Men playing the female parts in plays used to be a common practice. Even iconic female roles like Lady Macbeth, and Ophelia (from Shakespeare's, Hamlet) were played by male actors. In the early years of theater, women were not allowed to act, so unless a play didn't have any female parts, then it was up to the younger boy actors to put on a dress and do the best they could.
Voice acting is even more diverse, because all that matters is that the actor, or actress, can make their voice sound male or female, to fit with the character. For example, Nancy Cartwright has voiced Bart Simpson on The Simpsons for its entire 25 season run.
But when it comes to live action, female parts tend to go to, well, women. But, there are some actors out there who like a challenge. Or just enjoy wearing women's clothing. And who can blame them? So, which one of these actors who has played a female character on the big screen, do you think makes the most attractive woman?
9 Dustin Hoffman - Tootsie
In the critically and commercially successful 1982 film, Tootsie, Dustin Hoffman plays an actor who can't find a job because of his reputation for being difficult to work with. He decides to audition for a role in a soap opera by dressing up as a woman, and he lands the part. His character's popularity takes off, and he's stuck juggling his career as a woman, and his personal life as a man. His female persona, Dorothy, has to fight off multiple advances from men, and invent wild stories to cover up the fact that she is really a man. The film won a total of ten Academy Awards, and in 2000, the American Film Institute ranked Tootsie as the second funniest film of all time.
8 Rupert Everett - St Trinian's
In the sixth installment of the UK film series, Rupert Everett plays the part of Miss Camilla Dagey Fritton, the eccentric headmistress of boarding school for girls, St. Trinian's. The series is based on the works of cartoonist, Ronald Searle, with the first one being released in 1954, and sequels following in 1957, 1960, 1966, and 1980. Casting a male actor in the female headmistress role was a staple of the series from the beginning, with actor, Alistair Sim playing Miss Fritton in the first 5 films. The 2007 film was intended as more of a series reboot, than a sequel.
7 Michael J. Fox - Back to the Future Part II
In this star-making 80's classic, Michael J. Fox plays the main character, Marty McFly. He travels forward in time using a DeLorean as a time machine and meets his future twins, Marty Jr. and Marlene McFly, who are both portrayed by Fox. Not only did Fox play multiple characters in the same film, but he had to act opposite himself in a lot of scenes. The film was nominated for visual effects awards because of the development of a new computer-controlled camera system, called VistaGlide, which was invented specifically to enable one actor to play multiple characters in the same scene.
6 John Travolta - Hairspray
5 Martin Lawrence - Big Momma's House
Dressing up as an elderly lady named Big Momma is the perfect cover for an FBI agent who is looking for an escaped convict. Martin Lawrence plays master of disguise and FBI agent, Malcolm Turner in 2000 comedy, Big Momma's House. In it, he takes over a suspect's grandmother's identity in order to trick the suspect into a confession. Malcolm has to successfully impersonate Big Momma, while maintaining his professionalism and focusing on solving the case. He may look like Big Momma, but he can't fake her cooking skills, and grandmotherly affection quite as convincingly.
4 Robin Williams - Mrs. Doubtfire
The 1993 film, Mrs. Doubtfire won an Academy Award for Best Makeup for accomplishing the difficult task of transforming Robin Williams into a woman. In the movie, Robin Williams' character Daniel, is in the process of a divorce and doesn't get to see his kids as much as he'd like. So, he decides to dress up as a woman and apply to be their nanny. Mrs. Doubtfire, an elderly woman with a strange amount of energy is the result. As of April 2014, a sequel to the film is in the works, with Williams returning as the title character.
3 Adam Sandler - Jack and Jill
2 Eddie Murphy - The Nutty Professor
The king of playing multiple characters in one movie, and often one scene, is Eddie Murphy for his portrayal of the entire Klump family in The Nutty Professor, and its sequels. Murphy goes through a lot of transformations for the film, especially when he plays members of the main character's family, The Klumps. In one scene he plays 5 different characters all sitting around the dinner table. He dresses up as two different women to play Mama Anna Klump, and Grandma Klump. The film also won an Academy Award for Best Makeup.
1 Tyler Perry - Madea Goes to Jail
Most people know director, Tyler Perry, better as his signature character, Madea. Perry has written, directed, and starred in multiple films featuring Madea, including Madea Goes to Jail, Madea's Family Reunion, and A Madea Christmas. She made her first appearance in the 1999 play, I Can Do Bad All By Myself, and her popularity took off from there. Entertainment Weekly included Madea on an end-of-decade best-of list, saying she is "the profane gun-toting granny, you never had, but (maybe) wish you did"