Have you ever heard of the term ‘cross-gender acting?’ It’s when an actor or actress plays a character of the opposite sex. It’s actually been around for thousands of years. But it doesn’t only exist in Shakespearean plays and movies based in that period (while some actually do, though). Most of the modern examples of cross-gender acting are in serious movies with really well-played performances like Tilda Swinton, who’s played a man in more than one movie.
And then there are the less serious and let’s say… less well-played roles, like the Wayans Brothers in White Chicks who are playing not only another gender but another race! But we’ll get to that. While some actors and actresses pull it off almost too well, others are so clearly not convincing, and it really only distracts us from the movie’s plot. These are the actors and actresses who took the challenge and played the opposite gender. You can be the judge as to who played it well or not.
Cate Blanchett in I’m Not There (2007)
Cate Blanchett is one of those chameleon actresses who seems to be able to play pretty much any role. Case in point: her role as Jude Quinn, a personification of Bob Dylan, in the 2007 biopic I’m Not There. Bob Dylan is played by a total of six actors in the film, including Christian Bale and the late Heath Ledger. Each one represents a different side of the legendary singer.
Blanchett is totally transformed, from head to toe – from her refined, elegant self into a scruffy 60s star. Director Todd Haynes insisted that she wear a suit exactly like the one Dylan wore in 1965. It’s hard to imagine anyone else do a more compelling and surreal performance. She won the Oscar for Best Actress in a Supporting Role. So, yeah, she pulled it off.
Michael J. Fox in Back to the Future Part II (1989)
This list can’t be all serious like I mentioned before. So, here’s an example of a rather comical cross-gender role. And I gotta admit, I completely forgot that Michael J. Fox played a woman in this sequel of the 80s cult classic. In the sequel, Fox plays a number of characters, including Marty McFly, Marty Jr. and, Marlene McFly (Marty McFly’s daughter).
And let’s all admit that he played a pretty good-looking daughter, too. The movie came out in 1989, which was only two years before he was diagnosed with Parkinson’s in 1991. Fox kept it a secret from the public until 1998. Then, as you know, he became an advocate for finding a cure. He founded the Michael J. Fox Foundation in 2000.
Angelina Jolie in Salt (2010)
Arguably one of the most beautiful actresses of our time, Angelina Jolie, clearly has the confidence to lose the femininity and her inherent sexiness to challenge herself with a role like this. She slipped out of her regular self and transformed into a man in the movie Salt. She had pounds of prosthetics and makeup slapped on her every day of shooting.
The result? A dapper man in uniform, which was actually a cameo written for a man. The role may not qualify as a legitimate cross-gender role because the character is disguising herself as a man, but still. She does it well. Jolie went as far as covering her entire face in latex – with fake ears, a fake nose, and a completely fake neck. Even her own husband (yes, Brad Pitt) and children couldn’t recognize her when they visited her on set.
Dustin Hoffman in Tootsie (1982)
Tootsie is a movie in which a talented actor, Dustin Hoffman, played a female role and turned himself into a woman with the right clothes and makeup. Hoffman was nominated for the Oscar for Best Actor that year due to his incredible and memorable performance. It might have been the most famous cross-dressing performance of all-time.
Hoffman put on the big hair and the big glasses and stepped into the high heels of a working girl called Tootsie. He put a lot of detail into everything, from the outfits he wears to the sweet and yet judgmental tone of Tootsie’s southern accent. If you haven’t seen this movie yet, you should put it on your list of old movies to see soon.
Glenn Close in Albert Nobbs (2011)
Glenn Close played the role of Albert Nobbs in the movie of the same title. Close played more than one role in the film and was co-writer and producer. This woman is clearly talented and knows how to do multitasking better than anyone. Close said in an interview that the movie is more than gender roles, it’s “about how people survive and about how human beings need to feel safe.”
The movie tells the story of Albert Nobbs, someone who was born a woman but lived her life as a man for 30 years. Why? To gain independence. In this image, the main character is female, as is the actress portraying her. The film got mixed reviews, but Close’s performance raised no questions. She earned the nomination for the Academy Award for Best Actress.
Cillian Murphy in Breakfast on Pluto (2005)
Another unexpected transformation took place in the film Breakfast on Pluto, where Cillian Murphy, who normally has a masculine aura and a deep voice, played a transgender orphan named ‘Kitten.’ The film is about a young transgender in the 1970s. After being at birth, she’s trying to find her mother.
The sweet character of Patrick “Kitten” Braden was so far removed from real-life Murphy, in terms of personality, which proves how much of a challenge this was for him as an actor. In order to get an understanding and properly prepare for such a part, Murphy mentioned how he went to transsexual clubs and spent time talking and just being around transgender people. It clearly helped him pull the role off.
Hugo Weaving in Cloud Atlas (2012)
A far cry from his iconic role as Agent Smith in the Matrix films, Hugo Weaving, took his acting in another direction completely when he signed on for the movie Cloud Atlas. He actually played several roles, like most of the actors in the movie. And most of the roles lay outside the gender or race norms.
Hugo’s most memorable character in this movie was Nurse Noakes, a vicious woman who was ugly on the outside and was even uglier on the inside. The brilliant actor left the audience in awe as he hilariously portrayed a jailer-nurse in a retirement home, which is pretty much a prison. Weaving’s tall and masculine figure put into a nurse’s uniform was, at the same time, absurd and genius.
Hilary Swank in Boys Don’t Cry (1999)
The beautiful Hilary Swank had no problem chopping off her long brown hair to play Brandon Teena in Boys Don’t Cry, a movie that was exploring gender roles long before it became a thing. The film, by the way, was based on a true story. To prepare for the role, Swank lived a month as a man.
This list wouldn’t be complete without the mention of Swank’s Oscar-worthy portrayal of a girl who was born Teena Brandon and becomes the male version of himself – Brandon Teena. The film was dramatic and pretty much-touched anyone who saw it. In an interview, Swank said cutting her hair was the first step for the role and then trying to come across as a boy on the street.
Jared Leto in Dallas Buyers Club (2013)
This role turned out to be one of the more controversial ones because Jared Leto actually won the Oscar for it. The problem for those people who protested the decision to even cast Leto for the role was that it should have been given to an actual transsexual instead. They may have a point, but one thing is for sure: he made an amazing transformation for his part in Dallas Buyers Club.
According to Leto’s recollection of the experience, he stayed in character throughout the entire shoot. He’s one of the many method actors that take their roles to the extreme. He also lost over 40 lbs in order to dramatically alter his body and, in his own words, to “change the way he felt others treated him.”
John Travolta in Hairspray (2007)
John Travolta has made his mark in Hollywood, and it’s generally a masculine one (despite the tight leather pants and all the musicals). In Hairspray, he switched things up and played the character of Edna Turnblad. Just like how a woman is typically cast for the role of Peter Pan, Edna is traditionally played by a male actor. The 1988 version also had an actor play the part (which we’ll get to later on).
In the lighthearted and feel-good musical, Travolta wore a 30-pound fat suit, a wig, and high heels to become the work-from-home mom, Edna Turnblad. Makeup artists had to work on him for 5 hours each day before filming. Travolta mentioned in different interviews that he truly had fun with the role.
Quentin Crisp in Orlando (1992)
The role of Queen Elizabeth I seems to be a popular one in movies and on TV. The 1992 film, Orlando, with Tilda Swinton (she’s next on the list) travels across time and gender. The film won a number of awards and was even for an Oscar, but people overlooked Quentin Crisp’s (an English author and illustrator) role as Queen Elizabeth I. take a second to look at him as the Queen.
He was 83 when he was asked to play Queen Elizabeth I, who was meant to be at the age of 67. Crisp later spoke about how kind and helpful everyone was on set, but he still described it all as being “absolute hell.” The worst part for him was wearing the costume, which was made of different, highly uncomfortable pieces that left blisters on his body.
Tilda Swinton as Orlando (1992)
Since we’re already on the topic of Orlando, this is one of Tilda Swinton’s first major transformations on screen. The movie’s director, Sally Potter, said that seeing Swinton in a play, seeing a “profound subtlety about the way she took on male body language and handled maleness and femaleness.” In this film, Swinton played Orlando himself. And just by looking at Swinton, it really doesn’t surprise me that she plays such roles. She has the face for it.
Orlando was a young nobleman commanded by the Queen to stay young. Throughout the movie, Orlando goes through several eras, even changing her gender in the process. Swinton recently played another male role in the movie Suspiria as Dr. Josef Klemperer. We’ll get to that later on, too.
Tom Hanks – Bosom Buddies (1980-1982)
Who here remember the show Bosom Buddies? The cross-dressing comedy was Tom Hanks’ big break. Before its premiere in 1980, Hanks had one TV credit on his resume which was an appearance on The Love Boat. Paired with Peter Scolari, Hanks turned a risky premise into a beloved sitcom. And the cross-dressing concept something of a happy accident.
Creators Thomas Miller and Robert Boyett pitched the idea to the network, which was to be a male spin on the network’s hit show, Laverne & Shirley. They referenced Billy Wilder as their influence, the man behind the classic movie Some Like It Hot. The executives loved it and, remembering Jack Lemmon and Tony Curtis in drag went with it. Miller and Boyett went along too, even though the cross-dressing wasn’t their original intention.
Eddie Redmayne in The Danish Girl (2015)
Only six months after winning the best-actor Oscar for playing another real-life figure, Stephen Hawking, in The Theory of Everything, eyes were back on Redmayne. He played Einar Wegener/Lili Elbe – one of the first-ever people to undergo sex-change surgery. He was helped in his preparation for the role by Lana Wachowski, who “guided him towards the books that would help him understand and sink into his character.”
Redmayne basically studied Lili Elbe’s pseudo-autobiography called “Man Into Woman,” and studied sketches of her. He read other books by and about her as well as meeting six transgender women from different generations to learn their experiences. “Their openness of spirit was unlike anything I’d ever seen,” Redmayne said. “That was galvanizing — you felt the trust.”
Johnny Depp – Ed Wood (1994)
Johnny Depp is known for playing the weirdo in many of his movies, but this one is lesser-known for some reason. He played the cross-dressing director, Ed wood, who is known for being the worst director of all time. Depp in Tim Burton’s black and white film was less terrible than the character he was playing.
Wood has more than just an endless enthusiasm for directing movies. He also has a desire to dress up in women’s clothing. He specifically likes angora sweaters. Depp was all game as the cross-dressing director, and at times took his performance right up to the edge but never crossed it. What do you think of Depp as a woman? Believable? I personally don’t buy it.
Tony Curtis and Jack Lemmon in Some Like it Hot (1959)
Everyone loved watching two loser musicians who were forced to pretend to be women in this classic movie. The late Jack Lemmon got an Oscar nomination for his role and won a Golden Globe. Some Like It Hot is frequently included in lists of the best films ever made, and it was also one of the first times that audiences saw men dressed in drag on the screen.
Billy Wilder’s comedy has one of the best closing lines in cinema. Lemmon tore off the wig he’s been wearing for most of the movie and declares, “I’m a man!” Then, Joe E. Brown, the millionaire who fell in love with him/her, calmly responds by saying, “Nobody’s perfect.” Lemmon’s character reveled in the role of playing a woman. But Curtis’ was stumbling, barely covering his masculinity, which worked perfectly next to Lemmon’s girlishness.
Marlon and Shawn Wayans in White Chicks (2004)
Keep in mind that this movie came out in 2004, before today’s over-sensitive climate. I can only imagine what would happen if this was released today. Anyway, when Marlon and Shawn Wayans chose to play FBI agents who pose as the blond, blue-eyed Hilton sisters in White Chicks, they had no idea what they were getting into.
”I just thought it was a funny idea. I wasn’t even thinking about the makeup when we first came up with it,” Shawn explained. The funny idea turned into seven hours of makeup a day, tons of acrylic paint, and contact lenses that were so painful ”they should be the s— that they use over in Iraq to get information out of al-Qaeda,” Shawn said.
Amanda Bynes in She’s the Man (2006)
This teen comedy was an adaptation of Shakespeare’s play, Twelfth Night, which tells how hard it is to be two people at the same time. Amanda Bynes played both Viola and her twin brother Sebastian. But Bynes was nowhere near as fond of the film as her fans were. The now 33-year-old revealed in a story for Paper Magazine that her role as Viola had a negative effect on her mental health.
“When the movie came out, and I saw it, I went into a deep depression for four to six months because I didn’t like how I looked when I was a boy,” Bynes said. She said that watching herself onscreen with short hair, thick eyebrows, and sideburns was “a super strange and out-of-body experience.”
Louie Anderson in Baskets (2016 – 2019)
Of all the actors and actresses on this list, Louie Anderson’s role as Christine baskets has got to be my favorite. For anyone who knows of the comedian, it makes the character even more fun to watch because he pulls it off perfectly. He manages to play a mother, both hilariously and tragically, at the same time. It’s actually one of the most sympathetic and compelling portraits of motherhood on TV. Ironically, it’s done by a man.
Anderson even won an Emmy in 2016 for Supporting Actor in a Comedy Series. Anderson described channeling his own mother, Ora, for the role of Christine. She was a South Dakota native who spent most of her life in Minnesota. Anderson said that when he steps out of his trailer, it’s as if he opens up a channel to his mother (who passed away).
Tilda Swinton in Suspiria (2018)
Okay, stay with me on this one. The movie’s casting director said: “Tilda Swinton has played the role of Madame Blanc, while the character of Dr. Klemperer has been played by Professor Lutz Ebersdorf.” But that isn’t really the truth. Dr. Klemperer was actually played by Swinton, just with pounds of aging makeup. Ebersdorf doesn’t even exist. Swinton and Guadagnino (the director) came clean to The New York Times about their prank.
So why did they invent a fake elderly actor when it has nothing to do with the movie itself? Swinton said, “Undeniably, I would have to say, for the sheer sake of fun above all. As my grandmother would have it—a motto to live and die by—‘Dull Not To.’” She even had an Ebersdorf headshot taken for the “actor’s” fake IMDb page. IMDb has since removed the fake page, and if you search for his name, you’ll be directed to Swinton’s page.
Barbra Streisand in Yentl (1983)
Yentl was a pretty important film. Streisand didn’t only play the lead; she also wrote, produced, and directed it. It was her directorial debut that she won a Golden Globe for directing — and apparently, she’s the only woman who won the award since. In the film, she plays Yentl, a Jewish girl who defied all social and religious boundaries by taking the name of her brother, Ashnel, to be able to study.
Like her character, she said that she was struggling with gender bias when she was trying to get the movie made. She had to hide the fact that she co-wrote the script by not even putting her name on it at all. “I was afraid if they saw my name on it, [people in Hollywood] wouldn’t like it,” she later admitted.
Robin Williams in Mrs. Doubtfire (1993)
Not only do I want to include Robin Williams as an obvious member of this list, but I also like to find every opportunity to honor him. He will forever be missed as someone who can make anyone smile. Mrs. Doubtfire was itself a classic, and Williams’ role was iconic. How can anyone not find a desperate dad pretending to be an elderly woman just to be close to his children and wife not compelling?
Fun fact: did you know that the movie was based on the book “Madame Doubtfire?” It was a 1987 novel by a British children’s author named Anne Fine. The story was about a divorced man struggling to get access to his kids. Williams attached himself to the lead character, Daniel Hillard before he even saw the script.
Jude Law – Rage (2009)
I have to admit that before making this list, I never even heard of the movie Rage, let alone the fact that Jude Law played a drag queen called Minx. As a fan of Jude Law and his charming boyish looks, it is definitely strange to see him look like a convincing Russian woman in a wig and full makeup.
The movie follows a student filmmaker as he makes a documentary about the important people in New York’s City’s fashion scene. The little known film actually has an impressive cast, including Judi Dench, Steve Buscemi, and John Leguizamo. Makeup Artist Morag Ross was the man who turned Law into a lovely-ish lady. As for his eyelashes, nails, and cheekbones, credit goes to Jude Law himself for going all-natural.
Felicity Huffman in Transamerica (2005)
This is another one of the increasingly popular transsexual roles, but what we really have here is Felicity Huffman playing a man who’s transitioning into a woman. Huffman immersed herself into the world of transgender people, spending every spare minute of her time with research. It all earned her an Academy Award nomination and a Golden Globe-winning film.
You probably know about the whole college admissions scandal. Well, since her sentence of 250 community hours, Huffman has decided to turn over a new leaf and occupy herself with charity work, particularly for incarcerated women. Former inmate Susan Burton said, “She has connected with them in a real way, and you can feel it. I think that is because they know she’s experienced in a small way what they have gone through being incarcerated.”
Eddie Murphy in The Nutty Professor (1996)
I think it’s important to throw in the less serious, funnier, and even less compelling cross-gender acting performances. While Eddie Murphy’s characters in The Nutty Professor wasn’t the best performance of his career, it was pretty damn impressive. One of the highlights of the comedy is his characterizations of Mama and Grandma Klump, who make some brief appearances at the dinner table.
For 70 days of the production schedule, Murphy was in the makeup chair for 3 1/2 hours every morning and an additional hour at the end of the day for safe removal. “I love makeup,” the makeup artist Rick Baker says, “but even I wouldn’t want to sit in a chair for 70 days with people poking me in the face. Eddie was always in great spirits. The only thing he wouldn’t do was shave his mustache, which made the mother and the grandmother a bit more of a challenge. But all in all, he was a joy to work with.”
Rupert Everett in St Trinian’s (2007)
Rupert Everett took on the role of Camilla Fritton in the comedy, St Trinian’s. Everett has recently revealed that he was transgender in his childhood and dressed up as a girl from the age of 6 to 14. But the openly gay British actor, now 60, said that he decided he no longer wanted to be a woman.
“I really wanted to be a girl. Thank God the world of now wasn’t then, as I’d be on hormones and would be a woman. After I was 15, I never wanted to be a woman again.” He warns about the dangers of today’s youth having sex-change operations, saying those parents who “get medical” are scary. It is indeed scary and it’s good that celebrities like him are speaking up about it!
Adam Sandler in Jack & Jill (2011)
Jack and Jill is yet another (sorry to say, but) crappy romantic comedy. Only this one’s different because Sandler plays both Jack, a family man, and his twin sister Jill, who visits him for Thanksgiving and won’t leave. Steven Koren (who wrote Evan Almighty and Click) wrote the screenplay, and Dennis Dugan (Grown Ups, You Don’t Mess with the Zohan, The Benchwarmers) directed it.
Katie Holmes played Sandler’s wife, and even the legend himself, Al Pacino, made a cameo. But Sandler’s Jill wasn’t well-liked by many. According to NY Magazine, “His Jill is a whiny shrew, an underminer, with shoulders like a linebacker and a speech impediment that makes her sound like an idiot… The Anti-Defamation League should picket the movie for crimes against Jewish women. The Friars Club should picket it for crimes against comedy.”
Patrick Swayze in To Wong Foo Thanks for Everything, Julie Newmar (1995)
Patrick Swayze got a Golden Globe for Best Actor in this comedy, where he played the drag queen, Miss Vida Boheme. The director, Beeban Kidron, said in an interview long after that the first thing she remembers of her movie was wolf-whistling at Patrick Swayze and Wesley Snipes as they walked down a road in Nebraska, dressed in skirts and high heels.
“They were really kind of furious in the moment, and then we were all laughing.I just thought it was a really interesting gender moment,” she told Yahoo Movies. The late Patrick Swayze had his own makeup people who made him into a woman. He also insisted that he and Beeban walk around the city to prove that he could pass as a woman. And he did.
Alec Guinness in Kind Hearts and Coronets (1949)
Alec Guinness was one of those English theater actors, who went from Shakespearean plays to Hollywood blockbusters after World War II. Guinness had a way of bringing to life brought his characters both on stage and on screen, including his brief but memorable role as a woman named Lady Agatha D’Ascoyne in Kind Hearts and Coronets.
The 1949 comedy had him playing eight different characters, and Lady Agatha was one of them. This role was very different from his previous and following roles. It was even an inspiration for the later trend of men playing women, like in Cloud Atlas. Guinness passed away in 2000 at the age of 86. His last movie was Interview Day, which came out in 1996.
Linda Hunt in The Year of Living Dangerously (1982)
Linda Hunt played a Chinese-Australian dwarf named Billy Kwan, a photographer who paired up with foreign correspondent Guy Hamilton (played by Mel Gibson). Hunt is something of a little wonder woman is of only 1.45 meters height, but her powerful acting stands tall. Her voice has been heard in various documentaries, commercials, and cartoons.
In The Year of Living Dangerously, she chopped her off hair, dyed it black, shaved her eyebrows, and padded her waist. Her performance is startling because her performance is so good that the audience never stops to doubt it. She does it so convincingly that it’s a non-issue. Deservingly, she was the first woman honored with an Academy Award for playing a character of a different gender.
Divine in Hairspray (1988)
Remember when I said earlier that the role of Edna Turnblad in Hairspray was traditionally given to a man? Well, this is the original version of the movie from 1988. Divine (Harris Glenn Milstead) was better known by his stage name. He was an actor, singer, and drag queen. He easily took the role of Tracy’s concerned mother.
Sadly, Divine died in his sleep that same year, in 1988, in a hotel room at the age of 42. He was a favorite of his friend and director, John Waters when it came to casting him in his movies. Other than Edna, Divine also played Babs Johnson in Pink Flamingos, Dawn Davenport in Female Trouble, and Francine Fishpaw in Polyester.
David Duchovny in Twin Peaks (1990 – 1991)
Here’s another hidden gem that I was never aware of! You know him best as Fox Mulder in The X-Files and Hank Moody on Californication, but have you seen him as Denise Bryson on Twin Peaks? Denise Bryson (formerly Dennis Bryson) used to be a former DEA Special Agent. She later became the FBI’s Chief of Staff.
Duchovny even reprised his role in the remake of the show Twin Peaks: The Return. The show was meant to be a mix of melodrama, comedy, horror, thriller, and pretty much every genre imaginable. In the remake, Denise made a quick cameo as the now the FBI Chief of Staff. It shows us that being transgender wasn’t an obstacle in progressing in her career.
Woody Harrelson in Anger Management (2003)
Anger Management was a movie with Adam Sandler as David Buznik. Sandler’s films are known for their offensive characters, but it’s usually Sandler himself who wears the wigs and talks with the accents. But this time, he had Woody Harrelson play a transvestite German prostitute. Having Harrelson slap Sandler in the face repeatedly didn’t make up for the fact that his role was just a big joke.
It’s funny such a small part in a movie and can be so memorable. People really took to Harrelson’s Galaxia, which was seen as both disturbing yet captivating. Harrelson is 58 now, and his latest film, Zombieland: Double Tap recently came out. Zombie movies isn’t my thing, but people seem to love it.
Ben Whishaw in Cloud Atlas (2012)
This is a movie that features 6 individuals who belong to different generations and go on an emotional rollercoaster while seeing how their actions impact the lives of loved ones in an ever-changing world. And one of the multi-talented actors in the film (aside from Hugo Weaving that we saw earlier) is Ben Whishaw. His characters are in five settings and as five different people, one of them a woman.
Like the other actors and actresses in the movie, this is yet another amazing transformation that was demonstrated in such a minor role. Whishaw turned into the adulterous wife of Denholme Cavendish. And it’s true when you just glance at this female character; it takes more than a few seconds to realize that it’s a man!
Elle Fanning in 3 Generations (2015)
Elle Fanning was a 17-year-old high school senior when she played a teenager determined to change her gender to become a boy. Her character, Ray, is struggling to find acceptance from her mother (played by Naomi Watts), and grandmother (played by Susan Sarandon). The movie was supposed to be called About Ray. Fanning said it was “the most important character I’ve ever played and the most special to me.”
“When I was given the script, they were like, “this is like a family comedy/drama, but you’ll be a transgender boy,’ and I was like, ‘wait a second, like, whoa! Wow, OK!” I knew that it would be the biggest challenge that I’d ever have to do, but I think that it’s the most important role that I’ve ever done and the most special because there are a lot of teens out there that are like Ray, and I don’t think I’ve ever played a role that could relate to so many people and actually help people, at least even a tiny bit. You know, every little bit counts.”
RuPaul in The Brady Bunch Movie (1995)
It really comes as no surprise at all that the world’s top drag models can easily pull off the most convincing of women. His role in The Brady Bunch Movie may be brief, but he gave it his 100%. His role as a female guidance counselor was well done. And if you’ve never heard of RuPaul before seeing this movie, you would swear he was a woman.
The guidance counselor was tasked with helping Jan rebuild her self-confidence in the spoof film. Ru’s now-famous advice to channel your inner Charisma, Uniqueness, Nerve, and Talent (C.U.N.T.) wasn’t a part of the role, but if he was in that role today, his lines would surely be different. Have you seen his reality show? Yeah…
John Lithgow in The World According to Garp (1982)
The film was an adaptation of the John Irving novel, “The World According to Garp,” and it tells the story of T.S. Garp, an aspiring writer whose mother, Jenny (Glenn Close), maintains a shelter for abused women. One of the residents is a transgender woman who’s a retired football player by the name of Roberta Muldoon. She was obviously played by John Lithgow.
Her character was inspired to have the surgery after reading Jenny’s book, which became a radical feminist manifesto. The character of Roberta was considered one of the first sympathetic transgender characters in a commercially popular movie. John Lithgow is now 74, and his recent role as Winston Churchill in the incredible series, The Crown, is amazing!
Gwyneth Paltrow in Shakespeare in Love (1998)
I purposely put this one lower down on the list. Why? Because although Gwyneth Paltrow did win an Oscar for her role in this movie, it is by no means a convincing job as a male character. But she did juggle a number of nuances when she had to create her character. She played a woman who was pretending to be a man so she could play the part of Romeo in a 16th-century theater.
Even though her facial hair looks so poorly applied and she is just way too feminine to look like a man, she nevertheless did play the part of a man. And for that reason, she is on this list.
Fun fact: of the things Paltrow had to resort to for her role was “adjusting the center of her gravity” by placing a beanbag in her tights.