Lena Waithe Forges Her Own Mainstream

When you don’t see your stories onscreen, you “stay the course,” Waithe says. “Don’t let anyone deter you”

What’s the common thread between an ensemble drama in downtown Chicago, a queer coming-of-age comedy in modern-day Hollywood, a Black “Bonnie and Clyde,” a docuseries about sneaker culture, and a searingly intimate marriage story? The answer, of course, is Lena Waithe, the creative force behind Showtime’s “The Chi,” BET’s “Twenties,” the award-winning film “Queen & Slim,” Quibi’s “You Ain’t Got These,” and Netflix’s “Master of None,” respectively. 

Ask Waithe herself what connects such disparate projects, and you get a glimpse at the creative instincts of a true Hollywood multihyphenate: The variety of the work is part of the point. “I don’t want to be known for doing one thing,” Waithe tells Backstage. “I’m definitely someone that colors outside the lines; I don’t live inside a box. And I’m always trying to do something that feels honest and new and different and interesting, and in many different forms.”

Chatting via webcam, Waithe alternates between speaking at a rapid clip, idea upon idea spilling out of her, and listening intently, as if with her whole being. You get the sense that those qualities lend themselves well to someone who’s used to leading a writers’ room, or jumping from pitch meeting to press interview to AT&T commercial voiceover gig. Waithe is doing all that and more, particularly in the COVID-19 era, when “you actually can become more productive by being at home,” she says with a laugh. “I can have five meetings in the span of literally an afternoon. There are two writers’ rooms up right now that I can jump [into] quickly right after this Zoom!”

Born in Chicago and having aimed “to be considered one of the greats in television” since childhood, Waithe transferred her job at Blockbuster to a Los Angeles location soon after graduating from Columbia College Chicago. Years of juggling survival gigs with low-paying internships at networks and studios eventually led to assisting an executive producer on a sitcom (“Girlfriends”); writing for a procedural (“Bones”); producing shorts and viral videos; and working with the likes of Gina Prince-Bythewood, Queen Latifah, and Justin Simien. The latter collaboration spawned the 2014 indie hit “Dear White People”—around the time Waithe booked her first acting gigs on “The Comeback” and then Aziz Ansari’s “Master of None,” despite having no on-camera aspirations.

But being ready for opportunity, in whatever form it takes, has been central to her mission from the jump. “I think sometimes people prefer artists to be inside a box, because it’s like, ‘OK, you do this one thing really well. Always do that.’ Sometimes that works, you know? Sometimes it makes sense. But for me, it can be suffocating. It’s like telling Mary J. Blige, ‘Only sing happy love songs.’ ”

That refusal to be pigeonholed is more than just a means of survival or a creative mission statement; it can pay the bills. In 2017, Waithe became the first Black woman to win a writing Emmy for “Master of None” Season 2’s “Thanksgiving,” an episode inspired by her own coming-out story. Again, she could have stayed in one lane, just playing the character of Denise. “I had no plans of ever writing on the show, actually, because I really wanted to keep it separate,” she says. She was focused on her first blockbuster feature role in Steven Spielberg’s “Ready Player One” when Ansari insisted on the two of them churning out the episode together in three days.

“People always say, ‘What’s the highlight of your career?’ ” reflects Waithe. “It’s not winning the Emmy. It’s the smoothness with which Aziz and I wrote that episode in London over the course of a weekend. And it was because I had been writing, watching so much TV, doing so much studying and listening and learning, that when the time came… To me, it’s the equivalent of somebody passing to [Michael] Jordan. He’s got a few seconds on the shot and he has to clear it. It’s not the shot-making. It’s all the things he has to do to be in position to make the shot, period. That’s the win.”

Waithe’s big break also mirrors two interconnected entertainment industry trends of the past few years: more and more up-and-coming artists embracing the term “multihyphenate,” and Hollywood’s mainstream expanding (slowly but surely) to invest in stories from creators who happen to be female, Black, or queer. Waithe, who is all of the above, remains at the forefront of the fight for diversity both on- and off-camera—a growing movement built on “shepherding and encouraging community,” as she says. 

“I’m part of a creative community with Issa Rae and Donald Glover and Justin Simien and Terence Nance and Michaela Coel,” she adds. “I knew all these cats coming up.” It’s no coincidence that her production house, Hillman Grad Productions (a nod to the fictitious college in “A Different World,” a favorite sitcom of Waithe’s), features a community-based Mentorship Lab designed to forge the kind of professional partnerships that led to those creatives’ varied successes. It’s a blueprint for creating more inclusive spaces in a more equitable industry—proof that a rising tide can lift all boats.

“For me, now, the mission is to bring as many people as I can with me,” Waithe says. “I’m not just fighting for myself; I’m fighting for those that haven’t been heard yet. And they deserve to be heard.”

Under the auspices of Hillman Grad, with Waithe as CEO and Rishi Rajani as president, “The Chi” premiered in 2018 and is now four seasons strong; the drama’s newest installment premiered May 23. Additionally, projects previously stuck in development, like BET comedies “Boomerang” (a sequel series to the 1992 Eddie Murphy and Halle Berry film, co-produced by Berry) and “Twenties” (a semiautobiographical retelling of Waithe’s introduction to Hollywood) got their greenlights. “Queen & Slim” followed a year later, helmed by “Thanksgiving” director Melina Matsoukas, and Waithe has since produced Radha Blank’s award-winning indie “The Forty-Year-Old Version,” Little Marvin’s Amazon Prime horror anthology “Them,” and more.

“The way I make my work, it’s all gut-based,” she says of her approach to each creative venture. “In the process, my question is always: What’s honest? How do I want to tell this story?”

That first question is a guiding principle not just for Waithe, but all of her closest collaborators. And honesty doesn’t necessarily mean true-to-life accuracy. Take, for instance, the new, spinoff-esque season of “Master of None,” titled in full, “Master of None Presents Moments in Love.” Featuring Waithe’s Denise and Naomi Ackie as her wife, Alicia, and taking place mostly in a picturesque yet isolated country home, the five episodes chart the blissful highs and crushing lows of a marriage complicated by, among other things, Alicia’s attempts to have a child. 

“Lena is so creative, so inventive, so honest,” Ackie tells Backstage. “I think when you’re making art, you have to be honest and upfront about how you feel about things. You have to be honest and upfront with what your boundaries are…. She managed to juggle being a producer, being a writer, being in it. Being invested in a story but having enough of an objective eye to look at it, to also be outside-in—it’s just super impressive.

“Outside of the fact that she’s funny as hell,” adds Ackie. “She’s a genius, you know? I mean, she’s got it all.”

Unlike the “Thanksgiving” episode, Waithe, Ansari, and co-creator Alan Yang eschewed autobiography, drawing inspiration from French romantic dramas; interviewing doctors, nurses, and women who have undergone in vitro fertilization; and passing scripts back and forth for years. “We really wanted it to feel honest”—there’s that word again—“and real,” says Waithe. “Aziz and I have that in common, where we don’t want to do it unless it’s really going to be something special.”

The relentlessly long, single-take shots of “Moments in Love” allowed the actors to exist naturally in such real circumstances, grounding the stakes in the profoundest intimacy. “It’s probably the most vulnerable acting I’ve done in my career,” Waithe says—an understatement, considering Denise and Alicia’s roller coaster of emotions and the chemistry between them. “A lot of it was me really centering myself, being still, and just not letting you see the machine work. Because it is; it’s working overtime!

“I do hope that audiences can see this is a part of my story as an artist,” she continues. “That I never was ashamed of anything, of who I am, of my body, of myself. And it may make some people uncomfortable. But I hope that it makes them less afraid of themselves, if it can.”

That’s where the second component of Waithe’s creative process—“How do I want to tell this story?”—comes in. It requires that fearless sense of purpose, that faith in a gut-based approach—or, as “Queen & Slim” star Jodie Turner-Smith puts it when describing Waithe, “assuredness.” 

“There is something so admirable about a person who moves with that kind of certainty about what they want to say,” says Turner-Smith. “I think, as a woman creating in this industry, operating in this business, there’s so much of that that you need. Because so often, people are going to question you and doubt you and undervalue you, just because you’re a woman—and also just because you’re Black.”

Speaking from one’s innermost voice also explains how Waithe navigates, for lack of a better term, the haters. “People can take all the swings and all the hits,” she says. “It doesn’t matter; I’ve already survived. There’s nothing anyone could throw at me.” 

Especially in today’s digital age, when celebrities live on social media, working in show business means dealing with those “wanting people in the public eye to be perfect all the time, even though that’s not possible,” says Waithe. And it’s exponentially more true for minority artists who are underrepresented in pop culture. “[There’s] this idea that, because I’m Black, because I’m queer, because I’m a woman, because I’m all those things, I have to be, like, pristine.

“This is a space that my white counterparts don’t sit in. Scorsese, Tarantino, my brother Spielberg, they don’t have to contend with that. So I now get to be an artist, but also have to make sure that I’m ‘a credit to my race,’ which Hattie McDaniel said so eloquently in her Oscar speech all those years ago.” As Waithe points out, many in the Black community did not believe that McDaniel was doing enough to combat stereotypes—that she should have refused her Academy Award–winning role of Mammy in “Gone With the Wind” and other maid characters. “But if she did not take those roles, what was she to do? To have a dream unfulfilled? And her doing that opened up the door for Halle Berry and Diahann Carroll and Queen Latifah and Viola Davis.”

Waithe has never been under any illusions that entering a predominantly male, white, straight industry, let alone shifting its mainstream like those women before her, would be simple. “The one that goes through the brick wall first is going to be battered and bruised. That’s just what comes with it. So, therefore, I will take that. I will carry that. I will be that. What other choice do I have?”

Can that kind of perseverance and assuredness be emulated? How could anyone adopt the unflappable attitude of someone who’s shown up at the Met Gala first in a revised rainbow Pride flag cape, then a “Black drag queens inventend [sic] camp” zoot suit?

“Stay the course,” answers Waithe with a shrug. And embrace the inevitability of failure on your way to success, she adds. “You learn more while you’re in the valley than you do on the mountaintop. You have a great view, but in the valley is when you have to figure out: OK, well, how do I get out of here? That’s what makes you stronger…. I’m always more drawn to those who make mistakes and figure out how to smooth it out versus those who never seem to trip. It’s like, we all are going to trip. Because that’s what connects us: our flaws, not our perfection.” 

Confidence comes from getting back up again after you fall; Jordan couldn’t make the shot without countless failed attempts during practice. That brings us to Waithe’s advice for early career artists: “Craft is first,” she says. “Craft, craft, craft. The business is always changing. The world is burning. If you know how to craft a really great story, if you know Final Draft inside and out—if you can do that, you will always eat.”

Waithe repeats the mantra: “Stay the course. Don’t let anyone deter you. Even if somebody doesn’t like it or thinks you’re wack, stay the course, because walking in your purpose is not supposed to be easy. If it was, everybody else would do it.” 

Additional reporting by Matthew Nerber.

This story originally appeared in the June 10 issue of Backstage Magazine. Subscribe here.

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Photographed by Shayan Asgharnia on 05/12 in L.A.