Issa Rae on the Return of ‘Insecure’ and Heavy ‘Burden of Representation’
After years of building a Hollywood empire to bring up other black women, the creator is grateful for a pause. “I missed a deadline yesterday and I was like, psh, f*ck that shit.”
It’s nice to be wanted. It can also be annoying as hell.
Second only to Rihanna—and if you’re going to be runner-up to anybody, it’s a pretty regal shadow to stand in—no one has been badgered more by fans about when new material is dropping than Issa Rae. In the 18 months since the season three finale of Insecure aired on HBO, Rae—who created, writes, and stars in the series—couldn’t so much as tweet without facing a coordinated assault campaign from fans demanding answers: Where’s season four!?
Obviously, Rae was touched. Wow. She created something that people really like that much. But also... chill.
“The only time it got on my nerves is when people were like, ‘Girl, what else are you doing? Stop being lazy! Put it out.’ That’s when I’d be like, ‘If you don’t shut the fuck up…’” She lets out a big laugh. The wait is over. Season four of Insecure premieres Sunday on HBO.
Yes, it’s been the longest hiatus between seasons in the show’s celebrated run, which has brought a Peabody Award, AFI Program of the Year mention, acting nods at the Emmys and Golden Globes for Rae, and, most important, historic status. Insecure is the first HBO comedy about the experience of a twentysomething black woman. Of course Twitter, specifically Black Twitter, would rally so passionately around the show. And those people wanted—needed—season four!
But Issa Rae has been busy.
She’s starred in four movies since the last episode of Insecure aired: the underrated drama The Hate U Give, studio comedy Little, sexy-as-hell romance The Photograph—her first time in such a leading role—and the upcoming rom-com The Lovebirds opposite Kumail Nanjiani.
She also executive produced A Black Lady Sketch Show, the first-ever sketch series with an all-black, all-female cast and writer’s room, and was the face of CoverGirl. She is developing the Bollywood crime comedy Badmash; will write, produce, and star in the adaptation of Italian dramedy Perfect Strangers; and was featured on the red carpet’s list of bold-faced names behind the new series that will launch HBO Max. Oh, and she launched a record label.
So let her live. As in, like, live. Insecure works because of how rooted it is in experiences she’s had and the evolving connections with her friends. A person needs time to have those experiences.
“People think that you’re just sitting on it and being petty,” Rae says. “When they don’t see you, they just really think you’re not working. So I was grateful to the people who are just innocently missing it. And fuck you to the people who, when I would post a picture of my mom, would be like, ‘Where’s Insecure though?!’”
She laughs again. She’s mastered that kidding-but-not-kidding inflection, speeding up her speech and punctuating her most brutal reads by going up an octave to soften the blow. It takes about 90 seconds of talking with the multi-hyphenate to feel like you’re gossiping with a friend. It’s an incredibly appealing vibe—so appealing that last year she was made a voice of Google Assistant.
So OK Google, how is Rae spending her quarantine? When the world screeched to a halt, Rae was set to fly to Austin for the premiere of The Lovebirds at SXSW and kick off three weeks of press for the movie, which was supposed to hit theaters last week, and Insecure. At some point, she was also on the hook for a screenplay and pilot script she is writing.
When SXSW and its theatrical run was canceled, Netflix scooped up The Lovebirds, to be released at a date TBD. After four years of building a veritable empire at breakneck pace, there was a pause. The silver lining of everything happening in the world meant time to catch up on that writing. But also... to not.
“It’s just like, what is time at this point?” she says. “What are deadlines? I missed a deadline yesterday and I was like, psh, fuck that shit. What am I stressing for?”
When it premieres on Sunday, Insecure joins a host of TV series doubling as unexpected balms as people are trapped at home weathering uncertain, unprecedented, and scary times and are desperate for distraction and blips of joy.
After watching Natasha Rothwell, who plays Kelly, nail the physical comedy of not-so-subtly hiding her desire to sneak a taste of her friend’s breast milk in a screener of the new season, I can confirm the new season as that source of joy.
Rae laughs so hard she has to take a recovery breath at the mention of Kelly and the breast milk. “That was something I didn’t notice until watching the final mix actually, like I had missed that so many times,” she says. “I laughed probably as loud as you did when I finally noticed it.”
There’s something pleasantly bittersweet about Insecure at a time like this.
The show has always been a love letter to a part of Los Angeles almost never portrayed and certainly not celebrated in pop culture—areas of South L.A. like Inglewood, where the character of Issa lives and spends the first stretch of season four staging a community block party to honor. It’s a series about friendships and how these friendships are defined and changed by this community.
Just watching Issa, Kelly, Molly (Yvonne Orji), and Tiffany (Amanda Seales) out in the world having fun is extra poignant, almost like a fantasy. Sitting outside with a pitcher of margaritas and some chips and salsa and laughing with friends, “sounds like heaven right now and we took that shit for granted,” Rae says.
But the show has never been pure escapism. The realities of the struggle, the torture of dating, the complexities of friendship, and the barriers to happiness are always present, more firmly rooted than ever this season as Issa’s professional success causes a rift in her relationship with Molly. The escalating tension is as devastating to watch as the breakup of any fan-favorite romance on a TV series.
“I’ve never had my heart broken by a man, but I’ve had my heart broken by friends,” Rae says. You outgrow people. Friends go down certain paths. The people you surround yourself with in your twenties are the people from your literal surroundings: friends from school, from the neighborhood, carried over from growing up. In your thirties, you come into your own and assess the people around you, realizing that maybe you don’t need to maintain those relationships anymore. It’s painful, Rae says. “My female friendships have broken my heart to pieces.”
The scenes between Issa and Molly are the most dramatic that the show has ever produced, recalling tense friend showdowns—and creative high points—from previous HBO series like Girls and Sex and the City. (That argument between Carrie and Miranda on the street when she decides to go to Paris, my god…)
“Your breast-milk taster is a huge Sex and the City fan,” Rae says, referring to Rothwell, who is also a writer on the show, “so I’m sure that reference came up.” What was most important to her was making sure that the women on Insecure never came off as “frenemies,” like it seemed the characters on Girls were. “Between Issa and Molly, even with what’s going on, there’s a genuine love,” she says. “It feels real.”
What feels real could arguably be the root of this whole empire that Rae has built in the four years since Insecure premiered.
She spent her elementary-school years in Potomac, Maryland, where she noticed she was the only black kid in one of her classes. When classmates discovered her dad is from Senegal, they pummeled her with ignorant questions about whether it’s dirty there and if she knew how to ride elephants.
When she was in middle school, the family moved to Los Angeles, where, at a predominantly black school, she was on the receiving end of the opposite judgment. Her classmates called her “white girl.” To compensate, she performatively accentuated her blackness, adopting a certain kind of speech, purposefully doing bad in school, and pretending not to like pop music—Britney Spears! LFO! No Doubt!—that she secretly loved.
After a childhood of being told what isn’t black and what black people don’t do, she eventually realized that the way she is, however she is and whatever she does, is black.
“I’m always observing how people are observing me,” she told me when we first met four years ago before Insecure premiered. “That’s the nature of being socially anxious. That’s also the nature of being black.”
It’s an ethos that inspired The Misadventures of Awkward Black Girl, the web series that Rae launched on YouTube in 2011, and her 2015 New York Times-bestselling memoir. Her work got the attention of Larry Wilmore, who would go on to co-create Insecure with her.
“I sometimes say that my career has only made me more insecure,” she says. “That just comes from job security. With every new opportunity I get, I still feel like I need to prove myself to maintain.”
It may not come as a surprise that, given all of the projects and ventures she’s juggling, she’s concerned about longevity. When Insecure launched, there was a certain swagger. She created something. People liked it. She made it from a web series to HBO, and did it the way she wanted to. Now it’s a success, and there’s a different kind of pressure and anxiety.
“It’s just like, what else do you have? What more can you do? Can you offer different things?” she says. “I ask myself those questions all the time. Ultimately, I know it’ll come down to me beyond the entertainment industry. You know, the show... that’s cute, and all that. But who else are you? So those questions have been plaguing me.” Her voice adopting a sing-song, joke-y cadence, she concludes, “And I blame Insecure!”
Blame aside, Insecure and all the work Rae put in to expand her reach in the industry means that she is now a force. She is a black woman in a position of power. She is in the position to not just hold the door open for other black women, but stage the party for them to come to. With A Black Lady Sketch Show as just one example, her focus has intensified on what she can do to bring people up with her.
“I think about that every day, and that is part of what I hope my legacy will be,” she says. “It also relieves pressure from me. One of the burdens that I feel is that burden of representation. I don’t want that pressure, and no one should have that pressure. Especially knowing that there are so many gifted storytellers who just aren’t getting that chance.”
She went viral after the 2017 Emmys for declaring in a red carpet interview, “I’m rooting for everybody black!” But it’s more than a fun soundbite. She is systemically, institutionally doing that.
“It’s the action version of it, because it’s just like, yeah, you can be on the sidelines and be like, ‘I hope you succeed girl!’” she says. “But if you have the platform and you have the means, then you can actually help them succeed.”
There’s a scene in the new season of Insecure that, the more we talk, seems emblematic of who Rae is now. The character Issa is enjoying more success professionally than she’s had in her life. She’s working harder than ever before, and it’s paying off. But after killing it at work, she goes back to her apartment and cooks a quesadilla in the microwave. The meal is sad. Real sad.
It’s not hard to extrapolate the real-world parallel, the life that art’s imitating here. Issa Rae is sitting on top of a Hollywood empire, but she’s still the Awkward Black Girl, going home at night and microwaving a sad-as-hell quesadilla for herself.
“But it would be vegan cheese, because she’s lactose intolerant,” Rae says. Did a microwaved quesadilla really just get even more depressing? “It really is,” she says, cracking up. “The cheese doesn’t even melt.”