, you have two people here, three people here, two people there, and it’s just so many voices. Can HBO improve in terms of their hiring practices? A thousand percent. They’ve got to do it.

Insecure deals with issues of sex and race and class, but you guys never seem to jump into the topical fray. You’re never like, “This is the Black Lives Matter episode.”

Yeah, I feel like it’s corny. We’re not an after-school special. That’s not how we live life. I don’t wake up like, “Today’s about to be about Black Lives Matter.” When you experience racism or sexism, your life doesn’t stop, but it may affect how you talk to your partner that night when you get home or prevent you from doing something else. Those are the moments that I’m more interested in.

How do you see the pandemic impacting plot, and how do you intend to shoot?

I don’t want to mention COVID or the pandemic in any way, shape or form. We are addressing the fact that the city is going to be different, and part of the way that we’re talking about it is putting people with masks in the background or subtle things like the business being impacted because we’re so location-specific. We’re supposed to shoot in September, so that’s not happening. It changes every single day. It’s definitely a painful reminder that you don’t control your plans.

What are some of the new pressures you’re facing?

The longevity of it. I really want to make sure that what I’m doing has impact and is long-lasting. I want to feel rooted …

What would make you feel rooted?

Girl, this is for my therapist that I don’t have. I don’t know. It always changes. It’s old age and still being here. Denzel-ness. Alfre Woodard-ness. I mean, Denzel is a good model because he belongs to Black people and has never denied who he is and his roots. The stuff that he’s done underground to help young Black actors, to create a pipeline for them. He’s also been a producer and a director and is just so revered and has a Blackass family. I got to go to his AFI tribute, and I was just reminded, “Man, this man has meant so much to me, my mom, my aunt, my grandmother, and that matters to me.” There’s a legacy there.

You are now in a position to demand more money. What does that feel like?

We’ll find out. I mean, I’ve definitely demanded. Yvonne joked before the Emmy nominations came out, “Girl, I told all my agents, ‘Don’t make no deals until after Tuesday or Monday,’ whenever the announcements were, because our price is going up or down.” So there is something to that, too, of just realizing your worth. Also, seeing how little these white people care about asking for more than they’re worth in many cases. You can’t be polite, or tiptoe, or be modest about those things. You’re seeing these nine-, 10-figure deals out there. I have a great team that also is not afraid to ask for beyond my worth. I have an amazing Black lawyer who is constantly being like, “No, I’m going to get you better.” Or, “No, I’m going to make sure. I heard that so-and-so made this, you’re about to make this.”

Criticism — how does it affect you?

I’m open to all criticism. I feel like you have to be, to be in this industry. There are Black critics that I value what they think because I read what they read, or I read what they write about everything. I love it. I can see this point of view, and that’s so interesting. It may be reflected in something else that I do down the line, or it may spark inspiration for conversations that we may have. We feed each other in that really interesting way.

But let’s be real. There are a couple where I’m like, “Oh, this person just comes for me,” or “This person doesn’t like me.” You’re putting your personal life into it. You’re a blogger, not a critic at this point. It’s an art form.

How is one of your first forays into feature writing going?

I’m excited. I’m doing a feature, an adaptation of an Italian film called Perfect Strangers. It’s set at a dinner party with friends where they decide to read all the messages that come in on their phones. That’s a game that I would 100 percent play. There’s something about the cultural specificity of it that I wanted to bring to a movie. It’s been remade in different countries, like in South Korea. I just felt I could bring my own spin.

Jordan Peele and Sinkhole: Please tell me how this went down.

Shoutout to one of our execs who found the short story. The premise is, basically, a couple moves into a house that has a sinkhole. When you drop things in it, the sinkhole makes everything perfect. The quest for female perfection is really intriguing to me and what that means now, especially in a culture that’s still resistant to feminism. There’s just something so eerie about that quest to me. Also, what Black female perfection looks like, and relationship politics — when you have a particular dynamic that’s working for you as a couple. We’re just in that brainstorming phase now.

Sara [Rastogi, who is the vp development at Issa Rae Productions] was like, “What do you think about bringing it to Jordan Peele or pairing with them?” So it was as easy as that. They were into it and then it was up to us to convince the writer, a young white female writer [Leyna Krow], that we were the best people for the job. She said in an interview what intrigued her the most was that the ideas that we had extended beyond her perspective. She was like, “I’m a writer and I think about white people when I write.” The idea that we could bring something else to the table in a way that she hadn’t thought of really excited her.

To be in a competitive situation like that — we’re a very small, independent production company, [and] obviously Jordan Peele is just massive in terms of what he’s been able to do in such a short time, as a director, for the culture — the fact that he even wanted to partner with us was really amazing. We’ve hit each other on the DM and we’re really super excited.

So during this shutdown craziness, what have you learned about yourself?

I’ve learned that I obviously, like so many people, value touch. I value social interactions. I also realize I don’t work as hard as I need to, to preserve certain relationships in my life. I need to do better about that. That’s been a hard revelation for me. I feel like this has caused me to withdraw in a way that I’m not happy with. I’m trying to reconcile that.

I know some of your co-stars seemingly put you on blast about being engaged. When it comes to your personal life, why do you prefer to keep things private?

I guess because it’s private. Whose business is it? I realized I just don’t like to be the subject of conversations if it doesn’t have to do with my work. I’ve always been like that, where I’d be dating someone and my friends would find out six months later. Like, “Bitch, what the fuck? Why don’t we know this?” So it’s just always been that I want to vet situations for myself. I really value that part of my life a lot.

Who should Hollywood be paying attention to talentwise?

Oh, so many people. There’s a writer named Tori Sampson who’s out of this fucking world. She’s a playwright. Writer Syreeta Singleton. Child is another person, a director. Everything she makes is beautiful and she just did a video for Big Sean on a whim. Now she’s the go-to video person. TT the Artist is someone else who’s a multihyphenate, in a way where she started off making music and made a documentary [that] was supposed to be at South by Southwest. You know how we have crumping here? There’s a different form of dance in Baltimore where people are dancing their pain away, in spite of their circumstances. She made the most beautiful documentary [Dark City Beneath the Beat] I’ve seen. Have you watched I May Destroy You?

Girl, obsessed.

So fucking good, but I was like, “Hollywood is paying attention.” It’s amazing. It’s really disturbing. The conversations that have [been] sparked around it are just so necessary. I almost wish it had come sooner. It’s going to be so impactful to a generation of people.

Do you know her?

Yeah. I knew her from when she was doing Chewing Gum. I knew this show was coming because we have the same exec at HBO. She told me about it, about how this was her story. I was like, “We’re an HBO comedy. So she’s going to make this a comedy, like this terrible experience where she got roofied and raped?” The fact that it still manages to be darkly comedic and also just flat-out funny is just phenomenal. We got to kick it in her Chewing Gum days and I’ve kept in touch. I get to watch this as a massive fan. It makes you want to create more.

Interview edited for length and clarity. 

This story first appeared in the Aug. 19 issue of The Hollywood Reporter magazine. Click here to subscribe.