Advertisement

Issa Rae's Uncompromising Comedy

When it's time for Issa Rae to become Issa Dee, the transformation starts around the eyes. They get more incredulous—as if in alarm at the sheer number of awkward moments a person can encounter in the span of a single scene, or an entire life. On the set of HBO's Insecure, which Rae co-created and stars in, she is confident: in charge. But then it's time for a new take, and the change into Rae's on-screen alter ego—slightly more hapless, significantly more broke—begins. The coat, sweatpants, and slippers she uses to stay warm on air-conditioned sets come off, the sense of competence that otherwise envelops her fades, and the eyes begin to search, somewhat desperately, for the solid ground of purpose that Issa Rae has, and Issa Dee most definitely does not.

Your coffee table could use some style. Click here to subscribe to GQ.

Today, on a blue white hazy afternoon, Insecure has taken over a nightclub in the Mid-City area of Los Angeles, a block south of the 10 freeway. Rae, who is 33 and grew up about four miles from here, in View Park-Windsor Hills, is scrupulous about representing the L.A. she knows. Over time, she's developed an unofficial rule about where Insecure does and does not shoot, and she avoids going north of the freeway if at all possible. “Growing up here, nobody lives in Hollywood. Nobody lives north of the 10. This is a blanket statement, but most of my friends from L.A. are black and they live south of the 10 or, like, along it, or Mid-City. That's the L.A. that I know, and that's the L.A. that I want to represent and portray.”

Rae had been on set for two weeks, shooting the show's third season, and the stress of managing a cast and crew of a hit show had begun to mount. In the fall, she was nominated for a Golden Globe, for the second time, for her work as an actress on the show. Last year, HBO gave Insecure its ultimate honor: a Sunday-night time slot right after Game of Thrones. Rae is often described as the first black woman to create and star in a premium-cable series—a compliment so specific that it tends to make her feel entirely misunderstood, if not insulted. (“I mean, who cares? I'm gonna be next to, what, Rosa Parks and Martin Luther King?”) It might be more accurate to say Rae is part of a vanguard of young creators making television in ways that television hasn't quite been made before—raunchier, realer, less beholden to the demands of a mass audience.

Insecure, which is about the lives of a handful of young black women and men in various stages of their careers (including: not really having careers), takes delight in the comedy of everyday existence: passive-aggressive co-workers (“Issa, what's ‘on fleek’ ”?), the advice of well-intentioned but slightly confused confidants (“You got to fuck a lot of frogs to get a good frog”), the adrenaline rush of doing the wrong thing. The show, built around the Issa character's friendships (most notably with a lawyer named Molly, played by Yvonne Orji) and romantic stumbles (often with her ex, Lawrence, played by Jay Ellis), depends less on any kind of linear plot and more on the types of confusing yet vivid encounters that pile up in one's 20s and 30s. (In the second season, Issa describes a recent sexual encounter as a “nebulous fuck.”)

Early on, the show worked a bit like a sitcom: jokes in search of a meaningful structure. But since those first few episodes, Rae and her collaborators have steadily raised the emotional stakes, to the point where HBO asked Rae whether they were still making a comedy. “I remember HBO seeing the first episode of the second season and being like, ‘Oh, my God, is our show dramatic?’ ” Rae recalls. This blurring of the line between antic heartbreak and heartbroken antics is the root of Insecure's appeal: It feels like life.

In the scene they were preparing to shoot, Issa reunites with an on-and-off love interest, Daniel, at a nightclub. It was the kind of subtle scene Insecure excels at: a casual moment turned excruciating. The script called for the two of them to enter the club and then share a moment of inadvertent physical closeness when Daniel leans over to talk in Issa's ear—as she registers, with increasing panic, their sudden proximity. In the club, as extras dance silently in the background, they run the scene a few times—in each take, Rae would work out new, silent inflections of discomfort and desire before stammering a reply and escaping to the bar.

Rae regards the actual acting she does on the show as, mostly, a means to an end—“I can take it or leave it, to be honest,” she says. When she first had the idea for the predecessor to Insecure, the web series The Misadventures of Awkward Black Girl, “I had another friend of mine in mind, and then she couldn't do it. So I was like, ‘I'm running out of time. I'm just gonna do it myself.’ ” But Rae turned out to be a gifted comic actress—under pressure, as her characters often are, she talks faster and faster, as if to get her words up to cover-fire velocity—and now she's so strongly identified with her creation that fans regularly scold Rae on social media for choices her character has made. “In naming the character Issa and in going out and about and minding my business in the world, people still, no matter what you do, are gonna associate,” Rae says ruefully. “It's you. You know?”

Finally, in a close-up shot, Rae fumbles her line. The episode's director, Pete Chatmon, yells cut. “Can we do that again?” A deliberate beat. “And get it right?”

“I got it right like 72 times, bitch!” Rae replies. Even the extras start laughing.


After the crew breaks for a late lunch, Rae begins the work of transforming back into herself. An assistant arrives with her sweatpants and slippers. Standing on the sidewalk outside the club, the haze of the character still dissipating, she puts on the slippers and then attempts to put on the sweatpants before realizing her mistake. Rae looks down at her feet and sighs.

“I did this wrong,” she says.

Rae sometimes refers to herself as shy, and in person she tends to bridge the gap by being both inquisitive and bracingly direct. At one point, talking about the history of television and Insecure's place in it, she mentions Sex and the City, a show that, to my now regret, I have not seen.

“You never. Watched. Sex and the City?”

No.

“Why? First of all, how old were you when it came out?”

I'm 35 now.

“So you were around my age when it came out. I didn't watch it until college, and it came out I think when I was in high school. 'Cause it was around the same time as The Sopranos, right? Were you watching The Sopranos when you were in high school?”

I went back and saw that.

“Okay, so...” Rae looks at me patiently.

Maybe there's some chauvinism in the fact that I went back and watched one and not the other.

“Totally. I'm glad you recognized that.”

Rae's willingness to speak her mind, paired with her on-screen exhibitionism, is what makes Insecure work. But this quality can also come at a cost: The source of her creativity, in many ways, is her genuine discomfort with being the center of attention. “I do feel like people expect me to be entertaining,” Rae says. “And I'm not. I'm not an entertaining person. I don't put on for anybody. I think about someone like Tiffany Haddish, who's just naturally entertaining, who always has a story. And that's just not my lane. I'm always gonna be the shy one.” Orji says that when she and Rae first met, she was surprised by how much Rae was like the character she'd played on Awkward Black Girl. “She really does give off an awkward energy,” Orji says. “She really is shy. She has a hard out. She has limits. She really is this person. It's not an act.”

Rae's first series, Dorm Diaries, was a satire about black life at Stanford more or less as she was living it at the time—the misunderstandings and missed connections of college-era existence. After she posted it on Facebook, people responded immediately, and for a moment it seemed like an interested network might even make it into a show. When that didn't happen, Rae created Awkward Black Girl. She was working at a corporate nonprofit job, and the show was about the daily indignities of office life and dating in Los Angeles. The series, which she posted on YouTube in 2011, was watched by millions of viewers.

“What most surprised me was that the audience wasn’t 90 percent black.”

In the aftermath of her newfound success, Rae signed a book contract. At the time, she says, she thought: “This is great for the process! This is great promotion! I'm getting paid to write! Like, all those things. All those things that 25-, 26-year-old me is like, Yes, this is the goal.” In the 2015 book The Misadventures of Awkward Black Girl, she wrote, in jarring detail, about her father's unfaithfulness in his marriage to her mother and about her childhood habit of adopting the “white-girl name” Jennifer to flirt with strangers online. Today she looks back on the book and cringes at the level of autobiography it contains. “Just being such a private person, going back, I wouldn't ever write about my stuff,” Rae says. “There's no doubt that it worked, but books live forever.

In television's so-called golden age—The Wire, The Sopranos, Mad Men—the difficult men who created the difficult men on-screen were able to stay behind the curtain; viewers tended to care about Tony Soprano, not David Chase. But television—especially vaguely comedic television—in the era of personal branding is a very different animal. It's not a coincidence that many of the most successful creators of the past several years—Rae, Girls' Lena Dunham, Atlanta’s Donald Glover, Broad City’s Ilana Glazer and Abbi Jacobson—have had to not just write or direct but also star in their own shows, often telling stories that could plausibly belong to them in real life. This is a recipe for success. But it's also the strategy that drove some of their predecessors, like Dave Chappelle, to near madness: If you mine your life too closely, and too publicly, for laughs, you risk having nothing left when the gambit pays off.

“I only want to make my presence felt when I feel like it's necessary,” Rae says in her trailer. “And so much of that is such a hard balance, especially when the narrative is about getting noticed and getting attention for a specific product. And in that way, yeah, I want the eyes to be on what the product is”—meaning Insecure. “But after a while, you become the product.”


Rae often says that an inspiration for creating Insecure was watching the sitcoms she grew up on, shows with predominantly black casts like Living Single and A Different World, disappear from television—a void that no one seemed inclined to fill. Growing up in Los Angeles, where her father, a doctor from Senegal, had a practice in Inglewood, Rae would frequently recognize her own neighborhood in movies like Love and Basketball and on shows like Girlfriends. Then that stuff just vanished. “The takeaway was ‘Agh, black people are so dope. Where are they at on TV right now? Now I want my own version.’ ”

But television shows in the 1990s were made for massive audiences that often numbered in the tens of millions. “If you're selling advertising, your sole metric of success is ‘Were the ratings high or low?’ ” says Casey Bloys, HBO's head of programming. Modern comedies like Insecure work on a different model, one that necessarily comes with the proliferation of cable channels and online outlets: fewer people, more passion. “Even something like Girls,” Rae says, by way of comparison, “which I hate being compared to, but I thought it was a huge ratings hit because of the way people talked about it.” In reality, as Rae found out, Girls was watched by 800,000 to a million people—about the same number of people who watch Insecure. But “people were talking about it. Whether you loved it or you hated it, you were talking about it.”

Rae says because of this she doesn't worry much about her ratings. Neither does HBO, though Bloys says the network is very happy with them: “The show got amazing reviews, both in the first season and the second season. And you can't quantify it, necessarily, but there is buzz around her and the other actors on the show. So it is doing its job as far as I'm concerned.” Rae is more interested in the makeup of her audience. “I think what most surprised me was that the audience wasn't 90 percent black,” she says. “I think only 30 to 40 percent of the audience are black people. But I'm like, okay, HBO isn't accessible to everyone. Like, I didn't have HBO. I used my friend's password until the show got picked up.”

Watch:

Issa Rae: Don’t Be “That Guy”

See the video.

In 2012, after Awkward Black Girl took off, Shonda Rimes helped Rae pitch ABC on a show called I Hate L.A. Dudes. ABC bought the show, but the series fell apart in development, as the network picked Rae's script apart with a constant barrage of notes and changes. It was a formative experience. “I was a mess,” Rae says now. “I was just like, Yeah, I have this shot, but I don't want to fuck it up, so I'm just gonna listen to what everybody says. And I just became like fucking clay for people to mold. The Shonda process was, like, the best shit that happened to me, because it gave me confidence to feel like, ‘Oh, I can do this.’ And I feel like ABC took the confidence away.” Rae emerged from the experience determined never to compromise in that way again: “Like, I need to know what the fuck I want to say before I say yes to any opportunity. I need to have a clearer point of view and clear voice.” When HBO called, the following year, and asked Rae if she had any ideas for a show, she finally felt like she knew the answer.

A lot of television creators circa 2018, such as Orange Is the New Black's Jenji Kohan and Atlanta's Donald Glover, will talk proudly about having pitched one show and then making a completely different one—a conventional premise made thrillingly unconventional in its execution. But, Rae says, with Insecure, “there was no Trojan horse necessary.” If anything, she says, HBO pushed her the other way: toward the tragicomic stories about her life and friendships that she was relating to them in development meetings for the show. Insecure is frankly profane, and also black in a way that doesn't bother explaining itself—a natural outgrowth, perhaps, of the relationship between Rae and her showrunner, Prentice Penny, a constant presence on the show's set and in its writers' room. “We grew up a block over from each other in the same neighborhood,” Penny says. “We currently live in Inglewood a block away from each other. We're both very L.A. There were things we didn't have to explain to each other.”

“In order to eventually succeed, you have to bomb.… And I feel like I’m still fearful because I haven’t publicly bombed yet, in terms of my career.”

As a result, even the show's white writers and producers—who are in the minority among the mostly black staff—are occasionally mystified by references in the scripts. But they also understand that's how it should be. (“We were on the set last week having lunch,” Rae recalls, by way of example, “and Yvonne asked me, like, ‘Oh, what's that seasoning that some of y'all be putting on mangoes?’ And I was like, ‘Lucas.’ And our white writer Ben pulled me aside. He was like, ‘That's what “Lucas on mangoes” means?’ There's a line in the show where somebody says, ‘We go back like Lucas on mangoes.’ And I was like, ‘That was in season one, and you've let three seasons go by without asking?’ ”) HBO is hands-off in this respect, too. “There are a lot of references that I don't get in the show,” Bloys says. “And that's fine. I can figure it out. But we don't typically ask for clarification notes for people who may not know. Because I think for a show like this to be successful, authenticity is always important.”

Insecure acts as if it already has the audience it wants, and in doing so it has helped broaden the definition of what that audience might be. In the show's second season, there's a scene in which Issa visits a neighbor for what she hopes will be a romantic encounter. Shortly after she arrives, he puts on Gossip Girl.

“Yeah, white people,” he says, nodding at the screen.

“There are so many of them,” she says amiably.

“It's good to see them doing they thing,” he says—as pithy a summary of why anybody watches anything as you'll get.

Insecure, more than most shows on TV, literalizes and plays with the experience of being placed in someone else's head—in an oft-repeated formal conceit, Rae's character will turn to the camera, usually in the form of a bathroom mirror, or a daydream, and just say to the audience what she can't say in life. This has always been Rae's gift as a writer: a deep sensitivity to what people share and what they don't. “I feel like I'm emotionally intuitive,” she says. “I sense things and observe certain things about people. I try to pay attention to clues as much as possible.” Part of the intention behind Insecure, for Rae, was to tell “a story about people of color in a different way...aligning it with the psyche and aligning with what this person is going through, so you just immediately get in and don't have to explain.”

Rae compares the relative freedom she has in making Insecure with ABC's Black-ish, which was recently in the news. After the show's creator, Kenya Barris, co-wrote and shot an episode that reportedly featured a debate about football players kneeling in response to police brutality, ABC and its parent company, Disney, declined to air the episode, citing “creative differences.” In response, Barris was said to be weighing an exit from his contract with the network. “That would infuriate me,” Rae says. “You know? Like, I'm out here telling the truth, and I'm telling my authentic experience, and you pride yourself on having this show that exposes the plight of a black family in the United States, and then you're censoring: No, not that. We don't want to see that part. The world isn't ready for that. America's not ready. That's crazy to me.... Kenya tries to couch so much in a family show, and get so much across, in a way that I really respect and admire. But a lot of the time it is just mired in the Disney, ABC of it all.”


When I next see Rae, it's in a bagel shop just down the street from the office she keeps in Manhattan Beach, in a complex of office parks and coffee shops just south of the airport. She arrives wearing a Spider-Man hoodie pulled tight around her face, gold wire-rimmed glasses, and an air of weary resolve, like an athlete going into overtime at the end of a long game. “It feels like I'm being tested in a really crazy way,” she says, not bothering to hide her stress. “It's nothing I can really get into. It's like third-season problems along with, like, just life shit. As a creative, I never imagined that I'd be a boss, too.”

Rae has a rare day off from shooting Insecure, and she is spending it trying to fit in everything she'd forced to the margins of her life: a doctor's appointment, this interview, a trip to the writers' room to finish the season finale of the show. She has a script for another show she's developing, called Sweet Life, about the lives of the young and rich kids in her childhood neighborhood, Windsor Hills, due tomorrow—“And do I have it? No”—and various other projects she's producing for HBO: Him or Her, about “the dating life of a bisexual black man and the distinctly different worlds and relationships he finds himself in,” with the writer Travon Free; and an untitled drama written by The Turner House author Angela Flournoy. She was reading scripts for other shows and for movie parts she was being offered in between takes on the Insecure set. Today she is teetering under the weight of it all. “A lot going on that I didn't anticipate,” she says, sighing.

Being the face of Insecure has led to opportunities she probably never would have had if she were merely a writer or director: a recent cameo in the video for Drake's “Nice for What,” parts in a couple of upcoming films, meetings with whomever she cared to have meetings with. But it also left her with nowhere to hide. “The failure is yours,” she says. “It is yoursss-uh.

Is the prospect of failure still scary to you, now that you've had some success?

“How?”

You're on the third season of a popular show—I'd describe that as success.

“That could go to shit,” Rae says. “This could be the worst season we've ever had. And then what? Then people are all of a sudden like, ‘Oh, okay.’ Then the calls stop. It's like stand-up comedy: In order to eventually succeed, you have to bomb. That's what every comedian says—that's when the fear goes away. And I feel like I'm still fearful because I haven't publicly bombed yet, in terms of my career. Yeah, Insecure is successful now, but where's my bomb coming? Where are my Will Smith bombs coming? Where, where is that happening?”

Will Smith is fine!

“He went through a period when he was depressed, when three or four of his movies in a row weren't number one at the box office. So for him that was terrible. And now he's talking about, ‘You gotta fail, you gotta fail.’ ” She pauses. “And I don't want to make Instagram speeches about failing. I don't.”

Outside the window, the late-afternoon light signals that it's time for her to again go back to the office. As she stands up to leave, a woman at the next table over looks closely at what little part of Rae's face is visible under her hoodie.

“You did Insecure, right?”

“I did,” Rae says cautiously.

“I love your show.”

“Thank you,” Rae says. And then she leaves, to go make more of it.

Zach Baron is GQ’s staff writer.

This story originally appeared in the June 2018 with the title "Issa Rae Is So Fresh."


Watch:

Behind Issa Rae’s Fresh GQ Photo Shoot

See the video.