Glenn Close was nominated for an Oscar for her role as Albert Nobbs in the 2011 film of the same name. The film is based on George Moore’s novella The Singular Life of Albert Nobbs. Albert Nobbs is the story about a woman who chose to live as a man to survive harsh 19th century Dublin. On top of starring in the film, Glenn Close also co-wrote and produced it.
Albert Nobbs isn’t the first film where Glenn Close played the opposite gender. She had a brief cameo in Steven Spielberg’s 1991 film Hook as Gutless the pirate.
Meryl Streep was almost unrecognizable as the elderly Rabbi Isidor Chemelwitz in the HBO series Angels in America. For most of the series she played Ethel Rosenberg, the same Rosenberg who was executed in 1953 for conspiracy to commit espionage against the United States. But, her brief role as the Rabbi was impeccable. You can watch her amazing transformation in a scene from the show here.
Cillian Murphy makes such a pretty woman he’s played one twice. In the 2010 Peacock, Murphy plays John Skillpa, a man who suffers in secrecy from multiple personality disorder. His alter-ego is Emma, who does all the chores around his house. After an accident, Emma is revealed to his neighbors and believe that Emma must be John’s wife, and John struggles to keep up the charade.
In the 2005 film Breakfast on Pluto, Murphy played a transgender woman named Kitten.
Eddie Murphy is known for playing several characters in the same movie, and a good chunk of those characters have been female. In The Nutty Professor (1996), Eddie Murphy played both Sherman Klump’s mother and grandmother. In Norbit (2007), Eddie Murphy plays his own title character’s wife, a mean obese woman named Rasputia.
In the 2011 film Jack and Jill, Adam Sandler plays both title characters. Jack and Jill are fraternal twins who couldn’t be more opposite. Jill is a ne’er do well who has lived her entire life at home with their mother and Jack is her successful advertising exec brother who lives with his beautiful family in Los Angeles. The film is about Jack returning home for the holidays. While the movie got a whole bunch of Razzie awards, some think it’s underrated. The movie also featured Al Pacino in a strangely prominent role.
Tyler Perry is Madea. He made up the character years ago and first introduced her in his 2005 film, The Diary of a Mad Black Woman. Since then, Madea has been a character in over 10 Tyler Perry films. He said that the character is a mix between his aunt and mother and Eddie Murphy’s female characters in The Nutty Professor.
In Todd Haynes’ 2007 film I’m Not There, Bob Dylan’s life is personified by six distinct characters. Cate Blanchett’s portrayal of Dylan was so spot on that she received an Oscar nomination. Some of Dylan’s other incarnations were played by Ben Winshaw, Richard Gere, Heath Ledger and Christian Bale.
Angelina’s transformation into a male naval officer for her 2010 film Salt took several hours. She said that when her family came to visit her on set her then husband, Brad Pitt, refused to kiss her and her own children didn’t recognize her.
Hilary Swank won her first Academy Award for her harrowing portrayal of Brandon Teena in the 2000 film, Boys Don’t Cry. The film was based on the real-life 1993 rape and murder of transgender man Brandon Teena in Humboldt, Neb. To prepare for the role, Hilary Swank lived her life as a male for four weeks.
The 2015 film The Danish Girl was inspired by the true story of Lily Elbe, one of the world’s first recipients of gender-reassignment surgery. In the film Eddie Redmayne’s character was introduced to the audience as Danish landscape painter Einar Wegener. But after a model showed up for his painter wife, played by Alicia Vikander, Einar dressed up in women’s clothing. After that moment, Einar could not hold back his hidden desire to become a woman, and we watched as he began his full transition.
Dustin Hoffman may not make the most attractive woman, but he sure made a sassy one. In the 1982 film Tootsie, Hoffman plays an unsuccessful actor who is out of options and decides to try his luck auditioning for a soap opera role as a woman named Dorothy Michaels. He gets hired and quickly becomes America’s daytime sweetheart, but also finds himself tremendously over his head when he falls in love with the soap opera’s beautiful lead actress, played by Jessica Lange.
Katharine Hepburn was far ahead of her time. While most of the actresses of her time where wearing dresses, Katharine Hepburn was wearing menswear-inspired trousers and suits. So, it’s not all too surprising that Katharine Hepburn got in drag for a film while most of the other leading ladies of her time where glamour goddesses and bombshells. In the 1935 film Sylvia Scarlett, Hepburn dressed as a man while hiding out from the police.
In the 1982 Victor/Victoria, Julie Andrews plays a woman, playing a man, playing a woman. That’s really not as confusing as it sounds. In the film, Andrews plays a broke singer who with the help of her gay friend Toddy, decides that her spectacular voice would be a sensation if people thought it was a female-impersonator’s falsetto. So, Victoria ends up playing Victor, who plays Victoria.
15. Tony Curtis And Jack Lemmon In 'Some Like It Hot'
In the 1959 film Some Like It Hot, Jack Lemmon and Tony Curtis play two poor musicians who go into hiding within an all-female orchestra after they witness the St. Valentine’s Day Massacre. The two funny men play opposite the smoldering Marilyn Monroe. The film was ahead of its time in the way that it played with sexual identity films. Even Lemmon and Curtis said that they fought to get better dresses (Monroe’s equivalent) for their female personas in the film. There was also a funny moment when dress designer Orry-Kelly was taking Lemmon, Curtis and Monroe’s measurements. He had measured the men and went to measure Marilyn. Orry-Kelly said, “You know Marilyn, Tony Curtis has a better-looking a** than you.” Then supposedly Marilyn unbuttoned and opened her blouse saying, “He doesn’t have t*ts like these!”