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