You May Be Surprised by These Actors Who Have Performed in Drag
Dare to drag?
In 2023, anti-drag laws have become a subject of heated debate in 14 states across the nation, with Tennessee banning "adult cabaret performances."
From the ancient Greeks through Shakespeare to Milton "Uncle Miltie" Berle and beyond, the reliable burlesque trope of putting a man in a woman’s clothes — or vice versa — is as old as the theatre.
Whether is an elaborate suit or just a wig and eyeshadow, we wanted to take a look at some of the more recent examples of drag in cinema. So here are 22 actors who have sissied that walk or been a "king" for a day in their performances.
1. Flip Wilson ‘The Flip Wilson Show’
In the 1970s, Wilson made TV history as the first black performer to headline a hit variety show. With a quick flip of the wig and a flick of the hand, Flip Wilson transformed into the fabulous Geraldine Jones, leaving audiences in stitches with her hilarious antics. Among her many admirers was none other than the drag god RuPaul, who credited him as an early influence for his own trailblazing career.
2. Milton Berle in ‘Texaco Star Theatre’ (1948–1956)
“Mr. Television" was such a superstar in the 1940s, that people were rushing to buy the newly invented TV set just so they could see this kooky comedian in action. Milton Berle famously did drag in his variety television show called "Texaco Star Theatre," and is now widely known as “Television's First Drag Queen.” Uncle Miltie's (read: Auntie Mildred) daring acts saw him donning flamboyant dresses, wigs, and fruit-studded hats, pushing the boundaries of humor and challenging societal norms. In a bold move that showcased his commitment to the act, he even graced the cover of Newsweek magazine in 1949, stunningly decked out as the legendary Carmen Miranda.
3. Dustin Hoffman in 'Tootsie' (1982)
In the 1982 "Tootsie," Dustin Hoffman brilliantly brings to life Michael Dorsey, a neurotic actor driven to transform himself into a soap queen. Desperate for work, Michael takes on a daring disguise, cross-dressing as a woman named Dorothy Michaels. The transformation proves wildly successful, landing him job opportunities he could have never imagined. So if you are stuck in a job-hunting rut due, take a cue from Michael Dorsey and reinvent yourself.
4. Jack Lemmon & Tony Curtis in 'Some Like It Hot' (1959)
What makes Billy Wilder’s 1959 classic "Some Like It Hot" particularly delightful is how effortlessly Tony Curtis and Jack Lemmon exude elegance and chicness in their drag personas. As Jerry, Jack Lemmon's character finds himself on the run from the mob and joins an all-female band in disguise. Along the way, he unexpectedly falls in love with a nearsighted and infatuated millionaire. On the other hand, Tony Curtis plays the role of Joe, who embarks on a series of disguises throughout the film—ranging from a man on the run to a female saxophone player, and even as a wealthy heir to the Shell Oil fortune.
5. Tom Hanks in 'Bosom Buddies’
Before he was talking to a volleyball on a deserted island, the 25-year-old Tom Hanks made his breakthrough in the TV show "Bosom Buddies" (1980-1982), all pretty in pink. Hanks, along with Peter Scolari, stars as a pair of friends facing a housing predicament. After being kicked out of their apartment, they decide to pose as women and take on female identities to stay in a women's boarding house. Hilarity ensues as Hanks and Scolari navigate the challenges and humorous situations that arise from their unconventional living arrangements.
6. Robin Williams in 'Mrs. Doubtfire' (1993)
The late and great Robin Williams portrays Daniel Hillard, an immature father of three facing the loss of custody, after a bitter divorce in the beloved 1993 classic "Mrs. Doubtfire." To spend more time with his kids, Daniel opts for a drastic transformation involving a fatsuit, wig, and elaborate makeup. And, presto—He turns into an endearing British nanny, Euphegenia Doubtfire. Williams' cross-dressing artistry is as masterful as his acting, convincingly fooling everyone - from his distressed ex-wife to a bemused social worker and even a thirsty bus driver!
7. Wesley Snipes, Patrick Swayze, and John Leguizamo in 'To Wong Foo, Thanks for Everything! Julie Newmar' (1995)
In the 1995 film "To Wong Foo, Thanks for Everything! Julie Newmar," Wesley Snipes, Patrick Swayze, and John Leguizamo deliver standout performances in drag. The trio plays a group of drag queens who embark on a cross-country journey to participate in a national drag queen competition. The film beautifully showcases the art of drag, as Snipes, Swayze, and Leguizamo flawlessly transform into their fabulous alter-egos.
8.Barbra Streisand in ‘Yentl’ 1983
Barbra Streisand proves she's not just a woman in love, but a woman in drag too, portraying the bookworm named Yentl disguised as Anshel in "Yentl" (1983). Streisand wrote, directed, and starred in this captivating tale of a woman with the "soul of a man," challenging societal norms to thrive in a man's world. Streisand's groundbreaking work earned her the prestigious title of the first woman to win Best Director at the 1984 Golden Globes.
9. Tyler Perry in 'Madea' film series (e.g., "Madea's Family Reunion" - 2006)
With nothing more than a curly gray wig and a granny sweater, Tyler Perry worked his magic, and voilà - Madea Simmons burst onto the scene! This transformation sparked a surprising sensation that has only grown bigger over time, becoming the heart of a myriad of other projects. Perry's portrayal of the feisty Madea is a masterclass in cross-dressing comedy.
10. Cate Blanchett in 'I'm Not There' (2007)
In "I'm Not There," Cate Blanchett rocks the screen as Jude, capturing Bob Dylan's musical evolution from folk to electric rock. With her chameleon-like talent, Blanchett shines in every role, whether elves or cross-dressing. Her exceptional performance earned her an Oscar nomination for Best Supporting Actress.
11. Lucille Ball in 'I Love Lucy' (1951-1957)
In "I Love Lucy," the queen of comedy, Lucille Ball, takes cross-dressing to hilarious heights! The red-headed mischief-maker channels her inner Harpo Marx, in the episode titled "Lucy and Harpo Marx,” Lucy Ricardo finds herself in a zany escapade, donning the iconic look of the silent comedy genius.
12. Divine in 'Pink Flamingos' (1972)
Drag superstar Divine shines as the unforgettable ''Babs Johnson,' In this John Waters cult flick.' Embracing drag with unparalleled skill, Divine defends her title as "the filthiest person alive" with unapologetic gusto. It's a performance that's both audacious and uproarious, showcasing Divine's talent for pushing boundaries.
13. Nathan Lane In 'The Birdcage'
In the 1996 American adaptation of the French farce "La Cage aux Folles," Nathan Lane steals the show in "The Birdcage." Playing one-half of a drag-club-owning gay couple, Lane's character, Albert, finds himself in a hilariously tricky situation. To impress their future daughter-in-law's conservative family, Albert, and his partner must disguise themselves as a straight couple. As the laughter ensues, Albert ends up posing as a woman, leading to side-splitting comedic moments and a heartwarming exploration of love and acceptance.
14. Julie Andrews in 'Victor Victoria' (1982)
In the 1982 musical "Victor/Victoria," Julie Andrews shines as a female singer who cleverly disguises herself as a man in drag. The plot takes an amusing turn when Victoria finds herself romantically involved with a small-time crook, leading to a charming and hilarious adventure of mistaken identity and comedic situations.
15. Eddie Murphy in 'The Nutty Professor' (1996)
Eddie Murphy must have practically moved into the makeup room, in the 1996 remake of The Nutty Professor, given he dressed up for a total of seven roles—including most of the Klump family. But Murphy takes cross-dressing to the next level with his portrayal of the family's two matriarchs - Mama Klump and Grandma Klump.
16. John Travolta in 'Hairspray' (2007)
In the 2007 musical remake of John Waters' cult film "Hairspray," John Travolta fearlessly took on the role of the voluptuous and bubbly Edna Turnblad. Traditionally portrayed by male actors, the character of Edna has been brought to life by iconic figures like Divine in the original 1988 film and Harvey Fierstein in the 2002 Broadway rendition.
17.Alec Guinness in ‘Kind Hearts and Coronets’ (1949)
Alec Guinness's remarkable talent shines through in Robert Hamer's beloved Ealing Comedy, "Kind Hearts and Coronets," as he masterfully takes on a staggering eight distinct roles. However, it's his purse-lipped portrayal of Lady Agatha that remains an iconic image for the film.
18. Johnny Depp In 'Ed Wood'
In the unconventional collaboration between Johnny Depp and Tim Burton, "Ed Wood" shines as a particularly unique film. The story centers around the eccentric '50s B-movie director, Edward D. Wood, known as the worst director of all time. In "Glen or Glenda," a film inspired by his own experiences, he fearlessly explored the complexities of gender identity and personal expression. Johnny Depp's portrayal of this enigmatic figure brings depth and nuance to a captivating story that celebrates individuality and the power of artistic passion.
19. Michael J. Fox In 'Back To The Future Part II'
In "Back to the Future Part II," Michael J. Fox displays his exceptional range by not only playing the main character Marty McFly but also taking on the roles of Marty Jr. and Marlene, Marty McFly's troubled son and daughter.
20. Ryan Gosling In 'All Good Things (2010)
In the 2010 film "All Good Things," Ryan Gosling portrays a character inspired by the real-life case of cross-dressing killer Robert Durst. Clair E. Schuler, a Texas drag queen, revealed her involvement in helping the violent millionaire disguise himself as a woman to evade the repercussions of his crime.
21. Marlon and Shawn Wayans ‘White Chicks’ (2009)
The Wayans brothers transform themselves into the most over-the-top white women you could imagine. "White Chicks" is a side-splitting comedy where Marlon and Shawn Wayans take on the outrageous roles of undercover FBI agents going incognito as affluent socialites.
This article was produced and syndicated by MediaFeed.
