Natasha Rothwell: A New Queen of Comedy

Natasha Rothwell: A New Queen of Comedy

Natasha Rothwell needs to come up with a plausible “industry age” to represent how long she’s supposedly been on this Earth. She’s lived in Los Angeles, the land of lies and plastic, for as long as she’s written and starred in Insecure—almost three years—but she hasn’t yet learned what an industry age (a fake number that’s less than one’s real age) means.

After a light bout of rain in L.A., on a Wednesday in July, we meet for lunch at the Commissary, a restaurant trapped in a greenhouse, garnished with fiddle leaf figs and palm trees. Dozens of overhead hanging plants make the whole place look like a botanist’s Shangri-La.

When I ask Rothwell how old she is, she immediately tells me her real age (“I’m 37!”), which I find endearing, given how often the famous safeguard such information. Rebel Wilson took her alleged age fudging all the way to court, and Jessica Chastain once said, “I will never say my age because I’m an actress, and I want to play different ages.” (Hollywood favors the young and virile.)

Rothwell is now considering this (play along here). “What is that? What should I say?” she wonders, when I ask if she’s ever used an industry age. I suggest “33-ish.” She’s dressed in all-black—a head wrap and a t-shirt that reads “F*cking Vote”—and a no-makeup look that makes her seem not a day over “33.”

So it’s settled. “Put that in the interview,” she says. “‘She said, now that she knows what industry age is, she’s now 33 forever.’”

Not too long ago, hardly anyone knew Rothwell’s name, let alone her age. Before she was Kelli on Insecure, she was living in downtown Brooklyn, in one of the city’s claustrophobic studios. When Saturday Night Live was desperate to cast a black woman in 2015, she auditioned. The feature spot went to Sasheer Zamata, and Rothwell’s consolation was a job writing for SNL.

Being one of the institution’s few black writers (she refers to SNL as “a passport stamp”) helped her book a Netflix sketch series (The Characters) and a meeting with HBO programming exec Amy Gravitt, who recommended her for the show Issa Rae had in development about black women living and fucking up love in L.A.

Rothwell, a fan of Issa Rae’s web series The Misadventures of Awkward Black Girl, interviewed with Rae via Skype from her Brooklyn apartment.

“I pushed all my shit in a corner, and I made one corner nice and fancy. I was dressed professional from the waist up, and I had like pajama pants on, like, let me just sell myself,” Rothwell remembers.

She was instantly hired and left for L.A.

She was one of the first writers interviewed for the show. “I remember cracking up reading her script, ‘Worth the Weight,’ and then her personality and intelligence and sense of humor shone through the interview,” Rae tells Jezebel via email. “She’s very much about the small things and moments that make people tick and she’s also very sensitive to people. She’s very in tune emotionally, and very self-aware. I feel like those things are important when you’re writing a show about regular people.”

“Everyone has that real friend where you’re like, I hate you so much but thank you,” says Rothwell.

When Insecure premiered in 2016, it was heralded as the first big network show since Girlfriends to center around black women, at a time when the rest of television was struggling to find black friends. The show’s rarity is both a blessing and curse in terms of fandom. Discussions about each episode and characters’ bad decisions tend to evolve into gender wars, debates about its imperfections, and memes on black Twitter, where Insecure has replaced Scandal and Empire as the subject of water cooler talk online. Fans even launched a petition to bring back actor Jay Ellis’s character Lawrence (who’s absent from Season 3), along with the site

That passion is proof of concept. Insecure has existed not just as a topic of debate, but as a beacon of representation, proof that giving black creators space to put black people on TV is plain smart and lucrative. These awkward, attractive people serve as proxies for our friends. So when Issa (Issa Dee on the show) abandons her boyfriend Lawrence, the nice guy who works at Best Buy, to cheat and play around with Daniel in Season 1, it’s an affront. When Lawrence fucks up and toys with the emotions of the woman he’s casually dating, Tasha, in Season 2 (and gets called out as a “fuccboi”), it’s visceral. When Issa’s best friend Molly (Yvonne Orji) stops seeing an amazing hot guy because he had a sexual experience with a man in college, group chats ignite. In Season 2, Molly subsequently sleeps with her old friend Dro (Sarunas J. Jackson), who’s in an open relationship, and we wanna yell at her or, at the least, send her an angry text.

Of course, there’s a Kelli in every group, the friend who’s randomly blunt and funny beyond what the moment calls for. In the Season 1 finale, after Issa, Molly, and their friend Tiffany (Amanda Seales) sing happy birthday to Kelli at a club, Kelli blows out a candle and quips, “Y’all know I wished for dick!”

“Everyone has that real friend where you’re like, I hate you so much but thank you,” says Rothwell.

The emotional attachment we had to Kelli after just one season led to Rothwell being promoted to series regular, in addition to writer and coproducer. For Season 2, she co-wrote, along with Ben Cory Jones, all the episodes for Due North, the ridiculous drama-within-the-drama about a slave owner (played by Scott Foley) and a slave (Regina Hall) that gave us one of the best memes in history: actor Michael Jai White screaming, “I hate slavery!

Even when Rothwell’s not the center of attention, she’s a central force, which applies to her film career as well. In 2018’s Love, Simon, a coming-of-age story about a teen’s coming out, Rothwell plays the curt drama teacher Ms. Albright. A week after our interview in L.A., she lands a role many actors would triple-murder for, in the upcoming Wonder Woman 1984 sequel with Gal Gadot and Chris Pine. She’s also in the middle of writing her first studio feature, Bridal Recall, and developing her own comedy series as part of a deal with HBO.

Natasha Rothwell in Season 3 of Insecure Screenshot:HBO

It’s immediately apparent how she got all these jobs. In our hour-long conversation, she speaks with purpose, focus, and convincing platitudes, often in PowerPoint voice: “I’m excited for the opportunity to really take risks, and so I’m swinging for the fences,” she says. She’s both professional and warm but keeps it business and has the ability to throw you off guard with her humor.

Issa Rae recalls a recurring bit Rothwell did in the writer’s room, where she would pretend to answer the office phone and be fired: “If she thought she pitched a bad joke, she’d pick up the phone and say something like, ‘Hello? Yeah, they found out I’m not funny. Book a flight home.’ Or if we laughed hard at something she pitched, she’d be like, ‘Hello? I’m staying. They like me.’”

Leading up to the first season, Rae shared a personal story in the room for an intended dinner party episode. Another writer, Ben Dougan, wrote the episode, which never aired, but the script is what led to the formation of Kelli. About four months into writing, Rae and showrunner Prentice Penny knew they wanted Rothwell as their Kelli.

“I told myself, in between the hiatus of being hired for the show, ‘I may go back to New York…’” she says. “But I found out during the writers’ room that I was cast. I was like, I guess I live here now.”

The first time Rothwell wrote something that made someone laugh was in middle school when she crafted a series of limericks for a writing class portfolio. “I remember my teacher pulled me aside and was like, ‘Hilarious!’ I got that feedback and was like, oh this is fun!” In high school, she wrote something more serious: a monologue from the perspective of a young girl on the phone with her father in prison. “It was her expressing how she’s been let down,” says Rothwell. “I think that gravity necessitates levity, and levity necessitates gravity. I love dramatic acting and comedic performing and I really struggled with that in college because when I graduated, I wanted to tear my heart out.”

I softly bellow, “Stelllla!!!” in response. “Stelllla!!” Rothwell repeats.

Before transferring to the University of Maryland, where she got a full scholarship and graduated with a theater degree, she spent a year at Ithaca College as a journalism major. Her parents, born and raised in Philadelphia, had the most serious jobs imaginable, saving lives. Her dad worked in the Air Force, which meant their family lived everywhere from Illinois, to the area of northern Florida that inspired Floribama Shore, to Incirlik, Turkey. (Rothwell was born in Wichita, Kansas.) Her mom worked in comprehensive cancer and hematology. After her first semester of college, Rothwell made the tough decision to tell her parents she wanted to do the most dreadful thing and become an actor, which saves lives in a different way.

“I remember watching Nell [CARTER] and just seeing myself reflected, Like, she’s beautiful, funny, and smart, and she looks a little like me.”

“I had concocted this whole after-school special story of like, they’re keeping me from the arts! I have to do this quote-unquote legitimate career path,” she says. It’s in these moments that she enters true theater mode. “I came home at Christmas and I was sobbing, like, ‘I don’t wanna do this! I wanna be an actor!’ My parents were like, ‘We knew that’s what you wanted to do… We were really confused by the journalism thing.’”

Her heart was close to improv, as were her TV idols: comedic geniuses like Carol Burnett (specifically Mama’s Family), Vicki Lawrence, Tracey Ullman (“She really hit a chord with me—the ability to transform and play multiple characters”), and Nell Carter. “I remember watching Nell and just seeing myself reflected,” says Rothwell. “Like, she’s beautiful, funny, and smart, and she looks a little like me.”

Unfortunately but fortunately, Rothwell kept being cast in comedies and kept getting frustrated, until her mentor told her she was avoiding the inevitable—she was, in fact, funny. “I was just frustrated that I wasn’t seen in a different way. And he really helped me understand that if you’re going to be taken seriously as an actress, you can bring your dramatic chops to combat,” she says. “I feel like one of the best parts of playing Kelli is that she’s dead-ass serious about what she’s saying. She plays it with the drama, but it’s funny because it’s heightened circumstances, and she’s earnest about something that’s kind of silly. But the earnest part is what’s funny.”

Rothwell had to accept her lot in life as a comedian. She became part of a comedy troupe in college (Erasable Inc.) and performed improv in and around Washington, D.C. and New York, some of it with the veritable Upright Citizens Brigade. UCB was not unlike the comedy troupe she was in with her siblings growing up (she’s the second oldest of four). For fun, they would play “Make Me Laugh,” where one of them would sit in a chair while the others took turns playing court jester. “We weren’t like the Jackson 5, but we cut up all the time. If I can get them to laugh, that is such a win for me ’cause they’ve been tired of me for,” she exaggerates, leaning into the recorder (my iPhone), “thirty-three years.”

I tell her the game me and my sisters played was “School” (where we would write on a chalkboard and pretend to be teachers; Rothwell played that, too), and that I grew up a middle child, for which she gently ribs me. “So you’re just claiming that status. You’re like,” she feigns a baritone prison voice, “‘I’m middle.’”

Post-college, Rothwell worked as a theater artist on contract gigs, going from D.C. to Tokyo (for a year) but got tired of having “13 different schedules and bopping all around the city,” she says. “When I was in Tokyo, my sister was like, ‘Hey, one of my friends is starting a charter school and they’re looking for a drama teacher.”

Rothwell became a full-time teacher for the newly opened charter school in the Bronx, KIPP, where she worked for four years. “That was my first way of being like,” she says, “proximity to passion will make my bread job a lot easier.” Later she landed on Insecure.

Issa Rae and Natasha Rothwell in Season 3 of Insecure Screenshot:HBO

At lunch, a family of probable tourists is playing what sounds like a rousing game of ping-pong behind us. Rothwell has ordered sparkling water and a veggie appetizer. One of the vintage plates here features a black-and-white image of an old maid pouring water into a basin while a cow stares at her and another cow drinks from the basin. (I can’t explain this.) The drink menu is written on a worn, brown envelope that has a man’s name and address on it, which Rothwell, like I did, mistakes for actual mail. Insecure shot a scene here early in Season 1, between Issa and Molly, which is why I picked it as a spot to meet and feel their aura.

When Rothwell asks the waiter for a straw, I tease, “Do you know there’s like a straw thing happening now?”—the straw ban. It leads not to comedy but a serious talk about how the ban might affect the disabled community. “I feel like in these situations, I welcome the opportunity to become more woke about things that I’m not ordinarily,” Rothwell says, in earnest.

Of all the controversial topics on Insecure last season, it was an episode about blowjobs—more affectionately, “the blowjob episode”—that drew the most intense reaction online. In Season 2’s “Hella Blows,” while attending a sex convention, Issa and her friends get into a divisive discussion about giving head. “Who puts a condom on when you giving a blowjob? That’s like eating a popsicle with the wrapper on,” Kelli opines. Both Kelli and Issa (who complains that she has “big teeth”) dislike the process. (“I have to really fuck with you to put your dick in my mouth,” Issa says.) Molly just wants reciprocity. Tiffany, the haughty one, chimes in, “I just don’t understand black women and their hang-ups about oral sex.” Issa equates blowjobs with black men seeing black women as “disposable.”

Later in the episode, Issa gives in and grants Daniel a BJ that ends with a, uh, facial, as blowjobs sometimes do. She gets upset and storms out. The episode received so much criticism that the show’s writers had to defend it in a BuzzFeed article. On Vulture, in a piece titled “Why Insecure’s Blow-Job Scene Felt Out of Step With the Typically Radical Show,” Angelica Jade Bastién called the episode regressive for advancing the idea that black women don’t “do” blowjobs. In a video posted on YouTube, writer Kimberly Foster gave the show more latitude, arguing that the episode raised an important question about “the modern sexual mores of black women.”

Obviously, the varying opinions of the blowjob episode reflect a richness of blowjob thoughts in the writer’s room.

As a viewer, the episode felt tonally reductive for Insecure, but the feedback was also a sign of the show hitting a sweet spot between criticism and resonance. Not since the iconic blowjob bib appearance on Empire had we seen such strong reaction from fans around the act of a blowjob on a television show.

“A lot of the criticism has been: ‘This is not my experience. I’m a black person. Y’all are the only show that looks like this. I don’t see myself,’” says Rothwell, one of eight black women in Insecure’s writer’s room, out of 11 people total. “While that episode, people were like, ‘That’s not my truth,’ somewhere that’s a truth. We all know of people having conversations, especially under this current administration, that are very antiquated, where it’s like, didn’t we already have this conversation?

Obviously, the varying opinions of the blowjob episode reflect a richness of blowjob thoughts in the writer’s room. The show is relatable not just because it’s representative, but often because it’s not.

“Everything you see that comes to fruition comes out of passionate discussions about real life, real feelings, real emotions,” says Rothwell. “We’re one of the only millennial black shows on television that features women, that explores their lives with them as the focus. They’re not magical maids. We’re not coming through as just being the sidekick. These are lead women telling stories about the community, that we don’t get to see. And yet, it’s still not everyone’s story. So my hope is that people are pushed to tell those stories that are meaningful.” She adds, “Tell the version of the story where everybody’s just dropping to their knees giving head! Write that show. I’ma watch it.”

“Tell the version of the story where everybody’s just dropping to their knees giving head! Write that show. I’ma watch it.”

Ultimately, the core of the show is the tight friendships and what it takes to maintain them. The first episode of Season 3 introduces Issa in transition, both personally (she’s sleeping on Daniel’s couch; things are tense) and professionally (she needs a new job; things are tense). Molly, fresh from a self-care vacation, is focused on reclaiming her time.

Like Rothwell, my first contact with Issa Rae was through Awkward Black Girl, a show that not only assuaged my feelings of constant social anxiety but, in hindsight, was the digital precursor to the prevalence of color on TV now. Insecure, a natural extension of that series, leaves a similar impression on a broader audience. The drama hits so close to home that when a seemingly less realistic thing happens (the BJ refusal), it’s easy to be taken out of the action.

Our primal beefs with these characters is part of what fuels the story and keeps us watching to see, for example, what will happen when Molly, who’s fucking with Dro, who’s in a supposed open relationship, finally sees that she’s using him as a temporary salve for her innermost fears and desires.

“Whatever he has going on with [him and] Molly, it hasn’t been said if his wife knows what’s going on or they’ve had that conversation, like, ‘Hey, this is what’s happening,’” I tell Rothwell.

“We didn’t see that conversation happen, but he said it happened,” she says.

“Right, he said it happened.”

(I’m not really angry.)

“Mmm, you don’t trust him,” Rothwell infers, in the tone of a therapist. “I think it’s very interesting tackling non-monogamy in black culture. It’s very taboo, so that reaction I think comes from that, where it’s like, ‘I don’t trust him no way!’ Though a scene between Dro and Molly in the Season 3 premiere seems to support that his wife knows about them, I’m still skeptical.

“I’m a fan, so I feel like an audience member when I watch with the audience, too,” says Rothwell. “I have moments where I’m like, ‘Girl, no! Why!’ I love that about the show. There’s no decision where you’re just like, how did that happen? We can see how at the end of the second season, there’s a knock on Daniel’s door and, you know, I’ve showed up on those doorsteps. I know what it’s like where you just feel like it feels familiar.”

In that same episode, Issa and her friends search for Kelli at the Long Beach Marathon and Half-Marathon, which Kelli ran after training for months. They find her at the medical tent wrapped in a sheet of tinfoil from the waist down. The sight alone is enough, but Rothwell’s expression of exhaustion further sells the moment. “I got my period,” Kelli says, to which Molly wonders, “Why didn’t you just put in a tampon and keep it moving?” Kelli reasons, “Well, it got me before I could get it. I got to mile nine and the red wedding hit, just killed my draws. Dead.” Issa tries and fails to stifle laughter.

When Girl’s Trip had the biggest opening weekend for a comedy last summer, its success reaffirmed a big point to the masses: black women can be funny across a spectrum. Insecure has in some way done its part as well to expand the image of black women in comedy. “People think of black women comedians, but it’s only one version,” says Rothwell. “We can go all the way from Sommore to hard-hitting to more nuanced, subtle performances and it’s still comedy. Like, Issa’s still comedy. That, to me, has been the thesis of Insecure: we can do more than what we’ve been given.”

“We can do more than what we’ve been given.”

Rothwell points out that since the number of television platforms is at a peak, the Oz heads in Hollywood aren’t just looking for non-white material but any content to fill the gaps. “Do you know how much content we’ve consumed that is terrible? Because people are allowed to fail publicly?” she says, meaning white people. Rothwell says she’s taken meetings with executives who tell her they now have the budget to take a risk on, dare I say, a black show.

“I think that so much of the choices that black people make are [because] we can’t slip, not once, and we have to be perfect, work twice as hard to get half as much. But my hope is that the opportunity and the number of platforms will allow black people to start taking risks. We can do all that kind of amazing, crazy art if we’re given permission to fail.”

As she talks about risks and failing, she makes a rogue motion with her arms that sends the straw from her drink glass flying. Perhaps a sign that the straw ban is valid. She apologizes.

Rothwell’s schedule is so packed with Wonder Woman, Bridal Recall, and her HBO comedy that on her end, there’s a low probability of failure. “I’m doing shit that scares me,” she says, which includes writing and starring in her own show. “My character in the show definitely explores one’s journey in life to figure out who she is, what she wants, and that includes her love life and trying to find someone to be with, but doing that in a way that’s surprising and unexpected,” she explains. “If it’s on brand for me, that comedy will have gravity and levity.” It’s promising, the idea that we’re just beginning to see her comedic range and she’s only 33.

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