Drag in Hollywood: The Fiercest Film Moments from Julie Andrews to Tyler Perry

By Edene SoffrinLast Updated Jun 25, 2020 7:43:45 PM ET
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Photo Courtesy: Michael White Productions/IMDb

Listen here, Hunty. RuPaul's Drag Race is undeniably one of the highest rated reality TV shows in the world — for darn good reason. The tongue-in-cheek competition series has raised the art form to a glittered and gorgeous global platform, and viewers just can’t get enough of it.

However, RuPaul may have brought dressing in drag to the forefront of our consciousness, but the practice isn’t new, even in Hollywood. Countless stars have dressed in drag in various movies and TV shows, some long before the show’s debut. From Tyler Perry to the legendary Julie Andrews, many celebs have slipped into new gender roles to help folks understand that it’s okay to express yourself in any number of ways.

Tyler Perry

Tyler Perry is known for playing tough, gun-toting Mabel "Madea" Simmons in many of his stage plays and movies. Perry has often lamented that the Madea costume and wigs are too hot, but the character is so popular that he has kept her around for decades — and fans love him for it.

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Photo Courtesy: WatchMojo.com/YouTube

The writer and director officially retired the character with his stage play, Madea's Farewell, which finished touring in February 2020. "She's also run out of things to say. Maybe one day she'll return, but for right now, no, I think I'm done," he shared in an interview with CNN. It’s hard to imagine that any comical drag character could ever be missed more.

Angelina Jolie

In her 2010 film Salt, Angelina Jolie implemented a series of disguises as she attempted to clear her name after being accused of espionage. One of the most amazing options included dressing up as a male naval officer.

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Jolie's son, Maddox, visited the set while she was in this particular disguise, and he didn't even recognize her. "'He hung out with me for a while, and when he realized it was me, he was just freaking out," the actress told The Daily Mail. She also admitted that her look was so believable that her then-husband, Brad Pitt, wouldn't even kiss her while she was in costume.

Tim Curry

Tim Curry rose to prominence with his iconic transvestite character Dr. Frank-N-Furter from The Rocky Horror Picture Show. The actor took to the stage with confidence in full makeup, thigh-high stockings and heels, launching one of the most enduring cult movie classics of all time. He reprised the role when the play became a feature film.

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When the original play first premiered, Curry admitted to the Los Angeles Times that he had some reservations about playing the part at first. However, he ultimately shrugged those fears aside and was forever grateful that he did. "I just thought it was such a good part, people would know you were acting," the actor shared.

Eddie Redmayne

The 2015 film The Danish Girl told a loose adaptation of the life of artist Lili Elbe, one of the first known recipients of gender reassignment surgery. Eddie Redmayne stepped up for the role and was nominated for the Academy Award for Best Actor for his work.

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In preparation for the role, Redmayne studied issues facing the transgender community, including prejudice and violence. He revealed that he felt very self-conscious on set at times. "You walk in, and the crew is looking at you," he told Variety. "The feeling of being gazed at and scrutinized, and the fear is there."

Cate Blanchett

Cate Blanchett was one of six stars in the 2007 flick I'm Not There, inspired by the life and music of the legendary Bob Dylan. Blanchett acted alongside Christian Bale, Marcus Carl Franklin, Richard Gere, Heath Ledger and Ben Whishaw, with each one of them playing a different public persona of Dylan's at different stages of his life.

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Blanchett's persona, Jude Quinn, represented Dylan's expansion of his music as he began to experiment with rock sounds. His new tastes drew criticism from those in love with his folk music. The role required the actress to dress up as Dylan, covering up her famous blonde locks.

Ving Rhames

The 2000 television film Holiday Heart showed actor Ving Rhames in a completely different light than what you see in the majority of his films. His deep voice and muscular body have earned him "tough guy" roles since he started acting, so this movie role was a big step out of his comfort zone.

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In this film, Rhames played a gay drag queen who takes in a drug addict and her daughter in an attempt to save them from the dangerous, crime-filled streets of the city. The film also starred Alfre Woodard, who received a Golden Globe nomination for her role. Unfortunately, the Globes snubbed Rhames, who did not receive a nomination for his work.

Nathan Lane

Nathan Lane starred as the flamboyant Albert Goldman, the life partner of drag nightclub owner Armand Goldman (played by Robin Williams). In the film, their two characters try to hide their relationship for the sake of Armand's biological son, who is meeting the ultraconservative parents of his girlfriend.

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Lane's hilarious dramatics shined in the movie, and he was also praised for showcasing the issues that the LGBTQ community faces daily in terms of public perception. The film was nominated for a number of awards, including Outstanding Performance by a Cast in a Motion Picture at the 1997 Screen Actors Guild Awards.

Glenn Close

The 2011 drama Albert Nobbs featured actress Glenn Close as the titular character, a butler at a hotel in late 19th-century Dublin. The role transformed Close into a character who was born a female but had spent 30 years living as a man.

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Close first played the character in a 1982 stage production and tried for almost three decades to have it made into a film. Although the movie received mixed reviews from critics, Close was nominated for an Academy Award for Best Actress at the 84th Academy Awards in 2012 for the role.

Robin Williams

When you stack up all of Robin Williams’ numerous roles over the span of his career, one of the most memorable and most beloved is in the hilarious flick Mrs. Doubtfire. In the film, Williams dresses up as an elderly British nanny to spend extra time with his three kids while he’s in the middle of a messy divorce.

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Before his tragic death in 2014, Williams revealed on a Reddit discussion board that he used to walk through San Francisco in character and even visited a sex shop on one occasion. The film, which co-starred Sally Field and Pierce Brosnan, ultimately became the second highest grossing film of 1993 worldwide.

Martin Lawrence

Martin Lawrence stepped into drag with some attitude for his 2000 comedy Big Momma's House. He starred as an FBI agent who goes undercover as an elderly African American grandma in order to get more intel to capture an escaped criminal. Although the film wasn't well received by critics, audiences loved it, which led to the production of two sequels.

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Even more interesting, Lawrence's role as Big Momma wasn't his first time acting in drag. He had previously dressed up as a woman to play the iconic character Sheneneh Jenkins on his sitcom Martin in the 1990s.

Tom Hanks and Peter Scolari

In the 1980s sitcom Bosom Buddies, Tom Hanks and Peter Scolari starred as two single men struggling in the creative advertising field. The men lose their apartment to a demolition order, and the only place they can afford is in a female-only complex. To get away with living there, the two dress up in drag and try their best to trick residents into believing they are women.

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The series was conceived by TV production company Miller and Boyett as a male counterpart to the hit sitcom Laverne & Shirley. Unfortunately, the show only lasted for two seasons, but it was a memorable buddy comedy with an interesting twist that launched the careers of Hanks and Scolari.

Hilary Swank

The 1999 biographical film Boys Don't Cry told the true story of Brandon Teena, a transgender man who was tragically murdered in a hate crime in the early 1990s. The murders of Teena and Matthew Shepard, a gay college student, led to increased lobbying for hate crime laws in the United States.

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Hilary Swank took on the difficult role in the film and earned both the Academy Award and Golden Globe Award for Best Actress in 1994. In 2019, the film was selected for preservation in the United States National Film Registry by the Library of Congress.

Shawn Wayans and Marlon Wayans

Brothers Shawn and Marlon Wayans are known for their comedic acting careers and have played some wild characters in the past. However, their roles in the 2004 comedy White Chicks may just take the cake on wacky. The two played undercover FBI agents who dress up like white women in order to solve a kidnapping plot.

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Marlon has admitted that he wants a sequel to the film, but nothing has been confirmed yet. "That’s a movie that will make half a billion dollars or more — no joke — because that’s how badly people want it," the comedian shared with Buzzfeed News.

Patrick Swayze, Wesley Snipes and John Leguizamo

The 1995 comedy To Wong Foo, Thanks for Everything! Julie Newmar showcased Patrick Swayze, Wesley Snipes and John Leguizamo in a completely new light as the world had never seen them before — and never could have imagined, at least for the ultra-masculine personas of Swayze and Snipes. The trio set the big screen on fire as three New York City drag queens.

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Although they were all excited to play their individual roles, they quickly grew tired of all the makeup and costuming involved in becoming these characters. "Wesley absolutely hated it. When we wrapped Wong Foo, he held a ceremonial funeral for his gender bender wig and clothes," Swayze wrote in his memoir, The Time of My Life.

Neil Patrick Harris

Neil Patrick Harris proudly performed in drag for the 2014 Broadway Production of Hedwig and the Angry Inch. He even went on to earn a Tony Award for his performance in the titular role.

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Photo Courtesy: Theo Wargo/Getty Images for Tony Awards Productions

The play centers around the story of fictional rock and roll band the Angry Inch, led by transgender singer Hedwig. It was a tough role for Harris to take on, but he was dedicated to the process. "In a role like this, you have to commit. You can't tiptoe, you have to bulldoze," he shared with The Hollywood Reporter.

Amanda Bynes

Confusion and comedy ensued in the 2006 flick She's the Man, which served as a modern retelling of William Shakespeare's play Twelfth Night. The movie starred Amanda Bynes as Viola, who pretends to be a boy in order to play soccer after her own team is disbanded.

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Although the movie was purely meant to be funny, it had some real repercussions for Bynes, who struggled with seeing herself as the character after filming wrapped. "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 told Paper magazine. "[It was] a super strange and out-of-body experience."

Matt LeBlanc

Matt LeBlanc will always be known for his famous role as Joey on Friends. However, he stepped out of his comfort zone to perform in drag for a film as well. In the 2001 film All the Queen's Men, the actor played an undercover soldier in the British army who dresses up as a woman to retrieve an Enigma machine from Germany.

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Once he was all dolled up, LeBlanc actually looked quite believable as a woman, which probably shouldn’t be surprising considering his appeal as a man. However, the movie did not do well at the box office, but it was fun for viewers to see the beloved, masculine "Joey" cross-dressing in a film.

Jude Law

In 2009's Rage, Jude Law starred as mysterious Russian supermodel Minx, complete with a black bustier, short wig and a full face of makeup. In the film, a student filmmaker aspires to make a documentary about the important people in Manhattan using only his phone. However, the movie takes a twist and turns into a murder investigation.

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Other co-stars include Steve Buscemi, Judi Dench, Dianne Wiest, John Leguizamo and Lily Cole. Although it was widely panned by critics, Rage made history as the world’s first feature film to debut on mobile phones (split into seven different "episodes").

Barbra Streisand

Barbra Streisand showed her range as an actress, singer, director and writer in the 1983 film Yentl. She starred as the title character, an Ashkenazi Jewish girl living in Poland who decides to dress and live like a man to receive an education in Talmudic Law after her father dies.

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The film tackled a variety of themes, including rejecting gender roles, education rights and social expectations. In addition to other nominations for the film, Streisand became the first woman to receive a Golden Globe for Best Director.

Johnny Depp

The 2000 flick Before Night Falls is a biographical account of the life of gay Cuban poet and novelist Reinaldo Arenas. The film took a long, hard look at Cuba's ugly history of homophobia amid the Fidel Castro regime.

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Johnny Depp made quite an impression as a woman in his brief but sassy appearance as transvestite Bon Bon after Arenas is thrown into prison. On the other side of the coin, Depp made another cameo in the film as a tough jail guard. Although both the cameos were brief and a bit bizarre, viewers enjoyed seeing different sides of this famous actor.

Woody Harrelson

Adam Sandler's 2003 film Anger Management starred Jack Nicholson, Marisa Tomei and others. In the film, Sandler's character is sentenced to anger management therapy after he assaults an annoying flight attendant.

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In an interesting twist, the movie had a wild cameo from Woody Harrelson as Galaxia, a German drag queen prostitute who had a brief encounter with Sandler's character. It was strange but yet incredibly funny for viewers to see this tough guy dress up in a blonde wig and blood-red lipstick, even if it was only for a brief moment. Harrelson also appeared as Gary the security guard in the film.

Eddie Murphy

Eddie Murphy has gone through his share of transformations for films, but none of the others are quite like his work in the 1996 comedy The Nutty Professor. In the film, he played a total of seven characters — seven! — including two female ones (Anna Pearl Klump and Ida Mae Jensen). Obviously, making this film meant spending hours in makeup for Murphy.

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Still, he went on to reprise these roles in Nutty Professor II: The Klumps, which also starred Janet Jackson. The actor also dressed in drag for his 2007 film Norbit, playing the overweight and abrasive female character Rasputia.

Julie Andrews

The entertaining and witty 1982 film Victor/Victoria showcased Julie Andrews' famous acting and singing. However, she took things a step further by playing a gay Polish female impersonator in the film, a daring and bold move for the times.

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In an interview with Internet Shots, Andrews praised the film as being ahead of its time in terms of exploring gender identification. The film was nominated for several awards and won the Oscar for Best Original Score. Andrews also went on to win the Golden Globe for Best Actress in a Motion Picture Comedy or Musical.

John Travolta

After his appearances in Grease and Saturday Night Fever, John Travolta was praised for his dancing abilities. He brought those skills to the forefront again in his unconventional role as Edna Turnblad in the 2007 film Hairspray.

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Photo Courtesy: Hairspray/IMDb

Although he donned a plump bodysuit and a 60’s-style wig and clothing, the actor took his role very seriously. "Playing a woman attracted me," Travolta told The New York Times regarding the role. "Playing a drag queen did not. I didn’t want any winking or camping. I didn’t want it to be ‘John Travolta plays Edna.'"

Dustin Hoffman

Dustin Hoffman shined in his role as Dorothy Michaels, a made-up female his character, Michael Dorsey, desperately becomes to revive his acting career in 1982's Tootsie. The concept was practically unheard of at the time, but it was a hit, and the film became the second highest grossing movie of 1982 after E.T. the Extra-Terrestrial.

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Hoffman later revealed that he became emotional as he transformed into the character. "I know that if I met myself [as Dorothy] at a party, I would never talk to that character because she doesn't fulfill physically the demands that we're brought up to think women have to have," he revealed in an interview with the American Film Institute.

Adam Sandler

Like the other actors on this list, Adam Sandler has played a variety of different characters over the course of his career. However, the 2011 film Jack and Jill saw him decked out in drag, playing both a reserved ad executive and his annoying, boisterous twin sister.

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Jack and Jill was called "unfunny" and heavily panned by critics, even with stars like Katie Holmes, Al Pacino, Tim Meadows and David Spade among the cast. It became the first film to sweep the Razzies, "winning" in each category, including Worst Picture, Worst Actor and Worst Actress.

Gwyneth Paltrow

The 1998 film Shakespeare in Love starred Joseph Fiennes as famed playwright William Shakespeare alongside Gwyneth Paltrow as Viola De Lesseps. As Shakespeare develops Romeo and Juliet, Paltrow's character impersonates a man in order to play the lead in the production.

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The film was a massive success, winning seven Oscars, including Best Picture. Paltrow called the film, which also earned her an Oscar for Best Actress, a life-changing role. "It’s so clever in the way it tackles Shakespeare and all the inside jokes of show business," she shared with Variety.

Jamie Foxx

Jamie Foxx has played many comedic roles over the years, but none quite like his character Wanda Wayne on the sketch comedy show In Living Color. Foxx dressed in drag to play the character, who was described by many viewers and critics as the ugliest woman on the planet.

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Although the character was all about humor, Foxx took the role seriously. "You know what [show creator] Keenen Wayans taught me?" he said in an interview with Oprah Winfrey. "Take this time to work on your acting skills. Even in those little 30- or 40-second Ugly Wanda sketches, there's acting."

Kurt Russell

Kurt Russell starred alongside Sylvester Stallone in the 1989 film Tango & Cash. The movie centered around their characters, two rival LAPD narcotics detectives, who have to work together to clear their names after bogus murder charges are filed against them.

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Although he played a tough detective in the movie, Russell had a fun moment in the movie when he dressed up as a female stripper in a strip club to escape the cops. The brief scene had the actor in full drag, complete with a wig, huge rhinestone choker and sunglasses. It was undeniably a favorite moment for viewers during the film.

Liev Schreiber

For the 2009 film Taking Woodstock, Liev Schreiber dressed up in drag to play cross-dressing ex-Marine Vilma. The movie focuses on the memoirs of Elliot Tiber, who wrote about his Woodstock experience as well as being gay in New York in the 1960s.

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Photo Courtesy: Movieclips Classic Trailers/YouTube

Schreiber did his best to portray the shift in gay culture at the time. "It was exhilaratingly humiliating," he told Cleveland Scene during filming. "It’s different for actors because they’re a little more sophisticated when it comes to dress-up. But for some strange reason, there’s a tremendous energy in putting on women’s clothing."