Director Roger Ross Williams Always Roots for the Underdog

The first word that comes to mind when looking at Roger Ross Williams' filmography is prolific. The filmmaker, who made history in 2010 as the first Black director to win an Academy Award with his short documentary, Music for Prudence, has built an expansive body of work comprised largely of documentaries known for their beauty and compassion. Still, this may be his most career-defining year yet.

Earlier in 2023, Williams released Love to Love You, Donna Summer, an HBO documentary about the life and career of the disco queen, and directed episodes of Hulu's The 1619 Project. But this fall brings a true showcase for Williams: his first narrative feature, Cassandro, which stars Gael García Bernal as the gay luchador superstar Saúl Armendáriz, debuted in theaters on Sept. 15 and arrives on Prime Video on Sept. 22. His comprehensive documentary series, The Super Models, about the rise of Naomi Campbell, Cindy Crawford, Linda Evangelista, and Christy Turlington, hits Apple TV+ on Sept. 20. And on Nov. 15, his ambitious documentary feature adaptation of Ibram X. Kendi's book, Stamped From the Beginning: The Definitive History of Racist Ideas in America, comes to Netflix.

While Williams' work this year may seem to span a wide range of topics, from fashion to lucha libre, he says that there's a common thread that runs through his entire filmography.

"I love telling inspirational stories, stories of people where the odds were against them," he told TIME in a phone interview.

Ahead of his projects' releases this month, TIME caught up with Williams to talk about how he keeps his energy with so many balls in the air, being mentored by Robert Redford, and why he always roots for the underdog.

TIME: You've had quite the year. I got exhausted just looking at all of your projects.

Williams: It has been quite the year, but I can't afford to be exhausted—I have to just be excited by all these opportunities because I'm lucky to have these opportunities.

Your projects this year range from a Donna Summer documentary to your first narrative feature, Cassandro, about a gay luchador. What drew you to each of them?

I love telling inspirational stories, stories of people where the odds were against them, like the odds were against me as a young person, but who still went on to win an Oscar and to have this career. The odds were against Donna Summer, this young girl from Boston who grew up in this really poor, religious community. The odds were against these four young teenage girls who weren't handed their success, they fought hard and earned it. And the odds were against Cassandro, someone who conquered the world of lucha libre, a masculine world, on his own terms as an out gay man. Even my past films, like Life, Animated about the challenges of autism—all of these connect to the themes in my own life. My mother was a maid, she worked in a fraternity, cleaning the toilets. And I worked right alongside her as a little boy. So that's what drives me.

How do you keep up your energy? Do you ever get overwhelmed working on so many projects?

Right now, since everything is coming out at the same time—which is partly because of the pandemic—it seems like I did everything at once, but these were all a long time in the making. I'm also someone who never stops working—even when I'm sleeping, I'm thinking about work. But I balance it out. I live in the Catskill Mountains and I have a farm that I garden. My secret is that I build stone-laid stone walls. I'm a wall builder! That's very meditative.

How do you stay inspired while working on these long-term projects?

I run a production company called One Story Up, which gives opportunities to BIPOC filmmakers, opportunities that I never had. No one called me after I won the Oscar. No one was banging down my door. I still had to fight hard to get my first doc feature made, God Loves Uganda. So I'm inspired by the young, incredible creators that are so enthusiastic and have such great ideas. I spent seven years as governor of the doc branch of the Academy of Motion Pictures. When I walked into that room, I thought, 'I am not going to let this opportunity pass by without opening the doors for others like me.'

What also keeps me going is that we have to correct all this injustice not only in the larger world, but in our in our documentary community. It's why I made Stamped From the Beginning. I can't escape from the realities of being a Black man in America, so I'm going to talk about those realities. I am constantly exploring the realities of my existence as a gay man and a Black man and if I don't explore them, then who is?

Cassandro is your first narrative feature. What was it like for you to move away from documentary and into narrative? What were the challenges or unexpected joys?

It was scary. But tackling and running headfirst into your fears is a good thing, especially creatively. Cassandro started as a short documentary, but my biggest fear was actors. How do I talk to an actor? That's something I didn't know. So I did the Sundance screenwriting lab and then the directors lab, where Robert Redford was my advisor and he gave me great advice. He told me, 'Lean into your documentary skill set. What do you do with documentary?' I was like, 'Well, I make my subject feel safe and comfortable with telling their truth and their story.' And then he said, 'Well, that's exactly what you're doing with actors.' Once he said that, I realized that it really was the same. I'll always make documentaries, but I love that in a scripted film, everything in the frame tells a story. You get to create that, from the color of the lampshade to the painting on the wall. I can't control that in the documentary. That is so exciting to me because the possibilities are endless.

And why did you choose the story of Cassandro to be your narrative feature debut?

When I met the real Cassandro, I fell in love with him. There's no more inspiring underdog story than the story of Cassandro, a poor gay Mexican kid who decides to tackle a machismo world and becomes the star of it on his own terms. When I was shooting the documentary, I was in Juárez, Mexico, one of the most dangerous cities in the world, and in the lucha libre arena Gloria Gaynor's "I Will Survive" comes on and the whole audience starts singing it. Then Cassandro comes out in full drag, kissing babies, making his way to the stage in his long train and people are loving it, they're cheering for him. I started to cry. I said to myself, 'I want to tell this empowering story of a gay man because I want to see empowering stories about the LGBT+ community, not depressing stories.' His was more than I could ask for.

What was it like creating the film with the real Cassandro?

I wrote this with my editor from Life, Animated, David Teague, who spent a lot of time with the real Cassandro, and we really absorbed his life. Sadly, two weeks before we started shooting, the real Cassandro had a stroke and it paralyzed half his body and he couldn't speak. But one moment that stands out is when he visited the set when we were filming this really beautiful scene between him and his mother in the swimming pool. He came to set with his father and just wept. By far, the most powerful moment was when when I showed the film to Cassandro, in El Paso, in a beautiful theater for an audience of one. I watched him watch the movie and he was cheering and crying. And when he does this big moment, a stage dive, he stood up and raised his arms and mimicked the actions on the screen. And it was one of the most powerful screening experiences of my life because the real Cassandro was finally getting his due in the world.

With The Super Models, these are women whose visages have been so familiar to us for so many years. Was there anything new that you learned about them while directing this series?

I learned a lot about these women individually, but I'm really learned a lot about fashion. Runway models and [advertising] campaign models were totally separate, but they changed this as they rose to the top of fashion and then surpassed fashion to become culture icons. I also didn't understand the level of artistry and work that went into creating these stories. That doesn't happen anymore. Everything now is very fast and on Instagram, everyone can be a supermodel now. But these were the original influencers. They became a phenomenon because it was the merging of all of these things—Hollywood, the music industry, art and fashion, MTV. It was a perfect storm and it will never happen again. Change is good, but you need to know how this started.

What was your relationship to these women? Did they mean anything to you at the height of their fame?

Oh my god, I grew up with these women. As an NYU student working at the Palladium in the Michael Todd room, which was the VIP room, they were everywhere! They defined everything. I jumped at the opportunity to tell this story because they were such a part of my own story, my life in New York and growing up. It was exciting to be able to get to know them and to tell their stories—imagine hanging out with Naomi and Cindy and Christy and Linda. It's also fun as a documentarian to drop into this world. Plus I love fashion; early in my career, I actually covered fashion for CNN.

There is a lot of vulnerability, from Linda Evangelista talking about having cancer to Naomi Campbell opening up about the racism she faced in the industry. How did you build trust so they felt comfortable sharing these deeply personal stories?

It was really important to just hang out before we had cameras, to just go to dinner and get to know each of them. Larissa Bills, the co-director, and I would just spend time with each of them. That's how you build trust, right? You don't run in there with a camera and say, 'O.K., let's go.' And then by the time the cameras roll, they're comfortable to open up. Both of the stories you mentioned were incredibly emotional, and I was crying right along with them. We cried through the whole thing, it was like a therapy session.

The series gives the supermodels the chance to tell their stories on their terms. When you think about Naomi, for instance, she was reduced to just the phone throwing incident for many years in the media and mischaracterized as aggressive in what we would call now misogynoir. Your series gives us a lot to think about about how we talked about them.

Isn't interesting when we explore the real ways sexism and racism work in the world? These women were ready to talk. They were ready to tell their own stories from their perspective and it's about time. Isn't it time to empower women to tell their own stories? We filmed for seven hours and they were still going—they could have gone on and on because it was like they could finally open up and let it all out in a way that was powerful and shed light on the choices they made. That's what I live for as a documentarian.

Stamped From the Beginning is based on Ibram X. Kendi's nonfiction book of the same name. What was the journey like to adapt it?

When George Floyd happened in America and there was a racial reckoning, the number one book on the New York Times bestseller list was How to Be an Antiracist. I was blown away by the protests all across America and every small community, even upstate New York and in the tiny, all-white farming town where I live, they were protesting, they have Black Lives Matter signs. I was moved to tears and knew I had to explore that. Further down on the NYT bestseller lists was Stamped From the Beginning, and when I read that book, it broke down the history of racist ideas in a way I have never seen or experienced before, even internalized racism that I had against Black people myself as a Black American.

I didn't have the resources to option the book myself, so I called my good friends at Netflix and we said, 'Let's do this together.' I wanted to do it as a tight, 90-minute film because I wanted people to go into the theater or or sit down and watch it at home and be transformed. I wanted it to be accessible, to show how it relates to their lives today. And I want it to feel pop cultural because pop culture is how America disseminates racist ideas. Racism is embedded in our psyche. It destroys our culture and it hurts everyone. I wanted to use every tool in my toolkit to tell a really powerful story.

You only use Black women as expert sources in this. Why did you feel this was important to do in a documentary about the origins of anti-Blackness in the U.S?

With experts, so often they're white male historians. But when I started to look at this work, there was a pattern—there were so many Black women who were doing this work at Stanford and Yale, and Harvard and Howard. I asked some of the contributors [why they think this pattern has emerged] and they said, 'Because we can't turn away from it, this is our experience as Americans, so we make this our life's work,' which I found to be really powerful.

Also, Black women have always been documenting, whether it was Harriet Jacobs, Phyllis Wheatley, or Ida B. Wells. They were documenting and fighting [racism] just like in the past election, where Black women came to the rescue and saved America, in my opinion. Black women are often on the front lines fighting these battles, quietly and strongly. So I wanted to put Black women front and center where they belong in telling the stories of racist ideas in America. I want to give them their due and respect the scholarship and the work that these women have done.

What was it like working with Ibram X. Kendi to adapt his book?

I worked very closely with with Ibram X. Kendi. It's his scholarship. It's his life's work and he's a very important voice in this. He was an executive producer and he was involved in the whole thing, but the great thing about working with Dr. Kendi is that he respected me as a filmmaker and he let me translate his work into almost a pop culture way of telling the story. I love when a collaborator, as brilliant as Dr. Kendi can really understand that I'm talking in a different medium, and let me do the thing that I do—there's a mutual respect between Dr. Kendi and myself. I watched him at [The Toronto International Film Festival], when there was a standing ovation after the film and another after the Q+A and he had tears in his eyes because when he first tried to publish it, every single publisher turned him down before he got a small obscure publisher to do it. And look where it is now. Look where he is now. This was a gift to him and I was so happy to hand him this gift because he deserves it. He's a genius.