Best Performances Where A Woman Played A Man (& The Best Where A Man Played A Woman)

Since the silent film era, there have been films where men and women have dressed as their opposite gender. Until the 1970s, this was always played for laughs and comical misadventures, most famously in Billy Wilder’s 1959 comedy classic, Some Like it Hot, which found Jack Lemmon and Tony Curtis posing as women to hide from mobsters.

In the past 30 years, the filmmaking world has explored gender roles more deeply (in films about the transgender community and crossdressing) through unique casting choices and films that speak to the role of gender in society. Ryan Murphy, for example, made history on television with his honest portrayals of gender in shows such as Pose and An American Horror Story. Here are the five best roles where women played men and five more where men played women.

10 Cillian Murphy – Breakfast On Pluto

Already a risk-taking actor, Cillian Murphy took on the role of Patrick “Kitten” Braden, a young transgender female in 1970s London. The film took on how a person can be shunned for their gender identity.

Murphy was praised for his performance in Neil Jordan’s critical hit and was nominated for Best Actor awards in many international film ceremonies, including the Golden Globes.

9 Glenn Close & Janet McTeer – Albert Nobbs

Glenn Close and Janet McTeer played Albert Nobbs and Hubert Page, respectively. Nobbs was a woman who abandoned societal expectations to work as a butler in 19th century Ireland. Page was the transgender man who helped Nobbs find his true self.

Both Close and McTeer were Oscar-nominated for their powerful work as two people living in a dangerous time for transgendered men and women.

8 Divine – Hairspray

Divine was perhaps the most famous drag queen of her day. The underground films of director John Waters made her a cult star but it was Waters’ 1988 comedy-musical Hairspray that endeared her to mainstream audiences and critics.

Harris Glenn Milstead, whose stage name was Divine, played the nagging mother to a teen daughter who wanted to dance on a local TV dance show. Divine played the role with sass and wit and made believable her relationship with her husband (Jerry Stiller) and her daughter (Rikki Lake).

7 Tilda Swinton – Orlando

A unique and ethereal tale, Tilda Swinton came to the notice of critics worldwide with her role in Sally Potter’s 1992 oddity, Orlando. Swinton plays a young nobleman who struggles with his identity in the world after Queen Elizabeth I orders him to never grow old.

Swinton took a big risk playing a nobleman and it paid off with much critical praise and award nominations. This would be the film and role that would give Swinton her long and successful (and Academy Award-winning) career.

6 Jaye Davidson – The Crying Game

Neil Jordan’s 1992 classic The Crying Game was a multiple Oscar nominee (and winner for Best Original Screenplay) and took the American and international box office by storm. Jaye Davidson played a transgender woman who won the heart of an IRA soldier.

Davidson’s “reveal” by the end of the film was the secret that sold tickets, but it was his honest and soulfully beautiful performance that won over the hearts of audiences and critics everywhere. This was a love story that broke down gender barriers and allowed it to be about the heart, rather than societal prejudices.

5 Cate Blanchett – I’m Not There

Todd Hayne’s masterful film, I’m Not There examined the long career of Bob Dylan through different times of his life. Through his music, Haynes created the Dylan character that he believed would’ve created those works during that particular time.

Actors Christian Bale, Richard Gere, and Heath Ledger would play various manifestations of the songwriter/poet, but it would be Cate Blanchett who made the biggest splash. The actress played “Jude Quinn,” a version of Dylan during his late 60’s Don’t Look Back phase. Blanchett was Oscar-nominated for her rather astonishing portrayal, where she completely morphed into late-60s Bob Dylan.

4 Meryl Streep – Angels In America 

Mike Nichols adapted Tony Kushner’s mammoth play Angels in America for HBO and the miniseries is considered to be one of the great films to deal with the AIDS crisis. It was also one of the most critically-lauded and award-winning films in HBO’s history.

Meryl Streep played a few different roles, but her most astonishing was “The Rabbi.” Buried under award-winning makeup, a full beard, and a flawless male Jewish accent, Streep’s work here is one of the most jaw-dropping of her career. The actress is completely lost as she brings the 90-plus-year-old Rabbi to full life.

3 Dustin Hoffman – Tootsie

Sydney Pollack had the biggest hit of his directorial career with 1982’s gender-switch comedy Tootsie. The film received multiple Oscar nominations and was one of 1982’s top 10 box office successes.

Dustin Hoffman turned what could’ve been a cliched gimmick into a realistic performance that challenged gender norms in Hollywood and television. Hoffman considers this his finest work.

2 Hilary Swank – Boys Don’t Cry

Kimberly Pierce’s 1999 film Boy’s Don’t Cry told the powerful real-life story of Brandon Teena, a transgender man who was murdered due to his identity.

Hilary Swank won an Oscar for her work as Teena. The actress showed the heart and humanity in Brandon Teena and made him more than a tragic headline.

1 Linda Hunt – The Year Of Living Dangerously

The early 1980s were a boom for Australian films in America and Peter Weir proved himself to be one of the leaders. Already respected in his home country for films such as Picnic at Hanging Rock, The Last Wave, and Gallipoli, Weir made his mark in this country with his 1982 film The Year of Living Dangerously, a story about a reporter (Mel Gibson) and his friend and photographer (Linda Hunt) in early 60s politically-troubled Indonesia.

Linda Hunt played “Billy Kwan,” a diminutive male photographer who has his soul and heart completely shattered by experiencing how the Indonesian government destroyed the lives of children and their families under the dictatorial rule. Hunt, in only her second feature film, was the conscience of the piece and was rightfully praised by critics, going on to win the 1983 Oscar for Best Supporting Actress and starting a long and successful career as a character actress.