Lena Waithe on Hollywood Lessons Learned and Lifting Up Long-Ignored Talent

Lena Waithe has no use for gatekeepers. As the multihyphenate’s profile has firmly ascended since winning an Emmy for outstanding comedy writing on Master of None in 2017, the only thing that’s grown more than her television, film and streaming slate is the list of people who turn to her for guidance. Drop her a DM, and someday you might find yourself writing on one of her shows.

“I want to hear from people,” insists the writer, producer and actor, who founded Hillman Grad Productions in 2015. “My mission is to provide a space for people to grow, while making work that people can look at and say, ‘That broke a barrier.’ ”

With four series on the air (BET’s Boomerang and Twenties, Showtime’s The Chi and Quibi’s You Ain’t Got These), the films Queen & Slim and The 40-Year-Old Version, and a rich overall deal at Amazon Studios (where she has one series on the way and another in the works), at the age of 36, Waithe is a wunderkind compared to her closest peers — all at least a decade older, most of them white men. But she’d rather not be an anomaly — and she won’t be, if any individuals among the 100-plus women, POC and queer people currently enrolled in Hillman Grad’s mentorship lab follow her path.

“Lena once told me she’d always known she was going to win an Emmy; she just didn’t know it would be so early,” says Hillman Grad president of TV and film Rishi Rajani. “She wants to keep earning that award every single day and to do that by bringing other people up with her.”

Waithe, THR‘s TV Producer of the Year, acknowledges that giving (and getting) a big break is not always easy. One afternoon in early July, she spoke about lessons learned from The Chi‘s behind-the-scenes troubles, the semiautobiographical Twenties‘ frustrating road to a green light and how she’s chosen to engage in Hollywood’s reckoning for long ignoring Black talent.

Twenties put Jonica T. Gibbs, a masculine-presenting gay woman, at the top of the call sheet — a first for TV. Where do you think audiences are at in terms of queer representation on TV?

People have these ideas of what a gay woman looks like. There’s a chance I may fit into a stereotype of what a lesbian is because I’m a little more masculine-presenting. What I found in getting feedback on Twenties is that people didn’t expect for her character Hattie to be so silly and warm. Because of how she presents, they think she’ll be more aggressive — not listening to Whitney Houston while watching YouTube videos.

That said, the bisexual community still doesn’t have a ton of representation on television. There are still people whom we haven’t explored — people who identify as asexual, nonbinary, gender queer, trans. It’s important that people of a queer experience help tell those stories. Sometimes people ask me, “Hey, Lena, so you gay. I want to be educated about the trans community.” Well, you should speak to a person who is of the trans experience. Just because we fall under the same LGBTQIA+ umbrella doesn’t mean that I can educate you about every single letter.

It’s hard to imagine a character like Hattie on TV six years ago, when you wrote her. Is that why it had such a long road to the air?

I just wanted to write about my experience being in Los Angeles and having two straight best friends. There’s this idea that all queer people only hang out with queer people.

It hopped around a lot.

Hulu originally put it to development. It didn’t go. The pilot you see was shot and paid for by TBS. When I jumped to Boomerang at BET, Scott Mills said, “If TBS doesn’t do Twenties, we want it.” I said, “TBS ain’t that dumb, but thanks for the heads-up.” Sure enough, Time Warner had the merger. Kevin Reilly, who everybody said was going to have thoughts, called and said, “I do not have a single note for you on this pilot, but we can’t do it because of this merger.” I couldn’t get off the phone fast enough ’cause I knew I had a bird in the hand.

How did it evolve over those five years?

If you go back to the pilot presentation, the bones of it never changed. What ultimately happened is that I became a public figure. I got cast on Master of None. Because of that, I got Ready Player One. I won an Emmy. And then I was on the cover of Vanity Fair. I remember saying, “If somebody ever asks me on the red carpet what do I want to do next, I’m going to always say Twenties.” I wrote Twenties before The Chi. The Chi just happened to go first.

Why do you think that is?

It was an easier sell. It was gritty, it was dark, it was Black. But I remember, with The Chi‘s character of Brandon [Jason Mitchell], I was like, “He’s a Black boy with a dream.” It was hard to have that conversation. For some reason, it just felt foreign [to executives]. That’s no one’s fault. I don’t think anyone was trying to be racist. They just didn’t have the understanding. That’s the reckoning that’s happening right now. Black people have always had hopes and dreams. And I think that has been very difficult sometimes for white execs to understand and to allow us the space to write stories about that. I remember being so frustrated on those calls. I was like, “What is so hard to understand?”

How have calls like that changed for you?

The truth is, the notes process changes the higher up you go. Now I have to trust myself even more and talk to the people around me. I need to have checks and balances. Otherwise, you’ll put stuff out that’s just for you. (Laughs.)

Twenties was renewed, but do you worry about it finding a bigger audience?

I knew it would be a challenge having the show on BET in terms of getting an audience. BET is not known for their scripted programming. What [CBS chief creative officer and Showtime Networks CEO] David Nevins did for us, overseeing all of Viacom, was put Twenties on Showtime linear. That’s huge because there are people who watch Showtime and don’t even know where BET is on their cable dial.

One of your lawyers, Nina Shaw, wrote in THR about so often being the only Black person in the room. What does the rest of your team look like?

What any artist wants is the strongest team with the most access. You’re more successful when you have a team that thinks outside of the box but also a team that has friends in high places. Oftentimes those people aren’t people of color, or women. But I do think that’s changing. My team looks like a Benetton ad, but I’m not successful unless they are fucking phenomenal. And they are.

What needs to happen is not just for talent to demand, “Oh, you need to have an inclusive team.” It’s about the industry supporting Black and brown people coming up who want to be agents or managers and teaching them how to be the best in the business. Some of that comes from the hustle, but a lot of it is education. Sometimes you have to be told, “Don’t work in that mail room, do that one,” or “Oh, you don’t need to meet this person. Have lunch with this woman.” It’s chess.

You told Charlamagne tha God in a 2019 interview that you can’t trust anybody to do your job but yourself. How do you reconcile that impulse when so much of your job is delegating?

It’s tough. Everybody I hire isn’t going to be the right fit. All I can do is recognize that they’re not the right fit, make a change and ask for grace to course-correct. I have to take risks because I like giving people opportunities. The Chi was my first show. I needed some space to fall down and to not get everything right. But I learned so much from those mistakes. I think I’m in a better position to hire people.

What did you learn from the way the Jason Mitchell misconduct claims were handled and the departures that followed? [Mitchell was fired from the show after being accused of misconduct; co-star Tiffany Boone was released from the series upon her request, and season two showrunner Ayanna Floyd Davis departed.]

The way the show is being run now is how I would have wanted it to run since day one. When the foundation is broken, it takes a lot more time and energy to fix it. We had a very rocky foundation. I think that’s acknowledged among everyone. Time’s Up didn’t exist when the show started. The #MeToo movement hadn’t taken center stage. I didn’t have the language. I didn’t have the resources. There were times I felt powerless. Now that I am empowered and I have learned some lessons, I know how to make sure that the show feels representative of who I am. I put that show on my back this season. Make no mistake. I am always going to embrace a fucking challenge. It makes me a better mentor. I don’t mind giving it to people real because The Chi has really … man, it’s done almost taken me out a couple times.

I believe it was the same interview about Jason where you said you didn’t have the power to fire anybody. Do you have that power now?

Only in my company. With TV shows, I don’t write the checks. If I’m not signing your check, I don’t have the power to fire anyone. I have to go to the studio or network and say, “This is what I would like to happen.” If they don’t do what I ask, I have the right to walk away if I feel strongly. But I’ve gotten to a place where it’s more of a partnership, and, especially now, everybody is more inclined to listen.

The showrunner in the first season of The Chi, Elwood Reid, was white. Do you think you’re at a place in your career to ensure that the showrunner on a project you are producing, if it’s a show with a Black point of view, is also Black?

Yes, that’s always my preference. Luckily, I found that it is not as hard a conversation now as it was maybe three or four years ago. Networks and studios don’t want to be the place that a Black or a person of color says, “I was forced to have a white showrunner on my show.” Even though people did think that it was weird to have a white guy as a showrunner on [The Chi], it wasn’t. Now it is a little taboo. It goes back to Black writers not getting promoted quickly enough. Sometimes the studio comes back at you and says, “Well, they don’t have enough experience.” I want a Black person, and they can learn on the job. Often a Black person and a white person have been in the business for the same amount of time, but the white person is at EP level and the Black person is still a supervising producer.

Look at the résumé Prentice Penny had to build before he became a “showrunner” on Insecure.

Scrubs, Happy Endings, Brooklyn Nine-Nine … Shoutout to Prentice Penny. When I was an assistant at Girlfriends, he was like a lower-level writer. I was in New York, filming Master of None season one, and he texted me and he was like, “Yo, can you put in a good word for me with Issa Rae?” Hell, yeah. Mara [Brock Akil] had, too. It’s just been a joy to watch Issa and Prentice grow together.

You appear as yourself in an episode of Kenya Barris’ #BlackAF, in which you’re afraid to criticize a Black filmmaker’s movie. What is your relationship with film and TV criticism?

With Queen & Slim, I really stepped into that conversation. A number of Black reviewers were like, “Queen & Slim is fine, it’s not great.” It was important for me to amplify their voices, to embrace them even if they weren’t embracing my art in that moment. We’re Black artists — we do care what Black people think — but I’ve got to amplify them whether they love it or hate it. I really liked what Kenya was trying to say about Black artists not wanting to criticize other Black artists in public. And I think a big reason for that is because we still don’t have the same amount of art as our white counterparts. I like what Issa said: “I’m rooting for everybody Black.”

We’re seeing a lot of virtue signaling in Hollywood now. You’ve pitched mandates. Is that the realest action we should be taking to address systemic racism in this town?

Integration had to be enforced. If it wasn’t, we would still be in a segregated country. We need our own form of integration laws in this town. I was talking to someone who suggested that if your writers room isn’t inclusive, you’re fined or it’s taken out of your budget. It should feel taboo to be on a set that is not inclusive. If you are at a board meeting at a major network or a studio, and it’s not inclusive, you should feel uncomfortable. Until that is the feeling, we won’t make any change. The reason I’m pitching mandates, hitting people in their pockets, is because I know that’s what matters the most to people in this town. Money is power.

Interview edited for length and clarity.

This story first appeared in the July 31 issue of The Hollywood Reporter magazine. Click here to subscribe.