Top 10 Greatest Cross-Dressing Movie Roles
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Some were loveable, some were laughable, and some were downright unrecognizable. Welcome to WatchMojo.com and today we’re counting down our picks for the top 10 cross-dressing roles.
For this list, we’ve decided to stay away from more serious cross-dressing roles and have instead focused on more comedic films that made us laugh, giggle and sometimes cringe.
#10: Joyce Hyser as Terry Griffith
“Just One of the Guys” (1985)
In this enjoyable ‘80s romp, Hyser plays a teenage girl on a mission to prove her skills as a journalist – by dressing as a teenage boy. Turned down for an internship supposedly due to her good looks, she’s out to demonstrate that she’s more than just a pretty face. She makes a convincing teenage boy AND teenage girl, making her performance fairly spot-on. #9: Johnny Depp as Ed Wood
“Ed Wood” (1994)
As a self-proclaimed “transvestite,” Ed Wood enjoyed the occasional poodle skirt and heels combo. Johnny Depp’s turn as the cult film director offered up the perfect amount of pep, perkiness, and pleasant disposition, adding humor and the occasional dash of gravitas to the role. The film garnered rave reviews, and even though it’s not a huge plot-point, we think Depp’s cross-dressing performance helped it along.#8: Shawn & Marlon Wayans as The Wilson Sisters
“White Chicks” (2004)
The Wayans brothers play two FBI detectives who go undercover as a couple of socialite sisters in this extreme case of cross-dressing gone wild. The brothers’ transformation into a pair of white chicks is completed with full-body make-up, contact lenses, nasal prosthetics and wigs. It’s pretty convincing in a creepy, uncomfortable, pseudo-racist kind of way. #7: Martin Lawrence as Big Momma
“Big Momma’s House” (2000)
In this gender-swapping film, Martin Lawrence plays Malcolm Turner, yet another FBI agent who must go undercover as a woman to unravel a criminal scheme. Lawrence dons a fat suit and undergoes hours of makeup to be turned into Big Momma, a southern matriarch and the key to cracking the bank robbery case. Shenanigans ensue, and Lawrence eventually ends up solving the case and winning the girl at the end cause it’s what’s on the inside that counts. #6: Nathan Lane as Mrs. Coleman
“The Birdcage” (1996)
Lane plays Albert, one half of a gay couple who goes all out to impress a conservative, strait-laced family. Albert takes on the role of “Mrs. Coleman,” a traditional wife and mother who must convince the parents of his boyfriend’s son’s fiancée that he and his partner are a conventional, right-wing American family. Of course, there’s lotsa confusion, but Lane’s performance as a middle-aged married woman is a standout moment in the film.#5: Patrick Swayze, Wesley Snipes & John Leguizamo as Drag Queens
“To Wong Foo, Thanks for Everything! Julie Newmar” (1995)
These three men deviate entirely from their ultra-macho, action-hero personas with their performance as three drag queens stranded in a small town. Headed to a drag show pageant when their car breaks down, Vida Boheme, Noxeema Jackson and Chi-Chi Rodriguez inject a little fabulousness into the town before taking off in a trail of glitter and fierceness. We may have cringed a fair amount, but these performances are undeniably entertaining.#4: Tim Curry as Dr. Frank N. Furter
“The Rocky Horror Picture Show” (1975)
Curry plays this “sweet transvestite” in his role in this 1970’s cult classic. Wearing tons o’ makeup, heels and garters, Curry struts and performs the iconic character that garnered a cult following unparalleled in movie history. His performance as the swings-both-ways doctor is memorable not just cause of the lipstick, but also for his mischievous and entertaining delivery. #3: Tony Curtis & Jack Lemmon as Josephine & Daphne
“Some Like It Hot” (1959)
Curtis and Lemmon pair up in this classic comedy as a couple of jazz musicians hiding out from the mob. After witnessing the infamous Saint Valentine’s Day Massacre, the two decide it would be prudent to dress up as ladies and hit the road with an all-female band. Maintaining the farce becomes difficult, however, when they encounter the sultry and irresistible Miss Sugar Kane.#2: Robin Williams as Mrs. Euphegenia Doubtfire
“Mrs. Doubtfire” (1993)
Williams plays an unemployed actor and devoted father who will do anything to spend more time with his kids – he’ll even wear a dress and get a job as their nanny. His makeover is so thorough not even his own children recognize him, and eventually he wins their hearts as their strict yet loveable caregiver, Mrs. Doubtfire. By the end of the movie, he’s found out, but finds a less….strange way to see his kids. Before we unveil our number one pick, here are a few honorable mentions:
- Gwyneth Paltrow as Thomas Kent “Shakespeare in Love” (1998)
- Barbra Streisand as Anshel “Yentl” (1983)
- Jaye Davidson as Dil “The Crying Game” (1992)
- Ming-Na Wen as Fa Ping “Mulan” (1998)
#1: Dustin Hoffman as Dorothy Michaels
“Tootsie” (1982)
Michael Dorsey can’t land an acting job for the life of him, so he takes matters into his own hands and decides to try his luck as a woman. These efforts are complicated by his relationships with the women is his life, the suitors interested in his new persona, and his sudden jump into stardom. Hoffman’s role as Dorothy Michaels was so spot-on; it led to an Oscar nomination.Do you agree with our list? What’s your favorite cross-dressing role? For more entertaining Top 10s published daily, be sure to subscribe to WatchMojo.com.
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