It's remarkable what actors and actresses go through in their careers to get a role and achieve their maximum potential. Some gain or lose weight, some excessively go to the gym to build up muscles. Others develop accents or change up their hair color or hairstyle. There are also actors and actresses who got to play characters of the opposite gender. Here are some examples of actors who had to perform in full-on drag for their movies, either for just one particular scene or even for the entire movie. Performances that later established or destroyed their careers in acting.
John Travolta - Hairspray
Edna Turnblad is the agoraphobic, plus-sized mother of Tracy, a plus-sized teenager trying to be a star. The first Hairspray movie was originally produced in 1988. What was peculiar about it was that the role of Edna was played by the famous drag queen of the time, Divine. When the movie was up for a remake in 2007, John Travolta, being already extremely successful when it came in musicals, was a prime choice for the producers. Even though the movie characters might need a better diet plan, the movie was a success. Travolta has continued his career in action movies, with his most recent one being 2019's Trading Paint.
Robin Williams - Mrs. Doubtfire
The late Robin Williams was one of the most loved actors of all time, who captured the audience’s hearts with every movie—sometimes even terrified them! In the 1993 movie, Mrs. Doubtfire, Williams played the role of Daniel Hillard, an actor who had just gone through an awful divorce, who ended up dressing as a female housekeeper for his ex-wife just to spend time with his children. The movie not only managed to get everyone’s attention with its plot, but it also caught the attention of the Academy as it won that year’s Oscar for makeup. There was some talk about a sequel in the 2000s, but it was canceled due to script problems.
Nathan Lane - The Birdcage
The movie The Birdcage was a remake of the French-Italian film called La Cage aux Folles. It follows the story of a gay cabaret owner and his partner who agree to pretend to be a straight couple to meet their son’s fiancée’s conservative Republican rich parents. Nathan Lane played the role of Albert Goldman, the flamboyant partner of Armand Goldman, played by Robin Williams. Armand, being so clearly not your everyday guy, disguises as his son’s mother. Nathan Lane has since gotten married to his partner Devlin Eliott in 2015.
Jack Lemmon - Some Like It Hot
Jerry (Jack Lemmon), a jazz double bass player, and his friend and bandmate Joe (Tony Curtis), a saxophone player, witness a gangster crime and decide to flee the state. To do that, they disguise themselves as Daphne and Josephine and join an all-female band with Sugar Kane (Marilyn Monroe) as their lead singer. This was the plot of one of the greatest films of all time, Some Like It Hot, which was released in 1959. The movie was a great success and received almost perfect reviews and quite a lot of award nominations. It was, however, rumored to have been condemned by the Roman Catholic Church for being morally objectionable.
Dustin Hoffman - Tootsie
In the movie Tootsie, Dustin Hoffman plays the role of Michael Dorsey, an unsuccessful and difficult actor who ends up disguising himself as Dorothy Michaels in order to get a role on a trashy hospital-themed soap opera. To prepare for this role, Dustin had to watch the previously mentioned La Cage Aux Folles several times along with visiting the sets of already existing soap operas and making extensive research and makeup tests. He was, however, shocked that even though he managed to pass as a woman, he would never pass as a beautiful one.
Julie Andrews - Victor Victoria
Victor Victoria is a story about a woman named Victoria, who pretends to be a man named Victor. Oddly enough, Victor impersonates women for a living. The movie was released in 1982 and was a remake of the German film Viktor und Viktoria. Julie Andrews managed to grab the audience’s attention with her wonderful performance in the movie. The movie itself got nominated for many Academy Awards and even managed to win the Award for Best Original Song Score. It was written and directed by Blake Edwards; the person responsible for the Pink Panther films.
Patrick Swayze - To Wong Foo, Thanks For Everything! Julie Newmar
Patrick Swayze, John Leguizamo, and Wesley Snipes put on their wigs in 1995 and starred in the movie To Wong Foo, Thanks For Everything! Julie Newmar as the drag queens Vida Boheme, Chi-Chi Rodriguez, and Noxeema Jackson. It is a movie about three queens who go on a road trip. The movie was shot in New York and featured many of NYC’s famous drag queens at that time like Emmy award winner RuPaul, celebrity transgender woman Candis Cayne, and famous drag queen Lady Bunny, among many others. Overall, the film received good reviews and is fondly remembered within the LGBT community.
David Spade – Jack and Jill
David Spade dressed in drag for his role in the comedy movie Jack and Jill and, although he looked hilarious and gave a great performance, the movie was not well received by the critics and it wasn’t a huge success. David began his career on Saturday Night Live. He has stuck mainly to the comedy genre throughout his time in front of the camera. Two of his long-running TV shows were Just Shoot Me! and Rules of Engagement. David performed at the Moontower comedy festival in Austin, Texas in April 2019.
Hugo Weaving – The Adventure of Priscilla, Queen of the Desert
Hugo Weaving participated in one of the movies that helped pioneer the entrance of more alternative subjects into the mainstream film industry. He starred in the full movie The Adventures of Priscilla, Queen of the Desert, together with Guy Pierce, with their characters going on a journey throughout the Australian outback. The film was a success and Hugo has had a successful career, even participating in the Marvel movie franchise as Red Skull, one of the enemies of Captain America. He will participate in 2019 in a theater production with his son, Harry Greenwood on the play, Cat on a Hot Tin Roof.
Amanda Bynes – She’s the Man
Amanda Bynes dressed as a guy in the movie She’s the Man, where her character was so determined to get into a good soccer team, that she was willing to pretend that she was a boy. Amanda Bynes was everyone’s favorite teenage actress. However, as it tends to happen with young stars, she has had some troubling issues that have included legal problems. As of April 2019, she’s been in a drug rehab center for about three months and her family has told the press that she’s doing well and working on her recovery.
Wesley Snipes - To Wong Foo, Thanks for Everything! Julie Newmar
The plot of this film is actually a bit reminiscent of the Hugo Weaving movie. In this case, Wesley Snipes' character was with two other friends, going on a road trip. The difference was that in this case, the journey would take place in the United States. Wesley showed his immense versatility, considering that later on, he would play Marvel vampire Blade on Blade Trinity. It has been confirmed in 2019 that Snipes will appear in the thriller Payline where he will assume the part of the villain. Snipes has had some major financial issues with the IRS recently, despite having a fortune estimated at $10 million.
Barbra Streisand - Yentl
Barbra Streisand is a legendary actress, singer, and activist who has never been afraid of trying new things. She showed this when she appeared on Yentl, a movie where she starred in and which she also produced, directed, and co-wrote. Here, Barbra took the place of her brother after her father died. Barbra has since built an impressive legacy and she has even given some advice to Lady Gaga. Gaga played the same role Streisand did so many years ago on A Star is Born. Streisand's co-star from said movie, Kris Kristofferson, will perform with her in July 2019 at the British Summertime Hyde Park.
Jeffrey Tambor - Transparent
Jeffrey Tambor has had a long career in Hollywood, with usually supporting but hilarious roles such as the one in the TV show, Arrested Development. However, he definitely made headlines when he accepted a TV role on Transparent, playing the part of a transgender woman. It was recently announced that his character will be killed in the final season of the show after Tambor was involved in a scandal in which some series accusations were made against him. There has been no arrest but the network has decided that letting Tambor go would be the best decision.
Eddie Redmayne – The Danish Girl
Eddie Redmayne had the challenging task of portraying Lili Elbe, the first transgender woman who went under a doctor’s knife in order to fully transition to a female. Redmayne’s portrayal was so moving and realistic that it earned him an Academy Award nomination. This was after having won the award the prior year for his portrayal of Stephen Hawkins on the Theory of Everything. Eddie has shown his versatility by opting for a totally different role as Newt Scamander in the Fantastic Beasts and Where to Find Them saga which stems from the Harry Potter universe.
Jonathan Brandis - Ladybugs
Jonathan Brandis’ character on Ladybugs would do anything for a friend, even dressing as a girl and donning a blonde wig to help a girls' team win a competition. Another iconic role of Brandis was in the TV show It, inspired by Stephen Kings’s work, where Brandis played the main character. However, Jonathan’s career didn’t take off as he might have expected and what followed was a series of minor roles, which led him into a vicious cycle that ended in 2003, when he killed himself in his apartment building in Los Angeles.
Alexander Skarsgård - The Diary of a Teenage Girl premiere
Alexander Skarsgård made celebrity news when he decided to dress up in a very different way for the red carpet of the premiere of his film, The Diary of a Teenage Girl. Alexander reached international fame for his role in the HBO hit TV show True Blood, where he played the part of vampire Eric Northman. He won numerous awards in 2017 for his impressive role on Big Little Lies, including a Golden Globe Award. His latest project was titled The Kill Team and it was released worldwide in April of 2019.
Corey Haim – Just One of the Girls
Corey Haim played a character who tried something really different in order to deal with the high school bullies that tormented him. He decided to dress as a girl to enter the school as a way to avoid the bullies, but complications soon ensued. Corey, who was a teen idol and rose to fame quickly, had several problems with substances and led a chaotic life that ended with his death in 2010. He died of pneumonia after developing pulmonary edema. However, he will always be remembered by many as a teenage heartthrob.
Woody Harrelson – Anger Management
You might blink and you’ll miss it, but Woody Harrelson had a funny cameo role in Jack Nicholson’s Anger Management, where he appeared in drag. Woody has participated in everything from comedies to action movies and detective thrillers, getting hefty paychecks for his performances. The younger generations might remember him for his role as Katniss’ mentor on The Hunger Games but one of his most recent movies was Zombieland, which was an unexpected success. He’s currently shooting the sequel together with co-stars Emma Stone and Jesse Eisenberg. He appeared in the Netflix movie The Highwayman in 2019.
Arnold Schwarzenegger – Junior
Arnold Schwarzenegger has certainly done it all, from participating in male beauty pageants to becoming a Hollywood superstar. His versatility is unparalleled! He played an iconic role in the Terminator franchise, which was an action film as well as True Lies, where his co-star was Jamie Lee Curtis. But he also portrayed hilarious characters, like the one on Junior, where his role was that of a man who was with child, of all things! In April 2019, Arnold celebrated his son’s graduation from the collegiate level and he publicly congratulated him for his achievement and obtaining a Business degree.
Hugh Laurie – A Bit of Fry and Laurie
Hugh Laurie might be better known for his excellent role in the long-running medical drama House, where he played the role of Dr. Gregory House, a practicing physician who was addicted to prescription drugs. However, Hugh has had ample background in comedy, like when he participated in the BBC show A Bit of Fry and Laurie where he co-starred with fellow actor Stephen Fry. The show was a success and both Laurie and Fry appeared in drag for numerous sketches. It's been confirmed in April 2019 that Laurie has an upcoming HBO series called Avenue 5.
Angelina Jolie - Salt
Angelina Jolie has never been afraid of taking risks and going to extremes in order to best represent her characters. One such occasion was the movie Salt, where her character disguised herself as a male naval officer. The costume was so believable that her son Maddox didn’t recognize her when he went to visit her on the set and her then-partner Brad Pitt even refused to kiss her. Angelina and Brad have finalized their divorce in 2019 but they share the custody of their children. Jolie will participate in the new project Those Who Wish Me Dead and in April 2019, it's been revealed that Nicholas Hoult will be her co-star.
RuPaul – RuPaul’s Drag Race
He’s one of the main responsible figures for bringing drag into the mainstream pop culture. With his reality TV show RuPaul’s Drag Race, RuPaul appears both in his male persona as well as in his female persona and is the host and one of the judges of the show. He has released singles and music videos and has become a sort of mentor and inspiration for many in the drag community. Usually seen with blonde hair when in drag, he has never been afraid of changing his style. RuPaul is currently hosting the 11th season of his successful reality TV show competition.
Sean Bean - Accused
Although the entire world knows him for his role as one of the most honorable men in Westeros in the hit HBO series Game of Thrones, Sean Bean has been known for taking risky and challenging roles. An example of this was the character he played in the TV show Accused, which was a BBC drama that played out mainly in legal court. His portrayal earned him an International Emmy Award and plenty of critical acclaims. Bean currently has two new projects he’s focused on, Curfew and World on Fire.
Terence Stamp – The Adventures of Priscilla, Queen of the Desert
This legendary actor has had a long-spanning career. One memorable interpretation was as one of the drag queens in the epic trip portrayed on The Adventures of Priscilla, Queen of the Desert, together with Hugo Weaving and Guy Pierce. We do have to say that Stamp doesn’t look bad in women’s clothes. He might have been known for toughest roles like that of General Zod in the Superman movies, but he has undoubtedly shown his immense versatility on various occasions. Terence is set to appear in the new Netflix movie Murder Mystery, together with Jennifer Aniston and Adam Sandler.
John Leguizamo – To Wong Foo, Thanks for Everything! Julie Newmar
John Leguizamo is an outrageous comedian and he showed some of his skills in the movie To Wong Foo, Thanks for Everything! Julie Newmar. Here, he played the part of a New York City drag queen who embarked on a road trip with some of her friends. Leguizamo has been involved in comedy for a long time now, and he has had a long career both as an actor, playwright, and a stand-up comedian. He became the face of Pepsi’s new ad campaign in April 2019. Meanwhile, his latest stand-up special is currently streaming on Netflix.
Michael C. Hall - Hedwig and the Angry Inch
You might know him as a cold-blooded serial killer doctor from the show Dexter, but Michael C. Hall went on Broadway to play a role far from his prior ones. On stage, he became Hedwig, in the show titled Hedwig and the Angry Inch. He got great reviews for his performance in the long-established musical after being away from the musical arena since his performance on Cabaret. Michael will be starring in a new series by Mans Marlind called Shadowplay, alongside Taylor Kitsch. The two-part series will run for sixteen episodes.
Miguel A. Núñez, Jr. – Juwanna Mann
In another story about loving sports so much you would dress as part of the opposite gender, Miguel A. Nuñez Jr. played Juwanna Mann, the female version of his character, Jamal. After being kicked out of the male professional league for his outrageous antics and going into bankruptcy, Jamal infiltrated the women’s league in this romantic comedy. The movie was received with mixed reviews and this was one of the few starring roles Nuñez Jr. has had in his career. He currently stars in the TV show The Family Business and has some upcoming roles on A Perfect Date and Only You & Me.
Rupert Everett – St. Trinian’s
This movie was actually an independent reboot following five prior movies made based on the work of cartoonist Ronald Searle. Rupert Everett played the role of the headmistress of a high school filled with problematic girls. Everett’s portrayal was hilarious but the film was received with ambivalent reviews. Everett has had a prolific career, starring with legendary actress Julia Roberts on My Best Friend’s Wedding in 1997. One of his current projects is in theaters. The Happy Prince has Everett playing the role of Irish playwright and poet Oscar Wilde, portraying him during his last years.
Cillian Murphy – Breakfast on Pluto
Cillian Murphy had been performing on the theater stage and had participated in different movie roles by the time he did Breakfast on Pluto, which earned him a Golden Globe Awards nomination. He became even more popular after his role as a villain on Batman, where his personification was both exciting and terrifying as he played with the mental health of his victims. Since then, Murphy has continued to have a career in both films and theater. He has been portraying Thomas Shelby on Peaky Blinders since 2013. In April 2019, critics have also raved about his performance in the play Grief is the Thing with Feathers.
Lee Pace - Soldier's Girl
Lee Pace played Calpernia Adams, the love interest of Barry Winchell, a soldier who fell in love with her, a transgender woman performer. The full movie was based on a true story and the romantic film evolved into a drama, in which Barry ended up being killed by a fellow soldier. Pace’s performance was flawless. Fortunately for him, he has continued to take risks during his career. An example of this was his appearance in the play Nassim, where the actors received the script only during the play, making it a groundbreaking feat that was greatly praised by the critics.
Jamie Foxx – In Living Color
In Living Color represented defiance to the norm. It was a comedy sketch TV show that aired on Fox in four seasons and where actors like Jamie Foxx started to become known. Foxx, a successful actor, and singer and Academy Award winner started here alongside stars like Jim Carrey and Jennifer Lopez. Jamie appeared in drag portraying the character Wanda and her funny antics. Foxx recently posted a picture with former boxer Mike Tyson hinting at the possibility of a possible biopic. Well, he might need to spend plenty of hours at the gym to prepare for that. Reportedly, Jamie has been looking forward to this role for years now.
Chris Pine – Surrender, Dorothy
Chris Pine might be known for roles in romantic comedies like Just My Luck and This Means War, or maybe you saw him in the Star Trek film released in 2009. However, way before all of this, Pine appeared alongside Diane Keaton in the movie Surrender, Dorothy, where he played a gay young man who sometimes liked to dress in drag. Thanks to his character’s fashion sense, we have to say that Chris looks great as a woman! He will be appearing in the 2020 release of Wonder Woman 1984 after doing Wonder Woman in 2017.
Ving Rhames – Holiday Heart
In Holiday Heart, Ving Rhames went a bit out of his usual tough guy roles in order to portray a gay man who performed as a drag queen in a nightclub. However, he ended up becoming a father/mother figure to Niki, a girl with a mother addicted to drugs who he managed to raise while facing challenging odds and obstacles. The television movie received critical acclaim and several nominations, including a Golden Globe. Rhames is still participating in several acting projects. His latest appearance was in 2018's Mission: Impossible- Fallout where he once again reprised his role of Luther Stickell.
Matt Leblanc - All the Queen’s Men
In 2001, Matt Leblanc put on his best wig and went on to shoot the movie All the Queen’s Men. It’s a film about a team of British special services agents who disguised themselves as women to infiltrate an all-female Enigma factory in Berlin in order to retrieve a decoding device that could help them win the war. Matt played the role of Captain Steven O’Rourke. Since he was still actively filming for his hit TV show Friends at that time, Matt had to fly back and forth once a week in order to be there for both the movie’s and the show’s shootings.
Martin Lawrence - Big Momma’s House
In order to protect a woman and her son and arrest the perpetrator of an armed robbery, FBI Agent Malcolm Turner disguises himself as their big, over-the-top grandma. The movie Big Momma’s House was such a hit that they made two follow-up sequels. However, it didn’t all go without any problems. Martin, in his attempt to prepare for the film, went out jogging wearing sweaters in 100 degrees weather, which resulted to him falling into a three-day coma due to the heat. His fat suit even had built-in cooling tubes to prevent Martin from overheating again.
Kurt Russell - Tango & Cash
Tango, played by Sylvester Stallone, and Cash, played by Kurt Russell, are two LAPD crime-fighting officers who try to set the score with their arch-nemesis after being framed and put to jail. That’s what the movie Tango & Cash was all about. In a scene where Cash is in a night club and surrounded by police, he finds Tango’s sister who helps him escape by putting on a perfect smile and dressing him up as a woman. While the movie was being shot, it faced many production problems with people coming and going. However, it managed to get released in 1989 and became a hit.
Tony Curtis - Some Like It Hot
Even though Tony Curtis’ character gets the girl in the movie, Tony and Jack Lemmon had to test if their smiles were good enough and whether or not they would get noticed walking around in their disguises. So, when they first got dressed to impress, they walked around Goldwyn Studios to see if anyone would recognize them. The ultimate test was when they entered the ladies bathroom to fix their makeup and none of the ladies there complained or said anything. This exact scene was later recreated and added to the movie when the characters were fleeing on a train.
Eddie Murphy - The Nutty Professor
The Nutty Professor is a movie starring Eddie Murphy, Eddie Murphy, and, of course, Eddie Murphy. He showed an immense amount of talent playing the role of Professor Sheran Klump, an obese and soft-hearted professor, who takes a special kind of chemical to turn into Buddy Love, his slim but obnoxious alter ego. In this movie, Eddie also plays the roles of his character's parents Papa Cletus Klump and Mama Anna Klump, his grandmother Granny Ida Mae Jenson, and his brother Erni Klump. The movie was such a commercial success that they even made a sequel in 2000, Nutty Professor II: The Klumps.
Willem Dafoe - The Boondock Saints
Willem Dafoe in The Boondock Saints plays the role of FBI Agent Smecker. Smecker is hunting down the Irish Catholic brothers, Connor and Murphy, who became vigilantes trying to wipe out Boston’s criminal world in the name of God. Smecker tried saving the day by showing up in an operation dressed as a woman. The movie was initially said to have one of the best scripts in Hollywood but ended up having some production troubles, especially after being associated with the 1999 Columbine High School massacre. They managed to get a sequel out, The Boondock Saints II: All Saints Day, that was released in 2009.
Johnny Depp - Ed Wood
Edward Wood was an American low-budget science fiction director who just so happened to have a female alter ego called Shirley. The movie Ed Wood directed by Tim Burton and starring Johnny Depp is a biographical comedic drama that tells us his story. Depp later said that to play this character he had to have a mixture of blind optimism and the Tin Man’s enthusiasm. A pretty comedic fact about this movie is that it cost more money to make than the total money Edward Wood needed for all his movies combined.
Michael J. Fox - Back To The Future Part II
After having visited the year 2015 in the first movie of the Back to the Future trilogy, Marty McFly now has to go back to the year 1955 again to prevent having disastrous changes in 1985. Without, of course, interfering with his first trip. Michael J. Fox showed us great versatility by not only playing the main character Marty but also his son Marty Jr. and his daughter Marlene. The two parts were filmed back to back. The biggest challenge wasn’t to get Michael to dress as a woman for the camera but to imagine the year 2015. That’s how they came up with the concept of hoverboards, to begin with.
Ryan Gosling - All Good Things
Inspired by the life of Robert Alan Durst, a person who was accused of killing his wife, the movie All Good Things got released in 2010. Mr. David Marks, the protagonist played by Ryan Gosling, was suspected but never went on trial for his wife’s murder. It is said that the accused murderer disguised himself as a woman to hide, as was shown in the film. There is a scene in the movie where the couple is arguing and David pulls Katie’s hair. Ryan admitted that he felt so bad for doing that, he even sent Kirsten Dunst, who played the role of Katie, a bouquet of flowers the next day!
Tyler Perry - Diary of a Mad Black Woman
Tyler Perry created his character Mabel Madea Simmons for the movie Diary of a Mad Black Woman. It was inspired by the women in his life, his mother, his aunts, and of course his sisters. The story is about a couple who is seemingly doing okay until the wife discovers that her husband wants a divorce. In this movie, Tyler also plays the roles of uncle Joe Simmons and Brian Simmons. The movie was such a success in 2005 that they moved on to make a sequel called Madea’s Family Reunion, which was released one year later.
Cate Blanchett - I'm Not There
To embody all of Bob Dylan’s public personas, Tod Hynes, the director of I’m Not There, had six different Hollywood actors to portray him in different stories to create one full movie. As the only woman among the six, Cate Blanchett played the role of Jude Quinn, a famous former folk music singer who received hatred and accusations from his fans after performing with a full band and electric guitars. With her role, Cate got several award nominations including an Academy Award nomination for Best Supporting Actress. She managed to win a Golden Globe for the same category. The film was so good, even Bob Dylan himself liked it!
Tom Hanks - Bosom Buddies
Two young men, Kip and Henry, decide to disguise themselves as women so that they can live in an apartment they can actually afford. The '80s sitcom Bosom Buddies starring Tom Hanks in the role of Henry aka Buffy aired for a total of 37 episodes; making two successful seasons. Leaving Tom Hank’s dated hair aside, one could say he actually looked good! Tom even met his now-wife Rita Wilson while she was a guest star in an episode of the series in 1981. They were both in relationships at that time, but they later got married in 1988.
Stephen Dorff - I Shot Andy Warhol
Yet another example of male actors who look incredibly good in and out of drag! Stephen Dorff played the role of Candy Darling, a transgender woman who was an icon during her time, in the 1996 movie I Shot Andy Warhol. The character also starred in many of Andy Warhol’s films. The movie tells us about the life of the radical feminist Valerie Solanas and how she ended up shooting Andy Warhol. Stephen said he felt ready to play this role as he had his pretty makeup, was waxed, and had heels on!
Shawn & Marlon Wayans - White Chicks
In the movie White Chicks, brothers Shawn and Marlon Wayans played the roles of two FBI agents, Kevin and Marcus Anthony Copeland, who had to put on a dress and go undercover as white women in order to solve a pair of kidnappings. You have to admit that there is a comedic sense to it in a way. However, the film did receive tons of bad reviews for its controversial plot. Many said that it was offensive and predictable. The audience did seem to have enjoyed it, though. Marlon confirmed in 2018 that they will be working on a sequel. Let’s see what they come up with this time.
Miguel Bose - High Heels
Pedro Almodóvar’s films are always hard to explain. In one of his movies, the 1991 melodrama High Heels, Spanish pop new wave singer Miguel Bose played the role of Judge Edwardo Dominguez aka Letal, the drag queen. The movie is about a mother who returns home after 15 years to find her daughter married to one of her ex-boyfriends. She then tries to repair their broken mother-daughter relationship. Miguel’s role was surprisingly difficult to cast, as the actor would have to be convincing as a judge and as a drag queen.
Jude Law - Rage
You can just go ahead and add Jude Law to your list of men who look awesome in drag! The movie Rage, which was released in 2009, is about a young blogger in New York who shoots behind-the-scenes interviews on his cell phone. In this film, Jude plays the role of Minx. One would say he is so convincing and good at it that it’s actually hard to recognize it’s him! The film can definitely be described as experimental. After all, it was the first movie to ever debut on mobile phones.
James Franco - Candy Magazine
We are not exactly talking about a movie here. Candy is the first fashion magazine to celebrate cross-dressing and androgyny in all their forms. James Franco has always been a bit provocative and freaky. In 2010, he was on the cover of Candy magazine in full drag! The pictures were taken by the famous photographer Terry Richardson. The magazine has since collaborated with artists like Lady Gaga, Marilyn Manson, and Miley Cyrus. All the photoshoots have been extremely memorable and included unclothed photos or just photos of gay or transgender celebrities.
Barry Watson - Sorority Boys
The 2002 film Sorority Boys follows the story of three frat boys who get kicked out of their dorm. They then decide to have a makeover and pose as girls just so that they can go live in the "DOG" house with all the other girls who are deemed unattractive. You have to admit that it sounds White Chicks bad, and the truth is it was. The film went on to receive immensely bad reviews for being sloppy and insulting. As a result, it barely broke even and only grossed a total of $12.5 million against a $12 million budget.
Adam Sandler - Jack and Jill
In the movie Jack and Jill, Adam Sandler played twin siblings. Jack is an ad executive and family guy who's trying to survive Thanksgiving with his annoying sister Jill who came to visit. The movie was so bad that it was the first movie in the Golden Raspberry Awards history to win every category. That includes the worst picture, worst actor, worst actress, worst director, and many more. But hey, a paycheck is a paycheck, and Adam sure got one for starring in it—one worth $20 million, to be exact.
Jared Leto - Dallas Buyers Club
Dallas Buyers Club is a really tear-dropping movie. It follows the story of Ron Woodroof, played by Matthew McConaughey, who, after being diagnosed with AIDS, tries to help other patients get their medication. Jared plays the role of Rayon, a transgender woman who also has the disease and helps Ron with his cause. Jared had to lose 30 pounds, wax his entire body, and shave his eyebrows to play the role. He also stayed in character the entire time the movie was being filmed. His dedication and hard work granted him an Oscar for Best Supporting Actor.
Tim Curry - The Rocky Horror Picture Show
Newly engaged couple Janet and Brad’s car breaks down near a castle. As a last resort, they enter the property of Dr. Frank-N-Furter looking for a phone to use. The 1975 musical film Rocky Horror Picture Show was by all means ground-breaking. Tim Curry played the role of the transgender scientist from the planet Transylvania. The film was deemed of such importance that, in 2005, it was chosen to be preserved in the United States’ National Film Registry for being historically, aesthetically, and culturally significant. As Curry’s song says: don’t dream it, be it!
Billy Crudup - Stage Beauty
Loosely inspired by true events and based on actual personalities, Stage Beauty is a story about the first female actor in British theatre and how she managed to go from a theatre dresser to getting the role of Desdemona in Othello; replacing the male actor she once worked for. The two lead actors, Billy Crudup and Claire Danes, actually fell in love in real life. Billy left his then-pregnant long-time girlfriend to be with Claire and they later became a couple. All in all, the film is a very nice and romantic period drama.
Neil Patrick Harris - Hedwig and the Angry Inch
Hedwig and the Angry Inch is a fan-favorite musical production that has been recreated time and time again. After being in front of the camera for nine seasons of the hit show How I Met Your Mother, Neil Patrick Harris immediately took his prowess to the stage and played Hedwig for the first Broadway production of the musical. It managed to win several Tony Awards including the one for Best Revival of a Musical and of course Best Lead Actor, which went to Harris with his legen...wait for it...dary performance! It is a story about a transgender punk rock girl traveling around the U.S. with her band while telling the story of her life.
Liev Schreiber - Taking Woodstock
Taking Woodstock is a movie about Woodstock, clearly! It tells the story of the man who set in motion the generation-changing concert in the summer of 1969. Liev Schreiber played the role of transgender woman Vetty Von Vilma. Surprisingly, it was not the first time Live had to put on a dress in his career. He previously did drag in his movie Mixed Nuts back in 1994. The movie premiered in the 2009 Cannes Film Festival and received good reviews. It was based on the memoir Taking Woodstock: A True Story of a Riot, a Concert, and a Life.
David Duchovny - Twin Peaks
Twin Peaks was a TV show that aired between 1990 and 1991. It tells the story of an FBI agent trying to investigate a murder in the town of Twin Peaks. The X-Files' David Duchovny came in to play Denise Bryson, a former Drug Enforcement Administration Special Agent. It was probably refreshing for Duchovny to go from full-time alien hunter to skirt-and-heels-wearing FBI agent—especially for the people watching at that time! David stayed in Twin Peaks for three episodes during the second season of the show. He liked it so much that he came back in the third season in 2017!
Freddie Mercury - I Want To Break Free
We have all heard or seen Queen lead singer Freddie Mercury’s story. He is one of the biggest rock stars and music icons who has ever existed before and after his tragic death related to HIV. Queen’s eleventh album, The Works, featured the song I Want To Break Free, which is now considered to be an anthem in all fights against oppression. In its music video, all the band members are dressed in female clothing in an attempt to create a parody of the long-running soap opera called Coronation Street. Even though the music video was praised in the UK, it was considered highly controversial in the United States.