Hilary Swank Regrets Her Oscar-Winning Role in ‘Boys Don’t Cry’

The past decade has marked a significant change in how transgender people are viewed in the media — and in the world more broadly. Academy Award-winning actor Hilary Swank brought large attention to the plight of trans victims of violence in the 1999 film Boys Don’t Cry.

Hilary Swank attends the Academy of Motion Picture Arts and Sciences' 10th annual Governors Awards at The Ray Dolby Ballroom at Hollywood & Highland Center on November 18, 2018 in Hollywood, California.
Academy Award-winning actor Hilary Swank | Steve Granitz/WireImage

Hilary Swank won an Oscar for playing murdered trans man Brandon Teena

Boys Don’t Cry is based on the real story of Brandon Teena, a trans man from Nebraska who was murdered in 1993. Teena’s death came five years before the murder of Matthew Shepard. Both of their deaths led to increased calls for hate crime laws for LGBTQ victims.

Director Kimberly Peirce first became interested in telling Teena’s story the year after his death. She auditioned over 100 female actors for the role and wasn’t satisfied with any of them; Swank was an unknown actor at the time and impressed Peirce with her audition tape.

Peirce said she did not want a “known actor” to portray Teena, making Swank a natural choice. Swank prepared for the role by dressing and living as a man for a month before filming, including binding her chest and reduced her body fat to accentuate her facial structure and refused to let the cast and crew see her out of costume.

Hilary Swank
Academy Award-winning actor Hilary Swank at the “What They Had” Press Conference at the Four Seasons Hotel on October 8, 2018 in Beverly Hills, California | Vera Anderson/WireImage

Hilary Swank won an Oscar for ‘Boys Don’t Cry’

Swank was lauded for her portrayal of Teena and earned her first Academy Award in 2000. At the time, many people didn’t see any issues with a cis woman playing a trans man. But times have changed.

The 2020 documentary Disclosure explores trans representation in media and touches on Swank’s groundbreaking role, and the legacy of cis actors playing trans characters such as Eddie Redmayne in The Danish Girl, Jared Leto in Dallas Buyers Club, and Jeffrey Tambor in Transparent.

It wasn’t until the mid- to late 2010s that trans actors began being cast in large numbers, thanks in large part to Ryan Murphy’s FX series Pose.

Hilary Swank
Oscar-winning actor Hilary Swank attends the Mon Cheri Barbara Tag at Postpalast on December 2, 2016 in Munich, Germany | Susi Bond/WireImage

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Hilary Swank regrets taking on the role in ‘Boys Don’t Cry’

In 2019, Swank spoke with Variety about the ramifications of her role in Boys Don’t Cry. She addressed the elephant in the room of her playing a trans man, and acknowledged that an actual transmasculine actor would have been a better fit to tell Teena’s story on screen.

“Twenty-one years later, not only are trans people having their lives and living, thankfully,” she said, “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.”

She added that “we still have a long way to go in their safety and their inclusivity.”