The days when male celebrities were expected to be macho alpha males are long gone. Today’s stars have to be in touch with their feminine sides and be able to demonstrate sympathy and empathy when it comes to their acting roles and to their press interviews.
The world is much more accepting of gay celebrities in the 21st century, and the sight of men wearing women’s clothing is not nearly as shocking as it might have been for our grandparents. Some famous people have even come out as transgender, perhaps the best-known example being Caitlyn Jenner, who transitioned in 2017.
Whether these male celebrities are wearing a dress for a film role or just because it suits their sense of style, there is no doubt that they all look good doing it.
18 Benedict Cumberbatch
Another actor best known for his serious roles, including Sherlock Holmes and Dr. Strange in the Marvel movies, Benedict Cumberbatch showed that he has a playful side when he dressed in drag to attend a London party. Having attended a boys’ school, the actor has said he is comfortable dressing as a woman, as he often had to play female characters on stage.
17 Ezra Miller
American actor Ezra Miller has followed firmly in the footsteps of David Bowie, celebrating his androgyny and saying that he doesn’t identify as a man or a woman. The We Need to Talk About Kevin star regularly wears feminine clothes on the red carpet, preferring high fashion outfits from cutting-edge designers like Givenchy and Valentino.
16 Marc Jacobs
Fashion designer Marc Jacobs doesn’t just enjoy wearing women’s clothes himself, he has also used male models to advertise the dresses he makes for female customers. The award-winning designer likes to play with gender roles when it comes to his catwalk shows and his collections and doesn’t look too bad in a dress either.
15 Adam Sandler
Adam Sandler may not have looked as good as Jude Law when he dressed as a woman to play his own sister in Jack and Jill, but he did look remarkably convincing as a girl! Sadly, the film itself was something of a flop, with Adam Sandler managing to win the Razzie for both Worst Actor and Worst Actress at the Golden Raspberry Awards in 2012.
14 Neil Patrick Harris
Versatile actor Neil Patrick Harris got his big break as a child star in Doogie Howser MD, but he is hardly recognizable in some of his recent stage roles. As well as playing Emcee in Cabaret, Harris also took on the role of the transgender Hedwig in Hedwig and the Angry Inch, for which he won a Tony Award in 2014.
13 Tim Curry
Perhaps the most iconic example of cross-dressing in the movies is Tim Curry as the flamboyant Dr. Frank-N-Furter in The Rocky Horror Picture Show. Curry made the role his own and managed to look sensational strutting around the movie set in women’s underwear. Fans of the show even dress as Dr. Frank-N-Furter when they go to watch screenings of the film!
12 Billy Porter
Broadway performer and star of TV series Pose Billy porter loves to dress in flamboyant and feminine outfits, including this unique combination of tuxedo and ball gown which he wore to the 2019 Academy Awards and a colorful pink and red chiffon outfit which stole the show at the 2019 Tony Awards.
11 Jason Isaacs
British actor Jason Isaacs is best known for playing Lucius Malfoy in the Harry Potter series of films, but long before he was a follower of he who must not be named, he was embracing his feminine side when he played drag queen Chaz in the 2001 romantic comedy Sweet November and looked very good doing it.
10 Jude Law
Another Brit actor who transformed himself into a woman for a film role was Jude Law, who played Minx in the 2009 film Rage alongside Dame Judi Dench. Heartthrob Law was almost unrecognizable in the movie, which made history as the first feature film to be made entirely using cell phone cameras.
9 Jared Leto
A much more impressive cross-dressing performance in a much more impressive film came from Jared Leto in The Dallas Buyers Club. Leto, who won a Best Supporting Actor Oscar for playing trans woman Rayon, managed to look fantastic despite the fact that his character was terminally ill throughout the whole film.
8 Liev Shreiber
Actor Liev Schreiber obviously feels very comfortable dressing in female clothing, as he has dressed as a woman in not one but two different films. He played transgender woman Chris in the 1994 comedy Mixed Nuts and gay transvestite Vetty Von Vilma in the 2009 film Taking Woodstock and looked fantastic in both movies.
7 Cillian Murphy
Cillian Murphy played transgender woman Patricia Braden in the 2005 film Breakfast on Pluto, adapted from the novel of the same name by Patrick McCabe. The Irish actor was brilliant in the challenging role, and as an added bonus, looked absolutely stunning in the stylish outfits which his character was required to wear.
6 Sir Ian McKellen
Sir Ian McKellen isn’t just acting royalty, and a powerful evil mutant in the X-Men films to boot, but he also has a fantastic sense of humor and was more than happy to dress up in a frock to play pantomime dames in the annual Christmas play at the Old Vic theatre in London.
5 Patrick Swayze
The 1995 film To Wong Foo starred three Hollywood leading men as New York drag queens who get stuck in a small town on their way to Los Angeles. Patrick Swayze, Wesley Snipes, and John Leguizamo might not have been the obvious choice to play award-winning drag queens, but they all pulled off their roles with aplomb.
4 Jonathan Van Ness
Makeover show Queer Eye for the Straight Guy has made a triumphant return to the small screen thanks to Netflix. The new stars of the show include hairstylist Jonathan Van Ness, who loves to show off his feminine side on his red carpet outfit, including this stylish little black dress at the 2018 Emmys.
3 Dustin Hoffman
One of the most iconic drag performances in Hollywood history came from Dustin Hoffman in the 1982 comedy Tootsie. Hoffman played an out-of-work actor who dressed as an older woman in order to win a role on a daytime soap opera. Thanks to some serious time in the make-up chair, Hoffman made a rather convincing Dorothy Michaels.
RuPaul is the undisputed queen of drag, having enjoyed a long career on the stage and screen. Having started his career in New York in the 1980s, RuPaul has now become a household name thanks to the reality TV show Rupaul’s Drag Race which aims to find the best new drag queens – and which features the presenter himself in a number of stunning outfits.
1 Gael Garcia Bernal
Mexican actor Gael Garcia Bernal made a very convincing woman in Bad Education, the 2004 film by Spanish director Pedro Almodovar. In the film, Bernal’s character, Zahara, even manages to fool an old school friend, a premise that was totally believable given how good he looked dressed as a woman.
Sources: NY Times, Insider, Independent, ABC, Hollywood Reporter