Stop Asking Issa Rae About Fixing Hollywood — She’s Already Doing It

Issa Rae is a boss. Literally, since in addition to acting, the multi-hyphenate star runs her own production company and multiple other business ventures, where she manages a bunch of people — but that doesn’t mean Rae’s a part of “girl boss” culture, the pseudo-empowering, white feminist movement to profit off patriarchal norms. That’s not Rae at all. 

It’s unfortunate, though, that the word “boss” has been co-opted by corporate faux-feminism, because there’s no other way to describe Rae, who inspires women authentically through her work and exudes confidence in a way that’s unique to her. When I meet Rae in her Inglewood, CA office, we sit down to chat and she leans back in her chair, one leg up on her desk, the other flung casually to the opposite side, taking up space — like a boss.  The space itself — a temporary home for Rae and her team — is a shared one, and it’s unmistakably Black, from the artwork on the walls (like a painting of Yara Shahidi) to the people working in it. The 35-year-old Rae is wearing sweats (a navy-blue Destination Crenshaw set) and her feet are adorned with the Pharrell x Adidas “Human Race” collaboration shoes. Rae has just come from an editing suite where she was putting the final touches on her hit HBO series Insecure’s upcoming season finale. 

“Season 4 is going to be lit,” Rae says, with the certainty of someone who already has three seasons under her belt and a slew of other highly anticipated projects on the way. Rae is smack dab in the middle of a career-defining moment — transitioning from TV darling to leading movie star — but she’s taking it all in stride. “This moment feels like a lot of opportunities are being presented to me and it is just about taking advantage of them and making the right decisions,” she shrugs. 

Rae’s desire to make the most of her current moment may be why she’s so calm. The no-makeup, sneakers and tracksuit ensemble are an indication that she is knee-deep in post-production on the show that catapulted her from Internet-famous to an Emmy-nominated household name, but otherwise, there’s no sign that she’s giving in to stress or fatigue from her demanding schedule (she wakes up at 4 a.m. every day). While she’d been editing Insecure, Rae had also been on a whirlwind press tour for the romantic drama, The Photograph, opened a coffee shop she co-owns minutes from the office she’s in now, and started her own record label. Now, she’s in press mode for another blockbuster film called The Lovebirds, an action comedy co-starring Kumail Nanjiani, which she also co-wrote, as well as starting production on HBO Max series Rap Shit, on which she is an executive producer. Whereas I’m tired just typing out all the projects on Rae’s plate, she swears she isn’t.

“I’m just excited,” she says. “It’d be great if I could just be creative all the time, or if I could just be building businesses all the time. Those are all the fun parts, but there's press and photo shoots that come with it. All those things that I don't necessarily enjoy are what make me tired.”

Rae’s discomfort with doing press and fielding personal questions reveals itself early in our conversation. She’s most at ease when she’s talking about work – and sure, there’s a lot of it to talk about – but what’s going on in Rae’s life beyond her 187 (give or take) jobs? Well, she watches Love Is Blind, of course. “I was very upset with Jessica,” Rae starts, echoing the sentiment of anyone who has watched Netflix’s buzzy reality dating show. “But I was very upset with Mark too, because it’s like, have some respect for yourself, man!” As we get deeper into Rae’s Love Is Blind hot takes — “I love that Cameron is into Lauren” and “I fucks with Amber and Barnett; she really loves him” — I realize that  Rae is able to be funny and approachable without giving too much away. It’s a skill that most people would like to have. But for a celebrity? It’s a superpower. 

“I’ve never been really one to share my business, even with my friends,” Rae says.  “My very good friends will be like, ‘Girl, wait — what? Who is this? You've been with him for six months and we're just finding out?’”

Born Jo-Issa Rae Diop in Los Angeles to a Senegalese doctor and teacher from Louisiana, Rae spent part of her childhood in Potomac, MD, before moving back to California with her family. She felt a struggle to fit in, and her quest to find her identity would later become material for her award-winning web series, The Misadventures of Awkward Black Girl. I was fresh out of university when Awkward Black Girl was at its most popular, and watching it was like getting hit with a brick of recognition, and like I was catching up with a friend. Maybe that’s why, at every step of her career, I’ve cheered for Rae’s wins like she is my friend. Of course, like any real friend would do, Rae just laughs when I tell her this, and says, “That was so earnest.” I’m not alone, though, in my connection to Rae. Awkward Black Girl ran from 2011 to 2013 and made Rae a hero for uncool Black girls everywhere who felt, well, insecure. It was unprecedented, the kind of representation we’d been waiting for. When Insecure dropped on HBO in 2016, Rae became the Beyoncé for girls of color who didn’t feel like we had our shit together. And now, she’s built a brand off that relatability. But the thing about Rae is, while we may feel like we know her, we actually don’t — knowing someone’s opinions on Love Is Blind isn’t the same thing as knowing them, and I’m reminded of that whenever I try to get personal with Rae. 

In her forthcoming comedy-murder mystery, The Lovebirds (the release date of which has shifted due to mounting coronavirus concerns), Rae plays Leilani, a woman on the brink of a breakup with her boyfriend Jibran, played by Nanjiani, and there’s a whole bit about whether the couple would win The Amazing Race. When I ask Rae how she would fare on the show in real life with her partner, she balks. 

“I don’t have a public boo,” she says carefully, and I notice she’s not wearing a ring. I assume she just means she doesn’t talk about her relationship publicly, after all, at the time of the interview, the internet is pretty sure Rae is engaged. But, she clarifies: “I mean, I don’t have a public boo — or a private boo.” Rae says she can pinpoint the moment in her life when she became more wary of “telling my personal business.” While I’m expecting it to coincide with her rise to fame, it actually happened when Rae was just in the ninth grade. “I was telling my relationship stuff to one of my friends, and she was like, ‘Bitch, don't nobody want to hear that stupid shit.’ And I was like, ‘Okay, she's right. Nobody wants to hear that shit.’”

Rae does open up about one aspect of her relationship history in relation to The Lovebirds, though. She explains that depicting two non-white people falling in love onscreen was significant to her. “It was about showing what the world is like to me,” she says. “How do I say this? I have personally... never mind.” She’s lost her nerve, but after some coaxing, she relents. “I have never dated a white person. I've actually never dated outside of my race, period. But my friends are in interracial relationships and it bothers me that whenever interracial relationships are depicted on screen, they are with just white people. It's another way media in general centers whiteness.” 

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The Lovebirds was initially written for “a generic white couple,” Rae tells me, but when Rae and Nanjiani signed on, they made a point to rewrite the script so it was more specific to the experiences of people of color. It’s a fun comedy without an overt social message, but there are moments that nod to the realities of walking through America looking like Leilani and Jibran, like how the cops are likely to trust some people over others. “The acknowledgement that the police aren't going to believe us was important,” Rae says of tweaking the script. “You don't get the benefit of the doubt in these situations. They're not going to be like, ‘Hey, Brown man and Black lady, y'all didn't do this, right?’”

Aside from those real moments, the movie hinges on Rae and Nanjiani’s hysterical chemistry. Rae says the two became good friends while shooting (we have her to thank for the beard Nanjiani sports in the film, since she convinced him to grow one) and they bonded over their shared obsession with their respective caloric intake (“we were just masochists together,” Rae laughs). This was in the months leading up to Nanjiani’s internet-breaking shirtless shot where he showed off the body he built for his role in Marvel’s The Eternals. “When I saw that picture, I was just so proud of him,” Rae says. “He looks like a Chippendale's dancer.” 

Nanjiani isn’t Rae’s only leading man who also happens to be an online thirst trap. In The Photograph, she embarks on an epic love story with Lakeith Stanfield, another popular Internet Boyfriend. Rae refuses to entertain my theory that Stanfield is the best kisser of all of her costars, but she does delve a bit deeper into why her recent roles have gravitated toward romance. She credits Queen Latifah, Sanaa Lathan, and Nia Long for being Black actresses who paved the way for her to star in these films, and says she “maybe subconsciously, probably consciously” has been choosing these roles to prove a point about representation in Hollywood. “To have the opportunity to be the lead role in [romance films] is very flattering,” she says. “And I do recognize that not many people who look like me have gotten to do this. So, I don't take that lightly.”

Rae may be taking her roles seriously, but there’s one thing she won’t give energy to: online commenters weighing in on the storylines of Insecure. Here is where Rae, generally a Black Twitter fave, has faced her most vicious criticism. She swears she doesn’t pay attention to the backlash, unless it gets loud enough that she can't ignore it. So far, the most notable time this happened was with Insecure’s #condomgate. Viewers expressed concern that the series wasn’t showing its characters practicing safe sex. “In my mind, I was like, shut the fuck up, y'all don’t need a show to tell you to use condoms, like, shut the entire fuck up.” But, Rae says she changed her mind when it felt like the audience was being taken out of the story, so the show figured out subtle ways to work condoms into shots. “Yeah, that was a priority. But do I feel the responsibility to tell adults to put on condoms who are watching HBO? No.”

The responsibility of being one of the few Black women in her position in Hollywood seems like it would carry an insurmountable weight, especially when it looks like her work is unfairly put in the position to be all things to all Black people. For example, when her co-star and fellow writer Natasha Rothwell posted a picture of the Insecure Season 4 writers’ room to Twitter, which included a smattering of items like Hennessy, Cocoa Butter, Jamaican castor oil, and Frank’s Red Hot Sauce, with the caption, “if you were wondering if the S4 [Insecure] writers’ room was Black AF, the answer is yes. Yes, it is.” Twitter had a field day. People were tweeting that the pic not only showed the wrong (read: not the “Black”) brand of castor oil, but also that the hot sauce should be removed, because Black people don’t use Frank’s. Some responses even called the post “performative blackness.”

“I was off of social media during that time,” Rae says, recalling going to the writers’ room and finding Rothwell reacting to the comments. “Tasha was like, ‘What the fuck?’ and then she showed me the picture and I was like, Well, we got Crystal Hot Sauce, why would you put Franks? But, okay, okay, okay, that's not the point,” Rae laughs. Her point is that the show will never be able to represent the entire Black American community. “I always said that from jump that we'll never be that. But when there's so few shows, that expectation is inevitable,” she says. “There's nothing I can do about what people say about the show or what they think about the show; all I can do is just tell the story that I want to tell. If it's not for you, then it's just not for you. Move on.” 

Similarly, Rae hopes she can move on from talking about diversity in Hollywood. “Journalists and everybody else need to start asking white men these questions like, ‘How do you feel about diversity? What are you doing to combat it? What's the next step,’ as opposed to asking people of color,” she says. She’s right, but when Rae has spoken out about prejudice in the industry, her words strike a chord. Rae’s red-carpet quote, “I’m rooting for everybody Black” at the 2017 Emmy awards is now a go-to meme and rallying cry. More recently, her offhand comment while presenting this year’s Best Director Oscar nominations of the all-male nominees (“Congratulations to those men,” she deadpanned) put her back in the position to field questions about the state of inclusion in her industry. “I just really don't think there's anything more that I can say. I'm doing it. I've been doing it,” she sighs. In 2014, Rae founded ColorCreative, an organization whose mission it is to uplift underrepresented writers in film and TV. The young woman who inspired Rae to start the initiative is now a writer on Insecure and wrote “one of the funniest episodes of the new season,” Rae says. 

The most frustrating part of the diversity conversation for Rae is finally having that coveted seat at the table and being in boardrooms with powerful execs in the industry just to realize that the only people rooting for everybody Black are other Black people. “Only people of color think about other people of color and really, only Black people think about Black people. No one else has the determination to employ us or to make sure that we're seen and represented,” she says. “And the more I work, I go into spaces and I’m thinking, Everybody here is a white dude and nobody is like, ‘What are y'all doing?’” Her voice raises into a screech of incredulity to emphasize her last point. The lack of support from the gatekeepers in the industry is why Rae says she’s constantly creating spaces for Black creatives that she didn’t have when she was on the come-up. 

One of those spaces is her record label, Raedio. As Megan Thee Stallion’s struggle with her label and Taylor Swift’s crusade to own the masters of her songs have dominated headlines, it’s inspiring to hear Rae emphasize that she puts artists first at her label. Her priority was to make sure all of her artists own their own masters, have health insurance, and make good money. “Right now, when people are rebelling against record labels and are distrusting of them — in many cases rightfully so — we wanted to make it feel like a welcoming environment.” Rae says the idea to start a label came after she was approached to become an artist herself by other labels that were impressed by her Insecure mirror raps (“I was like, ‘These aren't good. Do y'all know that?’”), but that the idea of starting a label to support emerging artists was more appealing to her. Her first artist, TeaMarrr, released her first single last month. Bringing up the next generation of Black women behind her in the entertainment industry is what Rae says is the most rewarding part of her career. “[TeaMarrr] is fucking talented and all she needed was the shot and the platform,” says Rae. “Sometimes all you need is the push and then you're just like, Okay, thank you for the runway. And I'm going to shine.”

You could argue that Rae has already lifted off from her runway, but she still feels like this year could make or break that trajectory. The success of The Lovebirds and fan reception to Insecure season 4 are the unknowns that could drastically alter the future of her career. “There are some things that are just beyond your control — you could plant all the seeds and there's a drought or you can plant all the seeds and it floods,” she says. “I think this is one of those things where I did the work and it can either be great for the future or not.”

That’s a lot of pressure, even for a boss like Rae. So, is she feeling it? 

“If somebody else is pressuring me I automatically go into fuck you mode,” Rae says, leaning forward and smiling. “Because I just know nobody's putting more pressure on themselves than I am.”