In 2010, Roger Ross Williams made history as the first Black director to win an Oscar. Perhaps more remarkably, he did so with his very first short film: Music by Prudence, a 33-minute documentary about a disabled Zimbabwean singer. "Forever in front of my name is the words, 'Oscar-winning filmmaker Roger Ross Williams,'" he says now.

"That will be my title for the rest of my life, and what an honor that is!" Williams shares with A.frame. "It's a responsibility and an honor at the same time. And I think about my Oscar often actually — because I'm always reminded of it — and I think about what that means to other people who look like me, whether for the LGBTQ+ community, or the Black community, or the Black, gay community. What it means to them that they, too, can aspire to Oscar greatness."

Over the ensuing decade, the New York-based filmmaker has been nothing if not prolific. He directed 2013's God Loves Uganda, 2016's Oscar-nominated Life, Animated, for which he received his second Oscar nomination, and 2019's The Apollo. This year alone, he's helmed the documentaries Love to Love You, Donna Summer (with co-director Brooklyn Sudano) and Stamped From the Beginning, as well as the docuseries The 1619 Project and The Super Models (with co-director Larissa Bills).

But Williams hadn't considered venturing outside of the doc world until Life, Animated. "I actually never thought about it," he recounts, "and then when I was nominated for an Oscar again — which, you're lucky once! — when that happened, Amy Ziering, who is an Academy member, said to me, 'You should direct narrative scripted films, because Life, Animated feels like a narrative scripted film.' I remember her saying that and a light went off. And I didn't again think about it until I met Cassandro."

Cassandro is the stage name of Saúl Armendáriz, also known as the Liberace of Lucha Libre. In 2016, Williams was tapped to direct a short documentary about Armendáriz for The New Yorker. The 13-minute film, The Man Without a Mask, looks back on Armendáriz's improbable rise to stardom as a flamboyant exótico in the hyper-masculine world of wrestling in Mexico. In Cassandro's story, Williams saw the makings of an underdog drama, one that would star Gael García Bernal in the title role.

"When I met Cassandro, I don't know what hit me — it was like a lightning bolt hit me," the filmmaker says. "The first day, there was a point during the interview where I was in tears, just inspired by his story, and he was in tears, and I turned to him and I said, 'Oh my god, you're my first scripted film.'"

A.frame: Why a scripted film? Why not a feature documentary? What was it that made you want to tell Cassandro's story in a different medium?

I think it's because I love to challenge myself as a storyteller. I made a VR piece [2019's Traveling While Black] and that was challenging, and I wanted to challenge myself again. But also, there was something about the spectacle of that world. With a documentary, you're restricted to what is there, but with all the tools of cinema, I could create. And I didn't really know that power until I actually started making the movie. I realized that when production design and costume design and all the branches of the Academy come together, it creates magic. And I completely fell in love with the process.

Everything in the frame tells the story, and you can manipulate everything in that frame. I didn't think about that as a documentarian, because I go into a room, and I'm like, "OK, where should I put the camera?" [On Cassandro,] I got to decide everything. Like, Mariestela Fernández, the brilliant costume designer and a legend in Mexico, she created all those luchador outfits. In Mexico City, she has a huge studio with a team of seamstresses sewing these costumes, and she's showing me the different masks and going, "And this is what I think for Sabrina, and this is the persona for this person," and having the time of her life. And I was like, "Oh my god, this is so fun!" So, that got me seduced.

Then there's [production designer] JC Molina, who is a gay Mexican-American man from the border who worked on [Beyoncé's] Lemonade and designed The Weeknd's Super Bowl halftime show. He's a genius, and he's drawing and creating these incredible worlds for Cassandro. That just blew me. He's building these sets, and I was like, "This is incredible." And then Matias Penachino, the DP, I had created a whole mood board and a color palette for the film. Matias also created a mood board and a color palette, and they were exactly the same! We were all on the same page.


You touched on the differences, but after so many years working in documentary, what skills were you able to seamlessly carry over?

Well, the big issue for me was actors and how to work with actors, because obviously I'd never worked with actors. I was terrified of actors. And I still am a little afraid of actors, because they're the unknown and I don't know how you operate them! So, I was invited to the Sundance Directing Lab and the Sundance Screenwriting Lab, and there, one of the greatest actors in the world took me under his wing and said, "I'm going to help you get over your fear of working with actors." And that actor's name is Robert Redford.

If anyone can help you get over your fear of actors, it's going to be Robert Redford.

He started the Sundance Institute because he wanted to work with directors and help them make their movies. The lab is legendary because all the greatest directors — Paul Thomas Anderson, the Coen Brothers, Quentin Tarantino, Ryan Coogler, Dee Rees — all started at the lab with their first projects. You're always aware of that. But Redford told me, he said, "What is it that you do as a documentarian?" And I said, "I try to get people to relax and open up, and be honest and truthful, and tell me their truth and tell me their story." And he goes, "Well, that's exactly the same thing you do with actors, except you're better at it, because you're doing it with real people, who are harder. Actors are professionals, so you can tap into that. You talk to an actor the same way you would talk to the subject of a documentary." Once he said that, a light went off and I was like, "Oh, you mean I can actually get actors comfortable and talk about their own experiences and their own lives?" And he's like, "Yes."

And then I remember another one of the advisors, Kasi Lemmons, she took me aside and goes, "You can calibrate actors. You can even talk to actors while you're rolling." I was like, "What?! You can talk to an actor while the camera is rolling?" It becomes a sacred thing. I can say, "Your father's talking to you right now, and he's telling you how disappointed he is," while the camera's rolling and the sadness comes over their face. I love it. I love learning new things, and it's this incredible learning experience. I had dinner with — not to name-drop, but — Ron Howard, and I said to him, "I've watched your masterclass, like, 10 times. You taught me how to direct."

Roger Ross Williams and Saúl Armendáriz attend a screening of 'Cassandro.'

Do you remember the first time you saw Gael fully transformed into Cassandro, with the hair and the makeup and the outfit?

Yes, absolutely. I'll never forget that moment. It was a screen test. We built a little set in the basement of the production offices in Mexico City, and Gael came down in full makeup and hair and I started crying. I cry a lot, but I just couldn't believe the transformation and I couldn't believe how much he was owning the character! We did this screen test and I was overwhelmed. It wasn't even the full crew — which is really overwhelming — but it was a pared-down crew, but still. It was a set, and he was full Cassandro, and I just couldn't believe it. I was just emotional and just blown away.

What was it like showing the movie to Saúl for the first time?

It was also an emotional experience where I just cried a lot. Two weeks before we started principal photography, the real Saúl had a stroke, and he was in a wheelchair the whole time we were shooting and unable to speak. And then we went into post and edit and everything, and that went on forever. And then finally, it was time to show him the film. So, David Teague, the co-writer, and I flew down to El Paso and Amazon rented the big amazing art deco theater for an audience of one. It was just Cassandro and his friend, Pepe, who's also an exótico, and they sat in the middle of the theater with this giant screen in front of them. We sat behind them, and when his mother came onscreen, he yelled, "Mama! Mama!" And then the triumphant scene in the fight with El Hijo del Santo, he stood up and he raised his hands in the air, mimicking the action on the screen. And he was crying. Tears were streaming down his face. I could cry now thinking about it. It was the best screening in my life.

By John Boone


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