Cover Story
April 2018 Issue

Lena Waithe Is Changing the Game

Garnering accolades and a passionate following for her work on breakout shows such as Master of None and The Chi—and appearing in Steven Spielberg’s new film, Ready Player One—Lena Waithe is taking over screens big and small. The star and creator opens up about influence and inspiration, from the Harlem Renaissance to Time’s Up.
Lena Waithe photographed in Los Angeles.
Lena Waithe, photographed in Los Angeles.Photograph by Annie Leibovitz; Portrait styled by Jessica Diehl.

In your life, if you’re lucky enough, you are born during a moment in time when the world is ready for the change you’re bringing. So all that’s left for you to do is your work. If you are a child named Lena Waithe, you find your passion on the television screen, or, as you call it, your Third Parent. Your mother, knowing that in front of the screen you’re safe from the streets of Chicago, allows you unlimited watching.The Cosby Show and A Different World bring you beautiful people, families you understand, and lots of laughter. And because when your grandmother watches with you she controls the remote, you watch old reruns of The Jeffersons, Good Times, All in the Family, and realize as you watch these people that this is what you have—words and characters and story. These are the tools these shows are giving you. So you lean into the screen. Already you know there isn’t a mirror the television is holding up to you; there isn’t a child like you on the screen. Not in the 1990s. Not yet. So you find your strength and a deep belief in yourself in the streets and family dinners of Chicago—a place you call home, a long way from your grandmother’s own Arkansas. You’re clear-eyed and queer from the womb, born as part of a larger narrative—that of the Great Migration. Already, there is resistance running through your veins. Already, at seven, you know your own dream. So you gather a posse around you. And in your 20s, you move to California, thirsty, eager, ready. Slowly, the bigger world begins to see you. We see you, Lena Waithe. We see you.

Lena Waithe, photographed in Los Angeles.

Photograph by Annie Leibovitz.

If you haven’t heard of Lena Waithe, check yourself for a pulse. She is disrupting the hell out of Hollywood. As the first black woman to nail an Emmy Award for Outstanding Writing for a Comedy Series, Lena—along with a crew of other black creatives—is sending a message to the world that Black Brilliance has arrived in Hollywood and has not come to play.

Lena and I sit down to dinner for the first time, at the Four Seasons in Beverly Hills. Having spent the past week in Utah for the Sundance Film Festival, both of us are beyond happy to be rid of our snow boots and winter coats. And because I’ve arrived at the restaurant a few minutes before Lena, I’ve had time to do what many of us do when we walk into spaces like this—count the Blacks. Now that Lena has joined me, there are two of us.

In this moment the shine is on Lena. She is all dapper and grace as she enters. Broad-shouldered and fast-walking, she flashes a smile at our hostess and emphasizes her please-and-thank-yous with our waitress. When she sits down across from me, she immediately removes her cap, and I smile, having grown up watching the boys and men around me get chastised for not removing their hats fast enough, for attempting to wear hats at the table, for even considering walking into someone else’s home or a restaurant with their heads covered. Lena’s locks are well oiled and tightly twisted, draping down past her shoulders—a femme contrast to the shaved sides of her head.

I begin to see that this is who Lena is: a woman coming at the world from many different places, quick-moving and fast-talking yet soft-spoken and thoughtful, cursing a mile a minute while bringing a new vibrancy to language. Relaxed yet ready. On the butch side of queer but with delicate edges. Star power with kindness. And it’s working.

“Here’s the irony of it all,” she says after the conversation gets going. “I don’t need an Emmy to tell me to go to work. I’ve beenworking. I’ve been writing, I’ve been developing, I’ve been putting pieces together and I’m bullets, you know what I’m saying?”

I do. On the critically acclaimed Netflix series Master of None, for which she won her Emmy, Lena, 33, also plays the role of Denise, a young lesbian and close friend of Aziz Ansari’s character, Dev. While Denise was originally written for a straight woman, who would eventually become a love interest of Dev’s, Waithe’s character has added a depth, humor, and black-girl queerness new to the screen. She’s wry, lovely, and lovable. And while Lena’s Denise seems to be handpicked from Lena’s life story, Waithe brings to this character something different. Denise is more reserved than Lena. It’s not so much an innocence but angles smoothed over, the product of a quieter past. Many of the people in my own queer world would have blinked past the show had it not been for Waithe’s character. For so many of us who have not seen an out Black lesbian front and center this way, her arrival is a small, long-awaited revelation. Her arrival is our arrival.

Photograph by Annie Leibovitz; Portrait styled by Jessica Diehl.

And then there’s the Showtime hit The Chi, created and executive-produced by Lena, which follows inter-related characters on Chicago’s South Side. With Common as an executive producer and Rick Famuyiwa directing, the show has been picked up for a second season. The credits keep on coming, though. Waithe produced the comedic dance film Step Sisters. She is the writer-producer of the recently green-lighted TBS television pilot Twenties, which is loosely based on her early years in Los Angeles and tells the stories of three black women making their way in Hollywood. And she appears this month in Steven Spielberg’s Ready Player One, which is adapted from Ernest Cline’s 2011 science-fiction novel, following contestants pitted against one another in a virtual-reality world.

When she’s not producing, acting, writing, or creating, Lena is working hard to pull more people of color and queer artists into film and television both through her role as co-chair of the Committee of Black Writers at the Writers Guild and through her work with aspiring writers via Franklin Leonard’s the Black List—a platform by which people can pay to get feedback on their material from established professionals.

But right now Lena is ordering an oyster appetizer, sitting back, and chatting with me about, among other things, our time at Sundance. Kindred is the vibe I’d put to this evening. Lena and I have not spent real time together before, but there’s a deep knowing between us. We talk about our families, our girlfriends, East Coast versus West Coast, and the movies that didn’t quite work at the festival.

Lena’s family, like mine, was similar to the fictional Cosbys—not in wealth, by any means, but in the way the young people on the show were expected to respect their elders. Separated by more than 20 years, we were both raised by our mothers and grandmothers. We both came out when we were young and have amazing women helping us to stay afloat: my partner is a physician; Lena’s fiancée, Alana Mayo, is the head of production and development for Michael B. Jordan’s media company. (Like me, Alana grew up a Jehovah’s Witness.) By age seven, we both knew what we wanted to be. We both started our lives in the Midwest—me in Ohio, Lena in Chicago. When our parents separated, our mothers returned to their mothers’ homes. My mother’s mantra was: Turn off the TV and pick up a book. But Lena, after coming home from school, was permitted as much television as she wanted.

“I was watching a lot of movies I shouldn’t have been watching,” Lena tells me, laughing. “Like Boyz N the Hood. Also a lot of rated-R shit. Jungle Fever. But that’s the joy of having a single mom. She was like, I can’t hover over you. Watch what you want. Just don’t repeat what you hear and don’t do what you see.”

When Lena was 12, her mother moved her and her sister to the suburbs: Evanston, just north of Chicago. “She was saving up and maybe a little bit wanted to get out of the South Side. Even though I was going to a good school [in the city], Turner-Drew, which was like an early magnet school which she found, because that’s the kind of shit she did.” Lena says this with true gratitude. “So half of that year I was still on the South Side and the other half I moved to Evanston and went to Chute Middle School. It was like a fuckin’ Benetton ad.”

At one point, Lena goes silent. It’s when I ask about her father. She tells me he died when she was 14. “He had substance-abuse issues, which my mom told me about later, but . . .”

Her voice trails off. Maybe another writer would have pushed her for more. But in that moment I only want to sit with her in the quiet, to muse, wordlessly, about the strength of mothers and grandmothers and the many levels to our survival.

Growing up, I leaned into books, finding small parts of myself in the writings of Mildred Taylor, Audre Lorde, Virginia Hamilton, and Walter Dean Myers. Lena, meanwhile, found her mentors on the screen in the comedy writing of Susan Fales-Hill (A Different World, Suddenly Susan), Yvette Lee Bowser (Living Single, Lush Life, Black-ish), and Mara Brock Akil (Moesha, Girlfriends, Being Mary Jane). “They didn’t get their shine,” she says of these early black women in comedy. “They were constantly banging on the doors.” In contrast, she says, “I rolled up and all I had to do was tip it and walk through.”

Somewhere over the course of the two decades between us, we both found the works of James Baldwin. His writing was as relevant in the early 2000s for Lena as it was for me in the 70s—indeed, as it was for the young queer black artists coming before us in the 50s and 60s.

And still, this evening, as Lena and I talk across the table, over her truffle pasta and Sprite, and my burger and Cabernet, a deep reverence comes over us. Here we are now because Baldwin was there then. And I think about the young people who ran to their screens to watch Lena’s Master of None episode in which her character came out to her mother. How social media blew up with her thank-you speech at the Emmys. (“I love you all and, last but certainly not least, my L.G.B.T.Q.I.A. family. . . . The things that make us different, those are our superpowers.”) How her work is part of a continuum of people doing their work.

“How has the Emmy changed me? It got me all these meetings that I go in and say I’m too busy to work with you—you should have hollered at me. You can take my call when I call you about this black queer writer over here who’s got a dope pilot, or this person over here who’s got really cool ideas, or this actress who’s really amazing but nobody’s seen her.”

Because we both know that, even as Hollywood’s doors are being shaken, there is still so much work left to be done.

Waithe takes in an old episode of The Mary Tyler Moore Show.

Photograph by Annie Leibovitz.

Lena came up as an assistant to director Gina Prince-Bythewood (Love & Basketball), whose father-in-law, an orthodontist, fixed my smile 30 years ago—just in keeping with Small Black World magic. Lena tells me she came to Hollywood in 2006 with no family, no friends, and no money. After working with Prince-Bythewood, she became a production assistant on Ava DuVernay’s scripted directorial debut, I Will Follow. “She would make the coffee,” DuVernay explains. “She would close the gate; she would take out the trash; she would run things from one part of the set to another.” Through it all, the director noticed real promise.

Now that Lena is catching major fire—at a time when TV show-runners and filmmakers of color, especially women of color, are getting the opportunity to tell their tales—there seems to be a sea change. Or am I being naïve? “Is this different than any other time?,” DuVernay asks me rhetorically. “It’s a good time, but it’s not the first good time we’ve had, and previous good times have not become That.” She reminds me that a similar moment existed in the 90s, thanks to filmmakers like Prince-Bythewood and Julie Dash, the first black woman to have a theatrical release, with her groundbreaking film, Daughters of the Dust,not to mention Kasi Lemmons’s Eve’s Bayou, and, on the queer side, Cheryl Dunye’s The Watermelon Woman. At that point and now in this one, DuVernay notes, you can easily count the black directors. It has been the same, she maintains, for women’s creative progress through the years. “We can look at other times in the history of art where it’s been the case where you’ve had a cluster or flurry of women who have been doing strong work that’s been recognized by the mainstream and feeling like it’s a moment, feeling like there’s a big culture shift. But, really, when you look at it and you’re sober about it, you’re talking about women that you can count on two hands—and this industry has many hands.”

Yes, she acknowledges, black artists are blowing up the screen, with everything from Kenya Barris’s Black-ish to Donald Glover’s Atlanta, to Issa Rae’s Insecure. But this isn’t yet “a moment,” DuVernay reminds me. The director of A Wrinkle in Time (budget: $100-million-plus) says, “If no other black woman makes a film more than $100 million past me for another 10 or 15 years, if no other woman wins an Emmy for writing, for the words that come out of their head, then we’re kidding ourselves that we’re in a moment that makes any difference other than momentary inspiration.”

Lena explores this terrain, too. “The hardest thing about being a black writer in this town is having to pitch your black story to white execs,” she says. “Also, most of the time when we go into rooms to pitch, there’s one token black executive that sometimes can be a friend and sometimes can be a foe. I wonder if they think it makes me more comfortable, if that makes me think that they’re a woke network or studio because they’ve got that one black exec. It feels patronizing. I’m not against a black exec. I want there to be more of them.”

For all that, Lena contends, “it was a symbolic moment when Moonlight literally took the Oscar out of La La Land’s hand. It is a symbolic moment when Issa Rae’s poster is bigger than Sarah Jessica Parker’s. Now the hands that used to pick cotton can pick the next box office. . . . See what I’m saying? There’s a shift that’s happening. There’s a transition of power. But we still aren’t in power.”

When I ask Lena if she thinks we’ll ever have our lesbian Moonlight, she is quick to tell me we’ve already had it. “Pariah,” she says, referring to Dee Rees’s stunningly rendered 2011 feature about a young black lesbian coming out. “I fuck with that movie really hard. I thought it was really beautiful.”

Waithe sits in L.A. traffic.

Photograph by Annie Leibovitz.

Waithe fixes her coif.

Photograph by Annie Leibovitz.

It is a few days earlier, on a cold night in January, following a blizzard. Sundance is in full swing and I’m watching Lena work magic in one of the hottest and most pumping rooms in Utah—a venue called the Blackhouse.

Co-founded by Brickson Diamond, in 2006, the Blackhouse Foundation came into being after the few black folks who’d been attending Sundance grew tired of seeing so few reflections of themselves on the Park City streets and of seeing so few black films. So Diamond, a graduate of Harvard Business School, along with two friends, Carol Ann Shine and Ryan Tarpley, created a place where their peers could gather to educate, network, and figure out how to break the white ceiling of Hollywood. During this year’s festival, the Blackhouse hosted panels and parties from 10 in the morning until midnight, Friday through Monday. Its impact is evident. In 2007 there were seven black films at Sundance. Come 2018, the count was closer to 40. “If you build it,” Diamond says, “they will come.”

Tonight the Blackhouse is hot, the drinks are being poured, the people are excited to be here, and the D.J. is dropping beats that are hard not to move to. Outside, a long line awaits entry to the main event: a discussion examining cinematic diversity and inclusion. In attendance: Radha Blank (Empire, She’s Gotta Have It), Jada Pinkett Smith, Poppy Hanks (whose production company, Macro, specializes in works by people of color and is the force behind Dee Rees’s Oscar-nominated Mudbound)—and Lena Waithe.

As a Sundance neophyte, I try to stand out of the way of a futile attempt to clear the dance floor and set up chairs for the panel. I hesitate to inform the D.J. that, in the history of black folks, no one has ever left the floor when a Prince song was playing. And now, not even two years after his death, Prince’s music in the room is a heartbreaking and sobering reminder that, as black creatives, we don’t have a lot of time to get the work done.

The room is already filled with beautiful people. A woman who worked on the costumes for Black Panther is one of the few who are able to negotiate heels tonight. Everything she is wearing, I want. Next to her, my friend Chris Myers is discussing the Sundance debut of Monster, a film based on a book by his father, Walter Dean Myers. Cards are exchanged, selfies are taken, bodies are pulled into long embraces. The crowded room, filled with everyone from crew to cast to producers, feels like a family reunion.

Nearly 100 years after the Harlem Renaissance—the African-American intellectual and artistic movement of the 1920s—I can feel in this pulsing room what it must have been like to sit among the likes of Zora Neale Hurston, Countee Cullen, Langston Hughes—people who were dreaming themselves and their work beyond the moment in which they were living. Tonight feels as energized and ready as that vibrant corner of Harlem must have felt a century ago. This new Black guard is no longer fighting for a seat at the table; they’re convening their own. And yet, while some call this surging West Coast energy “the Hollywood Renaissance,” I am with Ava DuVernay. We need to see how far past this now it goes, before we can own it.

When John Amos, the dad from Good Times, walks into the Blackhouse, the crowd parts. People whip out phones for selfies, which he graciously allows. For so many, Lena included, this is where the journey into black television began—when we first saw ourselves reflected back through the characters of J.J., Michael, and Thelma. As a young child, looking for mirrors of myself in episodes of The Brady Bunch and The Partridge Family, it wasn’t until shows like Good Times and The Jeffersons blued into our darkened living room that I could finally say, Yes, some part of that is me.

With the chairs set up and the music suspended for a while, Lena sits onstage alongside the other women. She pays homage to the creators of A Different World as her fellow panelists echo their agreement, tell her to say it, nod in memory and reverence. “We as artists can do whatever the fuck we want to do,” she urges the audience. “We just have to do it really, really well. . . . You have to write and develop and wait for the world to catch up to your art.”

Later, Justin Simien, creator of the Netflix comedy hit Dear White People, tells me that Lena has not only worked like mad but also “created systems, and now she’s got almost 100 mentees going to writing classes, and evaluating each other’s work.” In fact, she recently announced an initiative with the Black List that lets upstart writers submit scripts to be judged on a point scale. “Get an 8 or above,” Lena tweeted, “[and] my team will read your script.”

“She turns nobody away,” says Simien. The pair met at a writing workshop and became best friends. It is Waithe, he insists, who pushed him to take the leap and create Dear White People. “When Lena decides that something is true, it becomes true.”

Waithe and fiancée Alana Mayo in their kitchen, in Echo Park, California.

Photograph by Annie Leibovitz.

Lena and I meet for brunch, this time in West Hollywood. She sports her signature ensemble: hoodie, with a snapback logo cap. Today’s hat says, REBEL EIGHT. Another favorite is Chance the Rapper’s “3.” I ask her whom she likes to wear and she quickly spits out a list of queer and black designers. Sheila Rashid; Knoxxy’s brand, DVMN Pigeon; Nicole Wilson.

Lena considers her personal style her own mode of self-expression, irrespective of the circles she travels in, which, in professional Hollywood, tend to be largely white and, often, male. As much as anyone appreciates a compliment about their “look,” she says she doesn’t needit. “Being black and gay, having dreadlocks, having a certain kind of swag, and dressing the way I do,” she explains, she is sometimes told by certain well-meaning admirers or fashion wannabes, “ ‘That’s dope, you’re cool.’ I don’t feel validated by that. . . . I don’t want to be White. I don’t want to be straight. I don’t want to blend in. . . . I try to wear queer designers who happen to be brown and makin’ shit.”

I reach out to Common—who signed on as an executive producer of The Chi in 2015—for his read on Lena. “There’s no box you could put her in,” he says. “It’s not only [the fact that] I admire her, but I feel like I’m just somebody who sits and listens, looks at her work, and is like, ‘Man, this is really great writing!’ ” He points out the pure poetry of it, the humor, the deep honesty.

Steven Spielberg echoes this. When I speak to him, he says, simply, “I adore her.”

In Spielberg’s new film, Ready Player One, Lena’s character is part of a group that bands together to save a futuristic world. And while I know that sounds like every sci-fi movie ever made, this one is different. This one is No way, did he just . . . ? and Wait a minute . . . did that really . . . ? different. It’s hard to say more without spoiling the plot. When I attended a screening, I was beyond surprised to walk out of the theater already planning to return with my family, saddened only by the fact that once again it was the white straight people who found love. Lena’s acting chops, though, are on point here again. Spielberg says of her audition, “She was accessible at a glance. Her honesty was glaring. And she couldn’t hit a wrong note, because she found a way to be herself on-camera. I suddenly felt like I had hit the jackpot. The magic hadn’t walked into the room—until Lena did.”

Waithe’s collection of choice footwear.

Photograph by Annie Leibovitz.

A few days before Lena is scheduled to speak at the Essence Black Women in Hollywood ceremony, where she is being honored, our talk turns to her work as an activist and in the Time’s Up movement. As she reads out loud to me from her upcoming speech, her voice is a mixture of immense excitement and barely concealed fear: “Being born a gay Black female is not a revolutionary act. Being proud to be a gay Black female is.”

At the event, which takes place just before the Oscars, Lena talks about the importance of coming out in Hollywood—and explains it through her love for The Wizard of Oz. “There’s this moment in the movie,” she says, “when Dorothy’s presence interrupts the peace in Oz, which forces all the Munchkins to go run and hide. So Glinda the Good Witch tells them . . . to stop hiding. She tells them to come out: ‘Come out, wherever you are. Don’t be afraid.’ It’s interesting how things you hear as a kid take on a whole new meaning when you are an adult.” The day after her speech, pictures of her in a beautifully tailored gold paisley suit flood social media. The country is taking notice, sending love.

“I have a ton of mentees,” she tells me over the phone. “They’re all people of color. Some of them are poor. And I’m just trying to help them learn how to be great writers; and for those that have become really good writers, I help them get representation; and those that have representation, I want to help get them jobs. That to me is a form of activism. I was doing this before Time’s Up was created. I am doing it now. Activism is me paying for a writer to go to a television-writing class.”

It is during one of these conversations that I ask her about what happened with her friend and Master of None co-star, Aziz Ansari, who, in a controversial online article, was accused of sexual misconduct by a woman he once went on a date with. (Ansari stated that their sexual activity was consensual.) Lena gets quieter, more thoughtful. “At the end of the day,” Lena says, “what I would hope comes out of this is that we as a society . . . educate ourselves about what consent is—what it looks like, what it feels like, what it sounds like. I think there are both men and women who are still trying to figure it out. We need to be more attuned to each other, pay more attention to each other, in every scenario, and really make sure that, whatever it is we’re doing with someone else, they’re comfortable doing whatever that thing is, and that we’re doing it together. That’s just human kindness and decency.”

And then, a day or two later, we hop on the phone to scream about the success of Black Panther. We just have to. And Lena, being Lena, has already broken down the context of this moment. “You see history books—A.D. or B.C.?,” she asks. “I feel like the world felt one way before B.P. and will feel forever changed A.B.P. These execs are all looking around and saying to themselves, ‘Shit, we want a Black Panther; we want a movie where motherfuckers come out in droves and see it multiple times and buy out movie theaters.’ And because we also live in a town of copycats, there are going to be a lot of bad black superhero movies coming because everybody ain’t Ryan Coogler!”

Lena, naturally, comes back to the beginning, returning to the roots of her storytelling. “I used to watch TV with my grandmother a ton. I watched a lot of old [classic sitcom] TV. And it gave me an education in using your platform to protest, but without being preachy. And how you can use TV characters, fictitious characters, as a way to speak to who we are as a society.

Mayo and Waithe at home.

Photograph by Annie Leibovitz.

“I am tired of white folks telling my stories. We gotta tell our shit. Can’t no one tell a black story, particularly a queer story, the way I can, because I see the God in us. James Baldwin saw the God in us. Zora saw the God in us. When I’m looking for myself, I find myself in the pages of Baldwin.”

Then she adds, “I didn’t realize I was born to stand out as much as I do. But I’m grateful. Because the other black or brown queer kids are like, ‘Oh, we the shit.’ ” Lena flashes a huge smile, then shakes her head with wonder.