It seems strange to think now, but centuries ago the stage was deemed an inappropriate place for a woman. As a result of the exclusion, it was the norm for men to play females in theater productions in what is called cross-gender acting. The convention reaches back to ancient Greek times, and was also prevalent in Japanese kabuki theater, as well as English renaissance theater.
Cross-gender acting differs from acting in drag or portraying a transgender or cross-dressing character, in that it is simply an actor authentically playing a character that happens to be of the opposite gender.
In modern times, despite the fact that there's really no need for cross-gender acting, it still occassionally occurs in film and TV, whether due to tradition, necessity or simply because the actor — regardless of gender — was the right fit for the part. However, unlike centuries ago, now it's acceptable for females to play male roles as well.
Below I've collected a bunch of examples of cross-gender acting in modern film and television. And while you may already be aware of some of the example, at least a couple may just surprise you:
1. Nancy Cartwright as Bart Simpson (among others), The Simpsons
Though she originally read for the part of Lisa Simpson, Nancy Cartwright ultimately ended up with the role of her trouble-making brother, Bart. Along with Bart, Cartwright also voices Nelson Muntz, Ralph Wiggum, Todd Flanders, Kearney and Database in the series.
It's not uncommon for women to voice pre-pubescent male characters in animation, given that if boys were to voice them, eventually they would age out of the role. Despite this, when The Simpsons first became a hit in 1990, Fox ordered Cartwright not to give interviews so not to reveal that a woman voiced Bart.
2. Cate Blanchett as Jude Quinn, I'm Not There
Cate Blanchett played a male character in the 2007 film I'm Not There. Blanchett played the character, Jude Quinn, one of seven different characters inspired by musician, Bob Dylan. Blanchett was the only woman to portray Quinn/Dylan, with the other characters being played by five male actors, but it was her performance that was praised by critics. For her part she won the Golden Globe for Best Supporting Actress as well as receiving an Academy Award nomination in the same category.
3. Brad Bird as Edna Mode, The Incredibles
Edna Mode only appeared briefly in The Incredibles, but in that short appearance managed to immortalize her costume-making manta, "no capes!" But while Edna might be a world-famous seamstress in The Incredibles universe, in reality she was voiced by the male director of the film, Brad Bird!
Originally the director intended for Lily Tomlin to voice the character, but when he demonstrated the type of voice he wanted, Tomlin suggested that he perform the voice instead, thinking she wouldn't be able to make the character as funny as Bird. Interestingly, Edna is voiced by a mixture of female and male voice actors in the various different language versions of The Incredibles.
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4. Meryl Streep as rabbi Isidor Chemelwitz, Angels in America
The rabbi in Angels in America features only briefly at the very beginning of this 2003 mini-series, which is perhaps why you might not have noticed that he's actually played by Meryl Streep.
In total Streep actually had four roles in the mini-series, also playing Hannah Pitt, Ethel Rosenberg and The Angel Australia. This was in keeping with the play that the mini series was based on, Angels in America: A Gay Fantasia on National Themes. Playwright Tony Kushner wrote the play for eight actors, with all playing two or more roles, and several of the roles requiring actors to play the opposite sex. While the mini-series had actors Jeffrey Wright and Emma Thompson also playing more than one role, Streep was the only one of the three to play a character of the opposite gender.
5. Rupert Everett as Camilla Fritton, St Trinian's
This is an interesting cross-gender role, that actually has roots in the original St Trinian's film franchise.
In the original 1954 film, The Belles of St Trinian's, Alastair Sim had already signed on to play the role of Clarence Fritton when Margaret Rutherford, the actress set to play his sister, Millicent Fritton, became unavailable. After the director and co-producer were unable to find a suitable actress to replace her, Sim agreed to play both Fritton siblings himself.
When the series was rebooted with St Trinian's in 2007, the tradition Alastair Sims inadvertently started was continued when Rupert Everett took on the roles of both Camilla and Carnaby Fritton (the 2007 versions of Millicent and Clarence).
6. Glenn Close as Gutless, Hook
This cross-gender role was so convincing that when the film was released most people had no idea Glenn Close was even in the film, let alone played a male pirate.
Apparently Close ended up appearing as a featured extra in the film because she was on set visiting her friend, Dustin Hoffman, when he asked her if she wanted to star in the scene they were shooting. After going through the makeup process (sprouting a beard in the process!), Close became Gutless the pirate, and appeared in the infamous "boo box" scene in Hook.
7. John Travolta as Edna Turnblad, Hairspray
Much like the St Trinian's example, the role of Hairspray's Edna Turnblad being played by a man has become tradition.
In the original 1988 version of Hairspray, Edna Turnblad was played by drag queen, Divine. The role was given to Divine by the director and writer of the film, John Waters, who was Divine's long-time friend and collaborator. When the film was made into a Broadway musical in 2002 the tradition of casting a male as Edna Turnblad was maintained when Harvey Fierstein was cast in the role. Most recently John Travolta took over the role in the 2007 adaptation.
Despite the fact that Divine was a drag queen, he later noted that with the role of Edna Turnblad he could not be considered a drag queen, once saying "what drag queen would allow herself to look like this? I look like half the women from Baltimore."