As people say, there is no business like show business. Undoubtedly, the film industry is one of the most interesting fields. Young actors steal the spotlight from adults, adult actors are cast as teenagers, and male actors are cast as females and vice versa.
Immersing oneself in a character of the opposite gender, whether it is a man playing a woman or a woman playing a man, sounds like a great way to start understanding the other side of our duality. And actors who portray gender-transitioning characters add to our understanding of gender and our humanity. Or, at least that is what happens when the actors perform it well. Any woman can parade around a movie set with a sock in her pants, and any man can put on makeup and go have a gossip meeting in a salon.
Here are the 15 actors who played the opposite gender, as interesting as that may sound.
#1 Adam Sandler (Jack and Jill)
The world was treated to one of the worst films ever made as well as a double performance by faded comedian Adam Sandler as fraternal twins Jack and Jill Sadelstein.
Amazingly, not even co-stars Katie Holmes and Al Pacino could have prevented the film from receiving dozens of strongly negative reviews with a performance as bad as the films.
#2 Amanda Bynes (She’s The Man)
Source: Flare Magazine
Viola Hastings, played by Amanda Bynes, is desperate to join the school’s soccer team because she loves football, but there is only one issue: boys only. The teen impersonates her brother because she is determined to make the team and succeeds in her goal of joining it.
The film is a ton of fun to watch, but it now serves as a somber reminder of how the stunning Bynes’ career might have reached incredible heights if she hadn’t been involved in legal matters involving DUI, reckless driving, criminal marijuana possession, etc.
#3 Angelina Jolie (Salt)
Source: KAZU HIRO
The actress doesn’t rely on her appearance to gain fame; instead, she has extraordinary acting talent, as evidenced by several of her acting roles, which are typically played by male actors.
In the 2010 film Salt, where she played a man disguised as a woman, Jolie was barely recognizable thanks to hours of makeup and numerous prosthetics.
#4 Cate Blanchett (I’m Not There)
When the biopic I’m Not There about Bob Dylan, one of the most influential musicians of all time, was announced, everyone was curious about who would play the lead role. Unexpectedly, seven different actors were chosen to represent various facets of the singer’s life.
Interestingly, Cate Blanchett, a female actor, was one of them. She astonishingly resembled Dylan and demonstrated that sometimes a woman can perform a man’s job much better.
#5 Charlie Chaplin (A Busy Day)
Charlie Chaplin was quite a handsome man in his heyday. It really says a lot about the Hollywood legend who may have been the first actor to play the opposite sex in a film to have multiple alleged affairs and four marriages.
Chaplin uses a dress and other props to portray a plain-appearing wife in the short film A Busy Day who develops jealousy when her husband expresses interest in another woman. Even though it only lasts for six minutes, it is entertaining to see the renowned actor in a different role than the awkward tramp.
#6 Dustin Hoffman (Tootsie)
In his long career, Oscar-winning actor Dustin Hoffman has earned a reputation for his versatility, and the 1982 comedy Tootsie is a prime example of this. The actor played Michael Dorsey, a perfectionist actor who no one wants to work with.
When Dorsey realized that his tough reputation might mean the end of his career, he changed his appearance and adopted the name, Dorothy Michaels. He is surprised to see a resurgence in his professional life.
#7 Eddie Redmayne (The Danish Girl)
The lead part in the biopic of Lili Elbe, one of the earliest known patients of sex reassignment surgery, was offered to Eddie Redmayne. Redmayne accepted the challenge and received a second Academy Award nomination, but Leonardo DiCaprio ultimately won.
#8 Elle Fanning (About Ray)
The emotional drama film About Ray, which is directed by Gaby Dellal and stars Elle Fanning as Ray, is about Ray’s pursuit of her true identity as a man and her efforts to persuade her mother, grandfather, and absent father to accept it.
The director said, “The part is a girl and she is a girl who is presenting in a very ineffectual way as a boy.” Despite the film’s unfavorable reviews, the handsome Fanning played the part perfectly.
#9 Glenn Close (Albert Nobbs)
Close had to wear a lot of makeup and give it to her all to completely nail her performance as the male character Albert Nobbs in the same-named film. The actress was nominated for an Academy Award six times, but Meryl Streep won (who interestingly happens to be her look-alike).
#10 Gwyneth Paltrow (Shakespeare in Love)
Ben Affleck, Joseph Fiennes, and Geoffrey Rush’s male co-stars were overshadowed by actress Gwyneth Paltrow, who was nominated for 13 Academy Awards and took home seven of them, including Best Picture.
In Romeo and Juliet, the most well-known play by Shakespeare, Viola de Lesseps plays an actress who poses as a man to appear in an audition as Romeo. Paltrow’s commitment paid off when she won the Academy Award for Best Actress for the role, despite sporting facial hair, short hair, and even a goatee.
#11 Hilary Swank (Brandon Teena)
To prepare for her transgender Brandon Teena role in Boys Don’t Cry, Hilary Swank spent a full month living as a man. The actress went so far as to introduce herself to family and friends as her brother James, along with having her hair cut short, her breasts bound, and a sock hidden in her underwear.
Her dedication paid off when she gave a powerful performance that left everyone who saw the movie in tears, winning her the Academy Award for Best Actress.
#12 Jared Leto (Dallas Buyers Club)
Source: The New York Times
The rock band 30 Seconds to Mars frontman has performed a role that required the opposite sex, just like every other entry on the list. Then, Leto was honored with the Best Supporting Actress Oscar for the performance. The actor, who portrays Rayon, a transgender woman in Dallas Buyers Club, has garnered praise from both audiences and critics.
#13 John Travolta (Hairspray)
Amazingly, the actor who played a hitman in Pulp Fiction and an FBI agent in Face/Off would one day take on a female role! John Travolta starred as the obese Edna Turnblad in the musical comedy Hairspray in 2007.
Although celebrities like Steve Martin, Tom Hanks, and Robin Williams were also considered for the part—to say the least, it was not a pretty sight—producers Craig Zadan and Neil Meron actively pursued Travolta to take it.
#14 Martin Lawrence (Big Momma’s House)
Martin Lawrence played both an obese grandmother and an FBI agent in the movie Big Momma’s House, which required him to perform two roles. A woman and her son need the actor’s protection as Big Momma against a thief. The comedy film received criticism despite having some funny moments. Lawrence played the character again in two sequels despite this fact.
#15 Robin Williams (Mrs. Doubtfire)
Through his fascinating performances, including Mrs. Doubtfire in the 1993 comedy-drama film of the same name, the late Robin Williams will live on forever. As Daniel Hillard, he would do anything to care for his children who had moved out after a contentious divorce.
Hillard gets a second chance to prove his abilities as a husband and father by dressing as a woman and posing as a nanny named Euphegenia Doubtfire. As the film won an Academy Award for Best Makeup, Williams’ transformation into a woman was truly amazing.