The only woman to win an Oscar for playing a man
Gender politics has always been a hot-button topic that Hollywood has embraced. Often it was shameful coverage, including now-difficult-to-watch films portraying “othered” individuals in either tragic or evil roles. There’s been a major reckoning within the cinematic world since then, but it’s only been relatively recent.
Movies in recent years have opened the doors to trans men and women, not least including Karla Sofia Gascón, who, as an openly trans woman, was the first to be in with a chance of winning ‘Best Actress’ at the 2025 Oscars. She may well have won the award for her role in Emilia Perez had it not been for the unearthed controversial social media posts which seemed to end her campaign.
Still, progressive movies have been kicking around for decades. Some Like It Hot managed to mine comedy that still resonates today as two straight men pretend to be women in order to hide from the mafia. Jaye Davidson managed to score an Oscar nomination for his role in The Crying Game, even as his depiction eventually led to his early retirement from acting due to the limited roles and harsh backlash he received.
But Hollywood often seems to take two steps back with every step forward. Such is the case with the 1982 film The Year of Living Dangerously. In the film, Mel Gibson’s Australian television correspondent makes his way to Jakarta, Indonesia. There, he meets Billy Kwan, a Chinese-Australian local photographer who helps him manoeuvre through the politically turbulent climate.
For the role of Kwan, director Peter Weir didn’t look into the large number of real-life Chinese-Australians who inhabited the island continent at the time. Originally, Weir chose choreographer David Atkins, a white Australian man, for the role. When Atkins and Gibson didn’t have the chemistry that Weir was looking for, he decided to recast the role. That’s when he decided to make an outside-the-box choice: Weir cast American actress Linda Hunt in the role.
A well-known theatre actor before moving over to film, Hunt had only made her film debut two years earlier in the Robin Williams-helmed adaptation of Popeye. Still, a photo of Hunt was all that Weir needed to be convinced to cast her. With the help of extensive makeup, Hunt went from being a white American woman to a Chinese-Australian man.
While there had been a long history of gender swapping in entertainment, Hunt was the rare case of a modern-day performance where the actor in question wasn’t hiding their true gender. Hunt wasn’t acting as a woman pretending to be a man: her character was a man who happened to be played by a woman. That distinction would become legendary when Hunt was nominated for an Oscar.
At the 56th Academy Awards, Hunt went up against powerhouses like Cher and Glenn Close in the ‘Best Supporting Actress’ category. When she won the award, Hunt became the only actor to ever win an Oscar for portraying a character of the opposite sex. Naturally, her performance in the 21st century doesn’t feel quite as comfortable.
While Hunt’s role would likely go to an actual Chinese actor today, Hunt’s performance in The Year of Living Dangerously remains moving nonetheless.
