Gender is a fluid concept, and cross-dressing in acting is a centuries-old tradition. Over the years, many actors have donned facial hair, dresses, prosthetics, and wigs — and many have given a masterful performance. From Shakespearean tragedies to ’90s comedies, all sorts of genres feature cross-dressing storylines. Of course, there are also biopics, dramas, and procedurals in which actors have played transgender characters. Let’s take a look at the actors who have masterfully played another gender.
Angelina Jolie in Salt
Interestingly, 2010 action thriller Salt was originally written and produced with a male protagonist in mind. More specifically, action star Tom Cruise was attached to play Edwin Salt, an agent who had to rescue his family. When Angelina Jolie signed up, the storyline changed and the lead character became Evelyn Salt.
In the movie, Jolie’s character had to dress as a man, and the actress spent hours in makeup as a result. With a latex face and various fake features, Jolie’s husband and kids didn’t recognize her.
John Travolta in Hairspray
The original Hairspray movie was released in 1988, and featured legendary drag queen Divine as Tracy Turnblad’s larger than life mom, Edna. When the musical rom-com was remade in 2007, Grease actor John Travolta stepped into Edna’s shoes, donning a 30lb fat suit, a beehive wig, and high heels.
During filming, Travolta was in makeup for approximately five hours per day, though he admitted that he enjoyed the role. This part is quite a departure from Travolta’s other, more serious roles.
Patrick Swayze in To Wong Foo
Road comedy movie To Wong Foo, Thanks for Everything! Julie Newmar features actors Wesley Snipes and Patrick Swayze as drag queens Noxeema Jackson and Vida Boheme. At the time, the role of Vida was hot around town — with actors like Mel Gibson, Robin Williams, and Robert Downey Jr. all auditioning in drag.
Patrick Swayze was one of the last to audition, but he was desperate for the part. He used his own makeup team, and walked around the city passing as a woman.
Cate Blanchett in I’m Not There
Musical drama I’m Not There features six different actors depicting different facets of musician Bob Dylan’s life. Among those actors are Heath Ledger (in his final film), Richard Gere, and Cate Blanchett. Playing someone of another gender, Blanchett is Jude Quinn, the electric guitar-wielding version of Dylan.
Critics praised Blanchett’s performance, and Anthony DeCurtis commented that “it’s hard to imagine that any male actor, or any less-gifted female actor for that matter, could have lent such rich texture to the role.”
Barbra Streisand in Yentl
Based on the 1975 play, musical rom-com Yentl features the inimitable Barbra Streisand as a Jewish girl in Poland. In the film, Streisand’s character masquerades as her brother in order to receive the same education as her male peers.
Barbra Streisand was aware of the discrimination that Yentl portrays, and didn’t put her name on the script — which she co-wrote — in case it affected people’s perception of it. Thankfully, the actress and singer won a Golden Globe for directing the much-loved musical.
Glenn Close in Albert Nobbs
Actress Glenn Close went through an incredible transformation in order to play someone playing someone of another gender. In the 2011 British-Irish drama Albert Nobbs, the actress portrayed a 19th-century woman who disguised herself as a man in order to work as a butler.
As we’ve seen so far, there are many movies, plays, and books where female characters disguise themselves as men in order to survive or flourish. Even Disney has gotten in on this trope with action-adventure movie Mulan.
Amanda Bynes in She’s the Man
Noughties kids went wild for Shakespearean rom-com She’s the Man upon its release in 2006. The sports movie is inspired by Twelfth Night, and boasts an enthusiastic Amanda Bynes in the lead role.
The Nickelodeon star played Violet Hastings, a teenager who impersonates her twin brother in order to get on his school’s soccer team. Bynes later admitted that she didn’t enjoy watching herself play another gender in the movie, and had “a strange and out of body experience.”
Eddie Redmayne in The Danish Girl
Loosely inspired by the lives of Danish artists Lili Elbe and Gerda Wegener, The Danish Girl is set in mid-1920s Copenhagen and follows Elbe (Eddie Redmayne), one of the first known recipients of reassignment surgery.
Now, it’s no secret that the biographical romantic drama caused quite a stir upon its release in 2015. But, despite the fact that it was criticized for portraying historical events inaccurately, Redmayne was unsurprisingly nominated for an Academy Award.
Eddie Murphy in The Nutty Professor
From one Eddie to another, let’s turn to Eddie Murphy’s numerous performances as someone of another gender. The actor plays female characters Mama Anna Klump and Granny Klump in The Nutty Professor as well as its sequels, and Rasputia Latimore-Rice in Norbit.
Despite what you think about Murphy’s movies, you can’t deny that the man makes a good woman. Apparently, the actor refused to shave his mustache, but was otherwise in good spirits during his three and a half hours of makeup each morning.
Michael J. Fox in Back to the Future Part II
Hilariously, in the first sequel to sci-fi blockbuster Back to the Future, actor Michael J. Fox plays a future version of his own daughter. We know these movies get a little weird when it comes to interfamilial relationships, but we guess it makes sense that Marty McFly’s future offspring would look just like him.
Critics weren’t so sure, with Variety commenting that using the same actors in “some very cheesy makeup” strains credibility. We’re not sure credibility is what they’re going for.
Hugo Weaving in Cloud Atlas
Sci-fi epic Cloud Atlas is one of the most expensive independent movies ever made. Made by The Matrix directors — the Wachowskis sisters — the movie features several roles that defy gender norms. In one of those is British actor Hugo Weaving, as the vicious Nurse Noakes.
Cloud Atlas split audiences and critics, but was praised for being ambitious and multi-layered. The movie ended up on a range of Best Film and Worst Film lists, but Weaving’s performance is undeniably masterful.
Hilary Swank in Boys Don’t Cry
For her role as trans man Brandon Teena in 1999 biopic Boys Don’t Cry, American actress Hilary Swank took home an Oscar. Swank was chosen for the role based on how similar her personality was to the character’s real life counterpart, and lived as a man for one month in preparation.
Boys Don’t Cry is a tough watch as it deals with sensitive issues. Reflecting on the role, Swank says she wouldn’t take it today as it would be better suited to a trans actor.
Quentin Crisp in Orlando
1992 period drama Orlando features several gender bending performances, beginning with this one. The movie is loosely based on Virginia Woolf’s novel and opens in the Elizabethan era. With an elaborate wig and many layers of costumes, English actor Quentin Crisp depicted Queen Elizabeth when he was 83 years old.
Director Sally Potter commented that Crisp was the “Queen of Queens…particularly in the context of Virginia Woolf’s gender-bending politics.” Unfortunately for him, the ornate costume left blisters on the actor’s body.
Tony Curtis and Jack Lemmon in Some Like it Hot
For many people, Tony Curtis and Jack Lemmon’s turn as women in Some Like it Hot is an iconic gender bending performance. The black and white rom-com also starred blonde bombshell Marilyn Monroe, and was directed by the famed Billy Wilder.
Based on a 1935 French film, the movie follows two musicians who dress in drag in order to escape a group of gangsters. At the time, the cross-dressing plot made this movie controversial. Now, it’s considered one of the best ever made.
Willem Dafoe in The Boondock Saints
Vigilante movie The Boondock Saints is a cult hit, and features tough guy Willem Dafoe as someone of another gender. In the movie, Dafoe plays FBI agent Paul Smecker, who decides to transform into a woman in order to infiltrate the Russian mob’s headquarters.
As we’ve seen, many movies with gender-bending plots include men dressing as woman in order to seem unthreatening. In fact, this can also be seen in Disney’s Mulan when the Chinese soldiers dress as concubines.
Tilda Swinton in Orlando
We’ve already tipped our hat to Quentin Crisp’s masterful gender bending performance in Orlando, but the main prize must go to the film’s protagonist, Tilda Swinton. The English actress is known for her arthouse roles, and fully commits to the role of the androgynous young nobleman.
To add more layers of gender, Orlando’s plot later sees Swinton’s character transform into a woman. Clearly, like in this movie’s modernist source material, gender in this story is unquestioningly fluid.
Robin Williams in Mrs. Doubtfire
Who doesn’t have fond memories of watching Robin Williams’ masterful performance as Scottish nanny Mrs. Doubtfire? In the role, the high energy actor delighted audiences around the world with prosthetics, pantyhose, and that inimitable accent.
In fact, Robin Williams wanted to play main character Daniel Hillard so much that he signed up before reading the script. Thank goodness he did, or we would never have experienced the joy of watching a man in drag joyfully dance to “Dude (Looks Like a Lady).”
Julie Andrews in Victor/Victoria
Gay favorite Victor/Victoria tells the story of a young singer in 1930s Paris who pretends to be a male drag queen. The musical comedy is Academy Award winning, and features the legendary Julie Andrews as both Victoria Grant and Count Victor Grazinski.
As in many movies with fluid gender roles, Victor/Victoria depicts gender as performative and layered. The movie is based on a German film, and has been turned into a Broadway musical. It’s beloved by both critics and audiences — give it a go!
Martin Lawrence in Big Momma’s House
Comedy Big Momma’s House wasn’t received well by critics, but it was a huge box office hit. The movie stars Martin Lawrence as an FBI agent who must disguise himself as an elderly woman in order to solve a crime.
Interestingly, the prosthetics in this movie were done by the same special makeup effects artist that created Robin William’s look in Mrs. Doubtfire. Big Momma’s House has been called a gimmick, but some critics praised Lawrence’s performance as a woman.
Tom Hanks in Bosom Buddies
When we think of acclaimed actor Tom Hanks, we generally don’t think of the 1980s sitcom, Bosom Buddies. Incredibly, this comedy was Hanks’ big break, and the show’s creators didn’t even intend for it to feature cross-dressing.
After mentioning cross-dressing hit Some Like It Hot in a pitch meeting, the creators had to change their initial premise. The show followed two men who disguised themselves as women in order to live in a women-only hotel. We’re not sure that premise would fly these days.
Jude Law in Rage
The creators of satirical mystery movie Rage claimed that they were creating a new genre with the film. It premiered on mobile phones and online at the same time as in cinemas and on DVD, and it featured English actor Jude Law as drag queen Minx.
With his long black hair and made-up face, Law looks almost unrecognizable playing someone from another gender. Despite a star-studded cast — including Steve Buscemi and Judie Dench — Rage was a massive flop.
Meryl Streep in Angels in America
Based on the Pulitzer-prize winning play of the same name, Angels in America is a sprawling mini-series based on the AIDs crisis in the US. The HBO series was a major hit, and took home awards in every eligible category at the Emmys, including all four acting categories.
Masterful actor Meryl Streep plays multiple characters in the series, including nonagenarian “The Rabbi.” With a full beard and a Streep-worthy accent, you would barely know this male character was played by a woman.
Rupert Everett in St Trinian’s
There are quite a few St Trinian’s movies, starting with The Belles of St. Trinian’s, made in 1954. Following from Scottish actor Alastair Sim in the original film, the 2007 reboot also casts a male actor in the role of the chaotic school’s eccentric headmistress, Camilla Dagey Fritton.
In the movie, English actor Rupert Everett plays both Camilla and her brother Carnaby. The actor reprised his role for St Trinian’s 2: The Legend of Fritton’s Gold, and there are talks of a new installment.
The Wayans Brothers in White Chicks
Is it accurate to say that the Wayans brothers’ turn in White Chicks is a masterful performance? Whilst some might say the movie is a crass and poorly rated noughties mistake, others will argue that it’s a cult classic featuring Terry Crews singing “A Thousand Miles.”
For those who haven’t seen it, White Chicks follows the story of two FBI agents who go undercover as women to solve a crime. Now, considering that the film has basically become a cult classic, we’d say it’s worth a watch!
Jeffrey Tambor in Transparent
Transparent (2014-2019) revolves around an L.A. family and their lives following the discovery that their parent is a trans woman named Maura — played by Jeffrey Tambor.
The award-winning show is rated very highly and contains an impressive cast, as well as extremely profound moments. Despite this, though, Tambor left the series in 2018 due to a series of allegations made against him.
Linda Hunt in The Year of Living Dangerously
When it comes to masterful performances of playing someone from another gender, Linda Hunt’s name comes up time and time again. In romantic drama The Year of Living Dangerously, the American actress plays a Chinese-American photographer with dwarfism. For the role, Hunt took home the 1983 Academy Award for Best Supporting Actress.
For the part, Hunt cut and dyed her hair, shaved her eyebrows, and padded her waist. She was the first woman to receive an Oscar for playing a character of another gender.
Whoopi Goldberg in The Associate
There are various films that follow a person from a minority group masquerading as a more powerful person in order to be perceived differently. In The Associate, Whoopi Goldberg’s character creates a fictional white male associate to do business on her behalf.
Of course, her plans go awry when people want to meet this man. Enter a makeover and complete transformation.
David Duchovny in Twin Peaks
Mystery horror series Twin Peaks is a cult hit, and often listed among the best TV shows of all time. Interestingly, one of its recurring characters is a transwoman DEA agent, played by The X Files alum, David Duchovny.
Aired in 1990, Twin Peaks’ depiction of a trans character was impressive, considering how other media often depicted trans people at the time. When Duchovny’s character reappeared in Twin Peaks: The Return, fans were happy to see that his character was now the FBI’s chief of staff.
Dustin Hoffman in Tootsie
In 1982’s Tootsie, we have another male actor playing a male actor, playing a woman. In this sense, Dustin Hoffman is playing a man playing a woman, rather than strictly playing a woman directly. In the film. Hoffman plays a volatile actor who must disguise himself as a woman in order to get work.
Tootsie was a huge success, and is considered a culturally and historically significant movie. Amusingly, Dustin Hoffman found himself shocked that he made a credible woman, but not a beautiful one.
Elle Fanning in 3 Generations
In 2015 comedy-drama 3 Generations, American actress Elle Fanning plays trans character Ray as he reconciles his gender identity with his loved ones. Because this movie was made in 2015, there was considerable controversy about Fanning’s casting as a trans man.
Many argued that the role should have gone to a trans actor, though the director argued that Fanning’s casting was appropriate. The movie didn’t do so well with critics either, with reviews spurning the “thinly written story.”
Gwyneth Paltrow in Shakespeare in Love
Shakespeare in Love is a period drama rom-com that stars Gwyneth Paltrow, Colin Firth, and Ben Affleck, among others. Paltrow plays the wealthy Viola de Lesseps, who disguises herself as a man to audition for a part in one of Shakespeare’s plays. Inspired by her, Shakespeare writes Romeo & Juliet, before discovering Romeo’s true identity.
The cross-dressing plot in this movie speaks to its Elizabethan source material, though Paltrow doesn’t exactly make a convincing man. Apparently, she wore a beanbag in her tights for the role.
Tilda Swinton in Suspiria
The 2018 remake of supernatural horror movie Suspiria stars Dakota Johnson as a woman who enrolls at a German dance academy run by a coven of witches. Actress Tilda Swinton plays the school’s choreographer, but also had a secret role as elderly male psychoanalyst Dr. Klemperer.
Both Swinton and the movie’s director kept this role a secret, and even invented “real” psychoanalyst Lutz Ebersdorf, claiming he played the role. In reality, it was Ms. Swinton with a whole lot of prosthetic makeup.
Cillian Murphy in Breakfast on Pluto
We have to give credit where credit is due — Irish actor Cillian Murphy makes a very attractive woman. In comedy drama Breakfast on Pluto, we have yet another role where a cisgender actor plays a transgender character. In the film, Murphy plays a trans character searching for their biological mother in 1970s Ireland and London.
In preparation for the role, the Peaky Blinders actor studied women’s body language and took lessons from a drag queen. This movie is based on a book of the same name.
Tyler Perry in Diary of a Mad Black Woman
Diary of a Mad Black Woman is Tyler Perry’s feature film debut. In the comedy-drama and its sequels, Perry stars as Mabel “Madea” Simmons, a matriarch based on Perry’s own mother and aunt.
While some people have criticized Perry’s use of stereotypes when it comes to portraying someone of another gender, the filmmaker has argued that his characterization is affectionate. Interestingly, Perry’s movies tend to have poor reactions from critics but extremely high box office numbers.
Jared Leto in Dallas Buyers Club
There was some controversy around Jared Leto’s casting as trans woman Rayon in 2013’s Dallas Buyers Club. The movie, based on a true story, follows a patient trying to seek treatment, and includes various composite characters based on a range of real patients, activists, and doctors.
Leto took home the Academy Award for Best Supporting Actor for this role, and main character Matthew McConaughey took home the Best Actor award.
Ben Whishaw in Cloud Atlas
We’ve already had one gender bending performance from 2012’s Cloud Atlas on this list, with Hugo Weaving’s turn as the evil Nurse Noakes. This movie follows several individuals in different settings and time periods, with each actor playing a range of characters.
Paddington star Ben Whishaw plays female character Georgette in the London part of the movie. This film deals broadly with the idea of souls over time, so it makes sense that different actors inhabit different people. Plus, Ben looks lovely as a woman.
Adam Sandler in Jack and Jill
Here we have another gender-bending performance that might be more cringe than masterful. In a dual role, Jack and Jill sees Adam Sandler play twins, and as the movie’s poster says, “It ain’t pretty.”
This movie tries to rely on Sandler in drag as its main joke, but it really wasn’t well-received. Jack and Jill is actually considered one of the worst movies ever made — and took home Razzies for Worst Picture, Worst Actor, and Worst Actress. Ha!
RuPaul in The Brady Bunch Movie
Perhaps unsurprisingly, drag star RuPaul makes a pretty convincing woman in The Brady Bunch Movie and its sequels. In the movie, the host of RuPaul’s Drag Race plays a female guidance counselor — and looks spot on in his wig, headband, and makeup.
This ’90s movie transported the original sitcom characters from their ’70s setting into the modern-day. Critics remarked that the “part homage, part spoof” movie was a clever adaptation, and full of nostalgia for original fans of the show.
Bradley Whitford in Transparent
We’ve already mentioned Amazon’s award-winning series Transparent, a show that follows a family and their responses when the patriarch of the house comes out as a trans woman.
Cisgender actor Bradley Whitford took home an Emmy award for his portrayal of Marcy in the show, and went on to depict German physician Magnus Hirschfeld in a later season. Transparent is very highly rated, and an important show about gender identity.
John Lithgow in The World According to Garp
Audiences might recognize actor John Lithgow as Winston Churchill from The Crown, or the creepy Roger Ailes from Bombshell. Before that, the American actor starred in The World According to Garp, a comedy-drama starring Robin Williams in the lead role.
In the 1982 film, Williams’ mother runs a shelter for women, and Lithgow plays a transgender resident named Roberta Muldoon. This role is considered one of the first sympathetic trans characters in a mainstream movie.