The first person to win an Oscar while playing the role of a person of the opposite sex occurred in 1983. The Oscar for Best Supporting Actress went to a woman who played the role of a male photographer. What was the name of the film and the name of the w

In a truly unique moment in Academy Awards history, Linda Hunt took home the 1983 Oscar for Best Supporting Actress for her role in the political thriller, The Year of Living Dangerously. Her win was groundbreaking because she convincingly portrayed Billy Kwan, a male Chinese-Australian photographer who serves as the film's moral center. The performance was not for comedic effect or a temporary disguise, but a complete and serious transformation into a character of the opposite sex.

The casting choice was a result of director Peter Weir's difficulty in finding a male actor who fit the specific physical and intellectual requirements for the part. After an extensive and unsuccessful search, Weir expanded the casting call to include women. Linda Hunt, with her small stature and powerful presence, delivered an audition that won her the role. To prepare, she cut her hair short, dyed it black, and fully immersed herself in the character's male mannerisms, creating a performance so seamless that many viewers were initially unaware an actress was playing the part.

Hunt's victory remains a singular achievement. While other actors have since won Oscars for cross-gender portrayals, those roles have typically involved depicting transgender characters, such as Hilary Swank's win for Boys Don't Cry. To this day, Linda Hunt is the only person to have won an Academy Award for playing a fictional, cisgender character of the opposite sex, a powerful testament to her transformative acting ability.