Hollywood movies from early on found that audiences liked seeing people crossdressing. That includes scenes with men impersonating women, whether it was Bing Crosby and Danny Kay doing the musical number “Sisters” in “White Christmas” in the 1940s, or Tim Curry’s brilliant performance in “Rocky Horror Picture Show” who plays a “sweet transvestite from Transsexual, Transylvania.”
There have also been numerous movies with women dressing as men, in order to achieve some goal. Some of the great movies like that include “Yentl,” where Barbra Streisand dresses as Polish Jewish man in order to study the Talmud in early 20th century Europe; “Sahara,” where Brooke Shields disguises herself as man in order to compete in a car race in the African desert;” and “She’s the Man,” a movie based on William Shakespeare’s “Twelfth Night” in which Amanda Bynes dresses as a man to be on a soccer team to get revenge on another team. Even Disney has had crossdressers, including “Mulan,” where a young Chinese woman dresses as a soldier to help fight the Huns in place of her father.
However, there are some movies which are must-sees if you love drag shows. Here they are in no particular order (because they are all great!):
“To Wong Fong, Thanks for Everything! Julie Newmar.” Three drag queens change the lives of the people in a small town after their Cadillac breaks down on the way to Hollywood for the Miss Drag Queen of America pageant. The performances of Wesley Snipes, Patrick Swayze and John Leguizamo in this 1995 classic are hysterical.
“The Adventures of Priscilla, Queen of the Desert.” A 1994 comedy of three men traveling cross-country through Australia to perform a drag show in the outback. Guy Pearce and Hugo Weaving play two drag queens, while Terence Stamp is a post-operative male to female transsexual.
“The Birdcage.” A comedy of errors as Robin Williams who runs a drag bar in Miami and his hysterical partner/drag queen played by Nathan Lane try to help Williams’ son as he becomes engaged to the daughter of a priggish ultra-conservative U.S. senator. The dinner which Williams hosts for the senator and his wife are classic as Lane dresses as Williams’ wife.
“Victor, Victoria.” The 1982 musical stars Julie Andrews and focuses on all forms of transvestitism. Andrews is an impoverished soprano who then is presented as a gay Polish female impersonator. Great performances were seen by James Garner, Lesley Ann Warren, Robert Preston and Alex Karras.
“Kinky Boots.” Chiwetel Elijor’s character Simon is drag queen Lola in this hit musical who forges a friendship with straight-laced Charlie and helps save a small-town shoe factory in England. This 2005 British movie based on a true story is wonderful throughout, but the scene at the Milan fashion show is priceless.
Want more? Check out “Mrs. Doubtfire,” “Tootsie” and “Stage Beauty.”