The idea of cross-dressing as a theatrical staple has been around since medieval England. By 1598, when William Shakespeare presented As You Like It, which featured a cross-dressing heroine who disguises herself as a young boy and followed up with The Merchant of Venice (1600) as well as Twelfth Night (1602), on-stage cross-dressing had become the norm.

Silent-era films featured Charlie Chaplin (A Woman, 1915), Stan Laurel (Chasing the Chaser, 1925) occasionally dressing as women, and American actor, Wallace Beery, who appeared in a number of silent films as a Swedish woman. It wasn’t unusual to see the Three Stooges in drag, although at the time the idea of cross-dressing was largely executed for laughs. However, Alfred Hitchcock’s Murder! (1930) was no laughing matter. Soon after, movie star Greta Garbo starred in Queen Christina (1933), and Lionel Barrymore featured in The Devil Doll (1936): in both of those films, the actors appeared playing the opposite gender.

In 1953, Glen or Glenda was considered groundbreaking for its time. In 1959, Billy Wilder’s Some Like It Hot featured Jack Lemmon and Tony Curtis dressed as women. It caused an uproar from the Catholic League of Decency which deemed it “seriously offensive to Christian and traditional standards of morality and decency.” Nearly ten years later, in 1968, the film was considered groundbreaking in terms of helping to create a more inclusive and queer-friendly culture.

The 70s brought a different attitude to androgyny and cross-dressing when the likes of David Bowie and Iggy Pop became influential, not only in music but in fashion. It was the same era that produced Female Trouble, starring cross-dresser Divine, in 1974. The following year, The Rocky Horror Picture Show became a phenomenon worldwide. And in 1978, La Cage aux Folles earned a Golden Globe for Best Foreign Language Film.

The 80s films include Dressed to Kill (1980), the Oscar- and Golden Globe-winning movie Tootsie (1982), and Victor Victoria, in 1982, a remake of a German film from 1933 which saw Julie Andrews in the complicated role of a female impersonator, or as Andrews herself succinctly described her role, “a woman pretending to be a man, pretending to be a woman.” The role earned her a Best Actress Golden Globe in 1983. Barbra Streisand starred in Yentl (1983) and took home Oscar and Golden Globe trophies, and Harvey Fierstein rounded the decade with Torch Song Trilogy (1988).

In the 90s more films with transgender plot points include Nobody’s Perfect and Nuns on the Run (both 1990), Orlando (1992), and Mrs. Doubtfire (1993), one of Robin Williams’ biggest hits, which earned him a Golden Globe. There followed Farewell My Concubine (1993), The Adventures of Priscilla, Queen of the Desert (1994), and Ed Wood (1994), which last earned an Oscar and a Golden Globe for Martin Landau for Best Supporting Role. The following year To Wong Foo, Thanks for Everything! Julie Newmar earned two Golden Globes nods, and in 1996, The Birdcage was nominated for two Golden Globe awards. In the animated world, Mulan (1998) earned a Golden Globe nod, and in the same year Shakespeare in Love garnered both Oscar and Golden Globe awards; the following year, Boys Don’t Cry earned two Golden Globes and two Oscars. 1999 also brought All About My Mother, and in the same year audiences were treated to a performance by Robert De Niro taking singing lessons from a drag queen in Flawless.

The next decade began with Big Momma’s House, with Martin Lawrence going undercover as an FBI agent. This was followed by All the Queen’s Men (2001), Hedwig and the Angry Inch (2001), and The Triumph of Love, which starred Mira Sorvino who disguises herself as a young male scholar. In 2002, Rob Schneider starred in The Hot Chick. Other films of the time include Stage Beauty (2004), White Chicks (2004), Kinky Boots (2005), She’s the Man (2006), Peacock (2010) and Albert Nobbs (2011), which saw Glenn Close as a 19^th century Irishwoman who poses as a man to work as a butler in Dublin’s most elegant hotel. Then came The Boxtrolls (2014), The Danish Girl (2015) which earned three Golden Globes and four Oscars, Wig (2019), XY Chelsea (2019), The Panti Sisters, and more recently, Disclosure (2020).

Society has come a long way since those theatrical performances in medieval England, and with the popularity of TV shows like Ru Paul’s Drag Race, and the increasing acceptance of fluid sexual orientations, as well as a growing number of those undergoing gender reassignment, the idea of cross-dressing has become a part of our everyday life which is reflected in mainstream cinema.