What Made ‘Boys Don’t Cry’ One Of The ‘Biggest Challenges’ In Casting

The answer to the question of “Who can play what role?” — in terms of race, gender identity, sexuality, physical ability or age — has changed over the years.

And when it comes to films about transgender people — like Boys Don’t Cry in 1999, Transamerica in 2005 and Dallas Buyers Club in 2013 — there’s been a bit of a reappraisal in recent years, about whether the trans roles in those films should have gone to trans actors.

The argument makes sense. Even today, there are very few opportunities available for trans performers. In the five years leading up to 2021, the year of GLAAD’s latest report on the “quantity, quality and diversity” of LGBTQ characters in major studio films, they found only one transgender character.

But for the filmmakers behind the 1999 film Boys Don’t Cry, the question of what kind of actor could — or should — have embodied the central role is a complicated one.

How ‘Boys Don’t Cry’ was cast

The film is a fictionalized version of the real-life story of Brandon Teena, a 21-year-old transgender man who in 1993 was beaten, raped and later killed. Brandon’s story rose to national attention with coverage in publications like The New Yorker and Playboy. A documentary was released in 1998, and then the narrative film Boys Don’t Cry in 1999.

The actor selected for the starring role was Hilary Swank, a cisgender woman. She earned widespread praise for her portrayal and won the Academy Award for best actress in 2000.

But at the outset, co-writer and director Kimberly Peirce (he/she) had intended to cast a trans man. Over the course of more than three years, Peirce conducted hundreds of interviews — both as research for writing the film and in an effort to cast the central role.

Actress Hilary Swank holds her Oscar for Best Actress for her role in "Boys Don't Cry" at the 72nd Annual Academy Awards in Los Angeles on March 26, 2000.

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Hector Mata

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AFP via Getty Images

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And at the Academy Museum in Los Angeles, you can see Hilary Swank’s audition to play Brandon along with auditions from two trans men who were also considered: Silas Howard and Harry Dodge.

“We wanted to approach this very carefully,” associate curator Dara Jaffe told The Academy Museum Podcast. The museum got permission from all three actors to display their auditions side by side. “In any case where you're showing auditions of someone who didn't get the role, I think it's a bit sensitive. But especially given that Silas and Harry are both trans men and there has been a lot of discussion over the casting of Brandon Teena, and of course there's a lot of push now for roles such as that to be played and told by people who can authentically embody that experience, that real-life lived experience.”

Peirce says the auditions from Dodge and Howard “were part of my better understanding of that character.”

“I cry when I watch that stuff, because I see the beauty of Harry Dodge and the beauty of Silas Howard and the authenticity of the lives that they were living, and that I was living a very similar life, but mine wasn't captured on camera. And that we were all leaning in to try to capture the essence and the beauty of this story.”

The search for Brandon

“We went all over the country looking for someone to play this important role,” casting director Kerry Barden (he/him) told The Academy Museum Podcast host Jacqueline Stewart.

The outreach was mostly to non-professional actors and that while they ultimately went with “more traditional casting” in selecting Swank, Barden says there was a real effort to find someone who was trans, or from the LGBTQ community.

Barden’s credits include American Psycho, Dallas Buyers Club, Spotlight, The Help, and several films by director John Waters.

He says casting Boys Don’t Cry “at that point, and still partially is, one of the biggest challenges in casting I'd ever come upon.”

During the casting process for a film, Barden says, “usually it's not as in-depth as this was, and you don't have as much time. Usually we have a start date and with this, we didn't have a start date until we found Brandon. Because we couldn't make the movie without that.”

A trans journey

For Kimberly Peirce, the process of casting the film was also a very personal one. Peirce describes herself as a combination of trans and butch lesbian.

“It was such a fascinating journey because I was trying to figure out my own transness and my own butch lesbian-ness and, and all my desire,” she says.

Early on, while Peirce was starting to think about making Boys Don’t Cry while in grad school, “the first question that I was asked by my lesbian playwriting teacher was, ‘Is Brandon a lesbian, or is Brandon trans? Does Brandon want to sleep with women, or does Brandon want to be a man?’”

“Immediately people wanted to simplify it,” Peirce says. “They wanted to put Brandon into a category. And particularly because I was searching for my own identity, I knew that the last thing I wanted to do was simplify Brandon. So I went and interviewed trans people … It was like, 'Let me understand everything before I start simplifying.'”

And after hundreds of interviews, Peirce began to doubt they would ever find the right person for the role.

“Kerry [Barden] had done so much work and every night he would send me these tapes and I would just fall asleep watching them being like, ‘Oh my God, nobody's gonna get this human. This doesn't exist anywhere,” she said.

Hilary Swank first came to the filmmakers’ attention when Barden was out in Los Angeles, casting for another film. And at first, she didn’t seem like an obvious fit for the role to Barden.

“When Hilary came in,” Barden says, “it was like, ‘But you're so Julia Roberts. You're just such a girl, you know?’ And she just kept working it and working it. I mean, Kimberly put her through the mill.”

Peirce saw something different in Swank.

“Hilary's tape came in and she has a naturally angular face. She has those gorgeous brown eyes, and it's not that she passed necessarily as a man, it's that she blurred the gender line,” Peirce says. “So that was a real win that I had not found in almost every other actor that I looked at, other than the trans men and the drag kings.”

Peirce had Swank work with trans people, do voice training, and live as a man.

“So whatever we saw in the room was really the beginning of the journey,” Peirce says. “And we all had to, you know, check ourselves and say, 'We are about to entrust the most important role in this, that carries the entire movie, to this human being. Do they have what it takes and will they give it what it takes to succeed?'”

How might ‘Boys Don’t Cry’ be cast today?

Barden says he thinks today they would have a larger pool of trans talent to choose from, “and it would make it easier to do this film with a trans person in the lead.”

“And I think, you know, having given a voice to this trans community that was kind of nascent at that point,” Barden says, “I feel like that's part of what the legacy of this film is. You get to have these people that now are saying, ‘I can do this. I can be out there, I can be, you know, honoring my life journey and also be an artist that has a public profile without being slammed or being vilified.’”

Peirce agrees with Barden, that today there would be more trans and queer actors to consider for the role. A lot of that is due to progress and change within the queer community over the last 25 years.

“What you would probably have is people who identify as nonbinary, people who identify as trans, but maybe not having surgery and maybe not having hormones,” Peirce says. “So you would have a wider pool of people who were able to approach that role, and that would have been fascinating.”

Listen to the conversation

How do I find The Academy Museum Podcast?

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