Two Oscars, two transformations—and for the first, playing Brandon Teena in the utterly devastating Boys Don’t Cry, Swank cut her hair short, taped her breasts down and stuffed her pants (as Brandon, who was born Teena Brandon, does in the movie) and ventured out into her Los Angeles-area neighborhood, introducing herself as “Hilary’s brother, James.”
“I was treated so differently in public,” Swank told the New York Times in 1999. If shopkeepers thought she was a boy, they watched her more closely. And, she added, “If people couldn’t define what I was, they didn’t want to have anything to do with me.
Actually making the film, based on a tragic true story (Brandon was murdered on New Year’s Eve in 1993 by two men he’d counted as friends until they found out he was biologically female) was more upsetting than Swank had anticipated, so she had then-husband Chad Lowe join her on the set. “I told him I was having a really hard time getting through this,” she said. “I had to keep a little bit of distance from the fact that this actually happened to someone.”
Determined, compassionate commitment to do the character justice aside, Swank acknowledged to Variety in 2020 that if the film were made today, the role would be better served by a trans actor.
At the time it was made, Swank explained, “I mean, trans people weren’t really walking around in the world saying, ‘Hey, I’m trans.’ Twenty-one years later, not only are trans people having their lives and living, thankfully, [although] we still have a long way to go in their safety and their inclusivity, but we now have a bunch of trans actors who would obviously be a lot more right for the role and have the opportunity to actually audition for the role.”
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