What do Tom Hanks, Wesley Snipes, and Barbra Streisand have in common? Not just their blockbuster filmographies, but each has played a role that required a full drag makeover sometimes for laughs, sometimes for drama, and quite often to make a statement. These are more than simply a wardrobe change; they’re pop culture records of when Hollywood was daring enough to mess around with gender and identity on the screen.
From Golden Globe-winning roles to cult favorites that still pack midnight movie houses, drag has been an ever-present thread throughout the history of film and television. Some used it to make an in, some to challenge stereotypes, and others just for kicks. Below is a look back at the shocking, unforgettable, and sometimes raunchy times A-listers traded their everyday appearance for wigs, stilettos, and a whole new persona.
1. Tom Hanks in ‘Bosom Buddies’
Tom Hanks became famous in the pre-Oscar era through the early ’80s sitcom “Bosom Buddies,” where he played a man who impersonated a woman in an attempt to get cheap accommodation in a women’s boarding house. Hanks battled through humorously chaotic times in dresses and makeup alongside Peter Scolari and proved the charm and timing that would define his career. The concept of the show itself may have been fanciful, but it raised questions about gender presentation years before it was something that mainstream TV would be able to explore that debate.
2. Barbra Streisand in ‘Yentl’
Barbra Streisand didn’t just perform in “Yentl” in 1983 she wrote, directed, and produced the story of a young Jewish woman who disguises herself as a man so that she can study religious texts that women are forbidden to read.
Her take on Yentl/Anshel was a revolutionary one, earning her the distinction of being the first female Best Director at the Golden Globes. The combination of romance, identity, and rebellion in the film remains one of her career highlights, demonstrating that drag cinema is as emotional as it is transfigurative.
3. Robin Williams in ‘Mrs. Doubtfire’
Few drag roles are more iconic than Robin Williams’ turn in the 1993 blockbuster “Mrs. Doubtfire.” As Daniel Hillard, a dad who wants to stay close to his children after a break-up so badly that he decides to become the stern but loving British nanny Euphegenia Doubtfire, Williams employed prosthetics, a wig, and impeccable comedic timing to deliver a performance that was both side-splitting and endearing, and turn the film into an instant family favorite.
4. Wesley Snipes, Patrick Swayze & John Leguizamo in ‘To Wong Foo’
In the 1995 road comedy “To Wong Foo, Thanks for Everything! Julie Newmar,” Patrick Swayze, Wesley Snipes, and John Leguizamo play drag queens traveling cross-country to a pageant. Their acting and makeup introduced drag culture to mainstream movies with panache and dignity. The film was a celebration of self and community and has become a cult classic that continues to popular today.
5. Dustin Hoffman in ‘Tootsie’
In “Tootsie” (1982), down-on-his-luck actor Michael Dorsey was portrayed by Dustin Hoffman as he becomes Dorothy Michaels, a soap opera actress, in disguise in order to work. Not only does the character help revitalize his acting career in the movie but also forces his character to cope with sexism in a different light. Both humorous and socially conscious, Hoffman’s performance earned him critical acclaim and a permanent place in the history of film.
6. Nathan Lane in ‘The Birdcage’
Sheer fun is Nathan Lane as Albert in the 1996 comedy “The Birdcage.” As one half of a Miami drag club-owning couple paired with Robin Williams, Lane’s character goes the whole drag route in an effort to impress his potential in-laws fierce conservatives. The result is a snowballing of comedic set pieces that also convey a message about love, acceptance, and the folly of prejudice.
7. Julie Andrews in ‘Victor/Victoria’
Julie Andrews acted in a gender-bending triple role in the 1982 musical “Victor-Victoria,” an actress pretending to be a man and who impersonates a woman. It was a critical and box-office hit, earning Andrews an Oscar nomination and proving her adeptness at combining elegance, wit, and vocal power in a single unforgettable performance.
8. John Travolta in ‘Hairspray’
John Travolta donned a fatsuit, wig, and heels for the 2007 musical re-make of “Hairspray,” where he performed Edna Turnblad, a kind, timid mom who has to learn to embrace change. The role of Edna, traditionally played by men, allowed Travolta the opportunity to have a campy good time while still being able to offer up a warm, motherly presence whose presence kept the film’s message of acceptance grounded.
9. Jack Lemmon & Tony Curtis in ‘Some Like It Hot
Billy Wilder’s 1959 “Some Like It Hot” remains the most fashionable, most wittiest drag comedy ever made. Jack Lemmon and Tony Curtis, on the run from gangsters, disguise themselves as women in a female band. Their chemistry with Marilyn Monroe and the film’s acerbic dialogue turned it into an overnight classic of Hollywood legend and a reminder that drag has been making people laugh for decades.
These performances show that drag in Hollywood is no joke or shock instead, it’s a stylistic tool that can be utilized to reveal vulnerability, disturb norms, and create legendary characters. To make us laugh, to drive the drama, or simply for spectacle, these celebrities wore someone else’s shoes literally and left a lasting dent in pop culture.
