Actors and actresses playing a character that doesn't conform to their own gender identity is nothing new. In Shakespeare’s time, young boys routinely played the roles of female characters, as it was considered unseemly for women to act. However, these attitudes dissipated as time went on, and the word ‘actress’ came into existence in 1700. In modern times, both men and women are free to grace the stage, but there are still several instances of actors and actresses playing the role of a character of the opposite gender. For example, although a man may be chosen as well, a woman traditionally plays the role of Peter Pan. Whether this is done because the actor or actress was simply the best choice for the character, gender norms be damned, or for comedic effect, these 15 actors and actresses have nailed their roles as characters of the opposite gender.
15 Quentin Crisp – Orlando
When most people picture an aging Queen Elizabeth, they probably have a woman in mind, and not a man. However, in certain cases, this isn't always the case. Quentin Crisp was cast to play Queen Elizabeth in 1992’s Orlando. And not only did Crisp manage to win the part, he absolutely nailed the role. Clad in opulent queen’s garments, Crisp looked and acted the part with aplomb. Toying with gender roles in Orlando was seemingly perfect for the actor– read on to discover one more actress from this film on this list.
14 Tyler Perry – Madea
Whether Tyler Perry has ‘nailed’ his repeated roles as the elderly and "tough as nails" female character Madea, is debatable – Perry’s acting is the kind that you either really love or really hate. Whether you detest Perry’s films or can’t wait for the next one to come out, his paycheck seems to support the fact that everyone loves Madea. From May of 2010 to May of 2011, Perry reportedly made $130 million, so he must be doing something right. One thing we can all agree on, though, is Perry’s commitment to the character is undeniable – he always rocks his drag get ups.
13 Charlie Chaplin – A Busy Day
Charlie Chaplin is an icon, and is one of cinema’s greats, and although his role as a wife in the short 1914 film A Busy Day, is small, it undoubtedly deserves its place on this list due to Chaplin’s iconic and pioneering status. Chaplin adopts the female role through the use of props, such as clothing. There’s nothing like a heavy dress to make the switch from man to woman, right? The entire film, lasting a total of 6 minutes, is available on Youtube, if you’re interested in seeing one of film’s first gender benders.
12 Angelina Jolie – Salt
Angelina Jolie may be one of the most beautiful actresses in Hollywood, as well as one of the most beautiful women in the world, but she pulls off a masculine role in the 2010 spy film, Salt surprisingly well. Since the tough role was originally written for a man, Jolie’s cameo as a man is a nice nod to the original plans. Although, as most of us might imagine, this wasn't an easy task. Disguising herself as a man took pounds of prosthetics and several hours in the makeup chair, but Jolie came out looking pretty dapper.
11 Hugo Weaving – Cloud Atlas
The 2012 drama/sci-fi film, Cloud Atlas based on the popular book written by David Mitchell, plays with both gender and race with abandon. In fact, most of the actors and actresses in the film are cast to play several characters that lie outside of their own race and gender. One of the most notable instances of this is Hugo Weaving’s portrayal of the vicious Nurse Noakes. Although, it might actually help that Hugo didn't need to be an attractive woman – Nurse Noakes’ outsides are almost ugly as her interior.
10 Alec Guinness – Kind Hearts and Coronets
Like several of the actors and actresses in Cloud Atlas, Alec Guinness plays several roles in Kind Hearts and Coronets. In fact, he plays a total of eight characters, that is pretty amazing. One of the characters is the Lady Agatha D’Ascoyne. This comedic film made its debut in 1949, and may have helped inspire the hodgepodge of roles in Cloud Atlas. Alec Guinness’ portrayal of a female character is definitely at odds with his later role as the world-renowned character, Obi-Wan Kenobi. The portrayal of a man playing a women might be a big reason as to why the movie received an 8.2 rating on imdb.com.
9 Michael J. Fox – Back to the Future
Michael J. Fox was able to nail, not only one, but several roles in the iconic film Back to the Future. One of his most notable portrayals is of Marty McFly’s sister, Marlene. Although it’s slightly off-putting that Marlene and Marty look so similar, it certainly adds a comedic effect. Marlene’s futuristic getup and fabulous makeup help mask the fact that she is really played by a man. Although his part as Marlene is relatively small, we have to admit that Michael J. Fox makes a pretty hot girl.
8 Amanda Bynes – She’s the Man
Although she seems to have completely lost her mind today, Amanda Bynes wasn't always perceived as the actress who went off the rails. In fact, she used to be quite popular. Bynes showed her versatility in She’s the Man – not only does she play her own character, Viola, but she also pretends to be Viola’s brother. She’s the Man takes a leaf out of Back to the Future’s book, although Bynes’ Viola is only pretending to be her brother while Michael J. Fox actually plays his main character’s sister. Bynes wears a short wig and walks with a swagger to complete her role as Sebastian. While we have a hard time believing Bynes’ pretty face could be masculine, she’s hilarious in this coming-of-age film.
7 John Travolta – Hairspray
A man traditionally plays the role of female Edna Turnblad, and the 2007 remake of Hairspray conformed to this tradition. This time around, it was John Travolta who assumed the brilliant role of Edna, the main character’s mother. Travolta managed to fit the role by wearing a pink dress that was absolutely covered in sequins, and spent a lot of time in the makeup chair to prepare for the role. Although Travolta is often known for being a ‘man’s man,’ he certainly showed his versatility when he showcased his very feminine side in Hairspray.
6 Gwyneth Paltrow – Shakespeare in Love
Gwyneth Paltrow won the Academy Award for Best Actress for her amazing role in the 1998 film, Shakespeare in Love. Although Paltrow plays the female Viola, for the majority of the film, conventions are turned on their heads when she proceeds to disguise herself as a man in order to audition for the role of Romeo in Romeo and Juliet. In Shakespeare’s time, men usually played women’s roles, but Viola bravely resists the dismissal of women. Complete with a short wig, facial hair and an awkward goatee, Paltrow nails the role of Thomas.
5 Robin Williams – Mrs. Doubtfire
Although the late, great Robin Williams’ character as Mrs. Doubtfire, in the iconic film of the same name was only pretending to be a woman, he deserves his place on this list, simply due to his incredible acting. Williams as Mrs. Doubtfire made us laugh, made us cry, and made us all wish he was our dad. The film won the Academy Award for Best Makeup, which isn't surprising considering how well Williams was able to pull off the female role. Sadly, after Williams’ death, we’ll never get to see Mrs. Doubtfire 2, which was in the works.
4 Tilda Swinton – Orlando
Coming in at number 4 on this list is a character from the same film as the first entry. Orlando, based off of the novel by Virginia Woolf, tells the story of a man who lives for hundreds of years and wakes one morning to find out that he has become a woman. Tilda Swinton’s portrayal of the title character as both male and female is absolutely stunning. After viewing Swinton on stage in a different male/female role, the casting director immediately knew that Swinton was also the perfect choice to portray Orlando.
3 Cate Blanchett – I’m Not There
In the 2007 film based on Bob Dylan’s life entitled I’m Not There, Cate Blanchett plays a personification of Bob Dylan called Jude Quinn. Blanchett’s Quinn was meant to represent Dylan as he was around in 1965, and nobody could have done it better. Critics everywhere praised Blanchett’s performance as surreal and compelling, and she even received the Golden Globe Award and a nomination from the Academy Award, for Best Supporting Actress. Blanchett later claimed that stuffing a sock down her pants was an integral part when preparing for the role.
2 Hilary Swank – Boys Don’t Cry
In the 1999 film, Boys Don’t Cry, Hilary Swank perfectly captures the role of trans teenager Brandon Teena. Actually, stating that she captured the role would probably be an under-statement for the young actress. With regards to gender, this film is one of the most interesting on this list because it fully explores the construction of gender roles and the role of biological sex. Swank fully committed to her role: she cut her hair, shrunk down to 7% body fat, and lived as a man for a full month to really get into character. Swank’s performance earned her the Academy Award for Best Actress and countless other accolades. It certainly also paved the road for her future successes.
1 Linda Hunt – The Year of Living Dangerously
Linda Hunt’s portrayal of Billy Kwan in 1982’s The Year of Living Dangerously was so astounding that she gracefully received the Academy Award for Best Supporting Actress. Additionally, Hunt was the first person to receive an Academy Award for portraying a character of a gender different to her own. In order to appear as a male Chinese-Australian photographer, Hunt decided to chop off her hair and dyed it black, she padded her waist, and she even shaved off all of her eyebrows. Having a woman play the male character added extra layers of complexity to the film.