Today: October 6, 2026

Cinema’s Greatest Gender Benders

From Shakespeare to Monty Python, cross-dressing has long been a British comedy staple. Put a bloke in a frock and watch the audiences roll in the aisles. However outside of the comedy arena, the challenge of portraying a different gender convincingly on screen is one of the toughest that most actors will ever face. So join us as we raise a glass to some of cinemas most outstanding gender benders …

The Year Of Living Dangerously (1982)
Adapted from the novel by Christopher Koch this glossy big screen adaptation featured two of Hollywood’s biggest hitters in the roles of star crossed lovers Guy and Jill: Sigourney Weaver and Mel Gibson. However it was unknown actress Linda Hunt who stole the film and a Best Supporting Actress Oscar for her role as diminutive male photographer Billy Kwan. She played the role without makeup, simply cutting her hair and wearing padding to give herself a more ‘male’ body shape.

Breakfast On Pluto (2005)
Neil Jordan’s dark comedy stars Cillian Murphy as Kitten, a transgender woman searching for her long lost mother in 1970s Ireland. Jordan had previously explored gender bending in his 1992 feature, The Crying Game but Murphy’s flirtatious and poignant character is the credible creation on which this unflinchingly surreal drama hinges.

Orlando (1992)
Some gender bending actors may revel in playing ultra macho or super feminine creations, but what makes Tilda Swinton’s Orlando so believable is the profound subtlety she brings to the role. Orlando – who changes sex during the course of the film – is blessed with immortality but cursed by being unable to fulfill society’s expectations of how a man or woman should behave. Swinton is utterly believable both as the feminine, male Orlando and boyish female Orlando. Quentin Crisp makes a killer Queen Bess too.

Animal Factory (2000)
Prison drama Animal Factory was a fairly pedestrian affair. But it was saved from being utterly forgettable by a blistering come-back performance by Mickey Rourke as Jan the Actress. Rourke is, let’s be honest, no Cillian Murphy. He’s no androgynous beauty. But Jan is no clichéd drag queen stereotype either. With the oiled body of a boxer, broken teeth and frilly panties, Jan the Actress is a fully-realised, complex character. If you need a reason to see this film, then Jan’s monologue about going to “Paris, France” is it.

Homicidal (1961)
Director William Castle is better remembered today as the king of kitsch movies and Homicidal is remembered today as a bargain basement Psycho (which was released in the same year). While Norman Bates carries out his murders disguised as Mother, the murderer here is masquerades as both a man and a woman. Joan Marshall used the pseudonym Jean Arless to further confuse audiences who genuinely didn’t know if ‘Jean’ was a male or female.

 

 

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