Fifty Most Iconic Gender Benders of All Time (2024)

Shakespeare’s Sisters (ca. 1600)Shakespeare’s comedic heroines — Viola/Cesario in Twelfth Night; Rosalind/Ganymede in As You Like It; and Portia... Shakespeare’s Sisters (ca. 1600)Shakespeare’s comedic heroines — Viola/Cesario in Twelfth Night; Rosalind/Ganymede in As You Like It; and Portia/Balthazar in The Merchant of Venice — challenge gender roles to secure their desired romantic outcomes. But their eventual return to “women’s weeds” makes the lasting effects of their transgression questionable, a fact further complicated by the stock Elizabethan practice of casting boy actors to play female roles. Photo: Bettmann/Corbis

Chevalier d'Éon, Charles Geneviève Louis Auguste André-Timothée d'Éon de Beaumont (1728–1810)The French diplo... Chevalier d'Éon, Charles Geneviève Louis Auguste André-Timothée d'Éon de Beaumont (1728–1810)The French diplomat was a lifelong transvestite. Speculation about the Chevalier ran rampant, with bets on his gender placed on the London Stock Exchange. Sometimes d'Éon self-identified as male, other times as female. But the public demanded proof. Eventually, the London courts, upon the testimony of a surgeon, deemed him a woman. When she returned to France, the Chevalier was restyled as the Chevalière and was stripped of her military uniform. d'Éon was forced to live the remainder of her life as a woman, when upon her death it was revealed that she was anatomically he. Photo: Bettmann/Corbis

Dustin Hoffman in Tootsie (1982)Hoffman plays out-of-work actor Michael Dorsey who poses as actress Dorothy Michaels to land a part, falling fo... Dustin Hoffman in Tootsie (1982)Hoffman plays out-of-work actor Michael Dorsey who poses as actress Dorothy Michaels to land a part, falling for his co-star Julie Nichols (Jessica Lange) in the process. Trading khakis for “a dynamite red sequined dress,” he eventually doffs the wig to get the girl. But in the end, he can’t quite give up Dorothy’s wardrobe; he resists when Lange asks to borrow his yellow Halston. Photo: LGI Stock/Corbis

Marlene Dietrich in Morocco (1930)In top hat and tails, Dietrich gets dapper in Morocco. As nightclub singer Amy Jolly, she wins over a hostil... Marlene Dietrich in Morocco (1930)In top hat and tails, Dietrich gets dapper in Morocco. As nightclub singer Amy Jolly, she wins over a hostile crowd and even steals a kiss from a woman in the audience before slinking offstage. A superstar and gay icon is born. Photo: Everett Collection

Shi Pei Pu (1938–2009)Singer, spy, butterfly. Shi Pei Pu was a Chinese opera star when he met Frenchman Bernard Boursicot in 1964. Shi convinced... Shi Pei Pu (1938–2009)Singer, spy, butterfly. Shi Pei Pu was a Chinese opera star when he met Frenchman Bernard Boursicot in 1964. Shi convinced Boursicot that he was a woman, and they began an affair that continued (on and off) for twenty years. In that time, Boursicot passed Shi sensitive documents and Shi produced a son she claimed was his. Eventually, they were arrested for espionage and Shi’s gender was revealed. Intrigued by the culture clash of East and West, masculine and feminine, playwright David Henry Hwang dramatized the affair in M. Butterfly. Photo: Phillippe Bouchon/AFP/Getty Images

John Cameron Mitchell in Hedwig and the Angry Inch (2001)Riffing on Plato’s Symposium and inspiring a tattoo symbolizing LGBT self-acceptance, ... John Cameron Mitchell in Hedwig and the Angry Inch (2001)Riffing on Plato’s Symposium and inspiring a tattoo symbolizing LGBT self-acceptance, John Cameron Mitchell’s Hedwig and the Angry Inch has become a queer film classic. To escape East Berlin, Hansel undergoes a botched sex change (becoming Hedwig with the “angry inch”). Hedwig goes from trailer park housewife to glam rock glitter queen before baring it all — ultimately realizing that the love she was looking for was staring her back in the mirror all along. Photo: Fine Line Features/Everett Collection

Terence Stamp, Hugo Weaving, and Guy Pearce in The Adventures of Priscilla, Queen of the Desert (1994)A road trip buddy comedy in drag, The Adv... Terence Stamp, Hugo Weaving, and Guy Pearce in The Adventures of Priscilla, Queen of the Desert (1994)A road trip buddy comedy in drag, The Adventures of Priscilla, Queen of the Desert stars Hugo Weaving, Guy Pearce, and Terence Stamp as Mitzi, Felicia, and Bernadette — two drag queens and a transsexual on their way to a show in the middle of nowhere. Confronting hom*ophobia along the way, they fulfill Felicia’s lifelong “co*ck in a frock on a rock” fantasy, by climbing King’s Canyon in full showgirl drag. Photo: Ronald Grant Archive/Everett Collection

Divine (1945–1988)Harris Glenn Milstead met John Waters in 1963, when both were high school students in Baltimore. Waters dubbed his muse “Divin... Divine (1945–1988)Harris Glenn Milstead met John Waters in 1963, when both were high school students in Baltimore. Waters dubbed his muse “Divine” after the character in Jean Genet’s Our Lady of the Flowers, and described her as “the most beautiful woman in the world, almost.” The duo collaborated on nine films that “battle[d] against the tyranny of good taste” and introduced the world to Ricki Lake. Photo: John Springer Collection//Corbis

Amanda Lepore (b. 1967)When she got her sex change, Lepore “was just wishing [she] could be a pretty girl working in a mall.” She’s since left t... Amanda Lepore (b. 1967)When she got her sex change, Lepore “was just wishing [she] could be a pretty girl working in a mall.” She’s since left the food court behind. Self-proclaimed “number one transsexual in the world,” Lepore is plastic perfection. A nightlife fixture, M.A.C. model, and David LaChapelle muse, her looks have become her business. Photo: Janet Mayer / Splash News/Corbis

k.d. lang (b. 1961)Canadian crooner k.d. lang has been called “the Warren Beatty of lesbians” by (Beatty ex) Madonna and appeared on the cover o... k.d. lang (b. 1961)Canadian crooner k.d. lang has been called “the Warren Beatty of lesbians” by (Beatty ex) Madonna and appeared on the cover of Vanity Fair— in pinstripes, getting a hot shave from Cindy Crawford. Lang winked at her penchant for menswear with her 1997 album drag. Photo: Neal Preston/Corbis

Milton Berle (1908–2002)Uncle Miltie was “a man who wasn’t afraid of a dress.” A Borscht Belt veteran, Berle became the host of Texaco Star Thea... Milton Berle (1908–2002)Uncle Miltie was “a man who wasn’t afraid of a dress.” A Borscht Belt veteran, Berle became the host of Texaco Star Theateron NBC in 1948. His vaudeville antics and visual comedy were perfectly suited to the new medium and earned him the nickname “Mr. Televison.” Berle became TV’s first breakout star and its best salesman, with TV sales skyrocketing as audiences raced to see what outrageous getup Uncle Miltie would wear next. Photo: Gregory Pace/Corbis

Edward Hyde, Lord Cornbury, later Third Earl of Clarendon (1661–1723)A portrait of Edward Hyde, Lord Cornbury — the governor of the royal provin... Edward Hyde, Lord Cornbury, later Third Earl of Clarendon (1661–1723)A portrait of Edward Hyde, Lord Cornbury — the governor of the royal provinces of New York and New Jersey from 1702–1708 — hangs in the New York Historical Society. He’s wearing a blue gown and a tiara. Contemporary accounts corroborate that Hyde often wore women’s clothing; he claimed, as Queen Anne’s relative and representative, he was doing his best to represent her faithfully. Historians question whether the rumors were politically motivated gossip, but art historians maintain that the portrait is credible rather than caricature. Photo: Bettmann/Corbis

Katharine Hepburn in Sylvia Scarlett (1935)Known for wearing pants onscreen and off, long before it was fashionable for women to do so, Kathari... Katharine Hepburn in Sylvia Scarlett (1935)Known for wearing pants onscreen and off, long before it was fashionable for women to do so, Katharine Hepburn went all-out drag in Sylvia Scarlett. In her first film with Cary Grant, Hepburn played a female con artist disguised as a boy to evade the authorities. A critical and commercial flop, Sylvia Scarlett helped land Hepburn on a list of actors considered “box office poison” by theater owners. Photo: Everett Collection

Lady Gaga As Jo Calderone (2010)Jo Calderone is an auto mechanic from Palermo, Sicily, who’s been on the cover of Vogue Hommes Japan. He’s also ... Lady Gaga As Jo Calderone (2010)Jo Calderone is an auto mechanic from Palermo, Sicily, who’s been on the cover of Vogue Hommes Japan. He’s also Lady Gaga. Following in the footsteps of Annie Lennox, Gaga attended the 2011 MTV VMAs as her greaser alter ego and stayed in character all night long — from her "Yoü and I” performance to awkwardly flirting with Britney Spears, with multiple men’s room visits in between. Photo: Jason Merritt/Getty Images

Candy Darling (ca. 1944–1974)Actress and pre-op transsexual Candy Darling is best known as a Warhol “superstar.” Appearing in Flesh (1968) and W... Candy Darling (ca. 1944–1974)Actress and pre-op transsexual Candy Darling is best known as a Warhol “superstar.” Appearing in Flesh (1968) and Women in Revolt (1971), she was immortalized in the Velvet Underground’s “Candy Says ” and Lou Reed’s “Walk on the Wild Side.” Diagnosed with cancer, Darling staged one last cinematic moment, posing for photographer Peter Hujar’s “Candy Darling on her Deathbed” — an iconic image that resurfaced as the cover art of Antony and the Johnsons’ I Am a Bird Now. Photo: Bettmann/Corbis

Candy (2009)Launched in 2009, and named for Candy Darling, Candy magazine is the pet project of independent creative director and publisher Luis... Candy (2009)Launched in 2009, and named for Candy Darling, Candy magazine is the pet project of independent creative director and publisher Luis Venegas. Billing itself as the “world’s first transversal style magazine,” Candy covers have included James Franco (as a Nan Kempner look-alike smoking in le Smoking) and Chloë Sevigny (as Terry Richardson shot by Terry Richardson). With photography by Bruce Weber and David Armstrong, the limited-edition annual has been selling out at $55/issue. Photo: Candy Magazine

Claude Cahun (1894–1954)Born Lucy Schwob, Surrealist artist Claude Cahun adopted her androgynous pseudonym in 1917. Called “one of the most curi... Claude Cahun (1894–1954)Born Lucy Schwob, Surrealist artist Claude Cahun adopted her androgynous pseudonym in 1917. Called “one of the most curious spirits of our time” by André Breton, her work challenges identity through self-portraiture. With her lover Suzanne Malherbe (who went by Marcel Moore), Cahun also created anti-Nazi propaganda during WWII. Photo: Barbara Hammer Prod./Everett Collection

Anne Bonny and Mary Read (early 1700s)Lady pirates hoist the mast. The wife of Calico Jack Rackham, Anne Bonny kept her gender hidden as a membe... Anne Bonny and Mary Read (early 1700s)Lady pirates hoist the mast. The wife of Calico Jack Rackham, Anne Bonny kept her gender hidden as a member of her husband’s crew, until she fell for another seaman who, unbeknownst to her, was also a cross-dressed woman. Both Bonny and Mary Read had been raised as boys since childhood — Bonny was disguised to hide her illegitimacy and Read was substituted for a deceased brother. Photo: Hulton Archive/Getty Images

Barbra Streisand in Yentl (1983)Mocked by critics as “Tootsie on the Roof,” Yentl is another cross-dress-for-success narrative. In order to stu... Barbra Streisand in Yentl (1983)Mocked by critics as “Tootsie on the Roof,” Yentl is another cross-dress-for-success narrative. In order to study the Torah, Yentl trades her apron for a suit and lops off her hair to wear a yarmulke. Disguising herself as a boy, she falls for another yeshiva student but ultimately chooses scholarship over love. Photo: David James/Sygma/Corbis

Boy George (b. 1961)“Karma Chameleon” Boy George turned into a beautiful cover girl for U.K.Cosmopolitan’s December 1984 issue. Tempering ... Boy George (b. 1961)“Karma Chameleon” Boy George turned into a beautiful cover girl for U.K.Cosmopolitan’s December 1984 issue. Tempering girliness with his Boy-ish moniker, George was also known to appear in a nun’s habit and in Hasidic garb. His trademark look helped anchor Jean-Paul Gaultier’s pop star inspired spring 2013 collection. Photo: Corbis

Andy Warhol (1928–1987)Warhol admired “the boys who spend their lives trying to be complete girls” and often attended parties in drag. Flipping ... Andy Warhol (1928–1987)Warhol admired “the boys who spend their lives trying to be complete girls” and often attended parties in drag. Flipping his silver wig for blonde, red, and black ones, he began a series of Self Portrait in Drag Polaroids in 1981, and continued the project with Christopher Makos as Altered Images. Their Altered Images recall Man Ray’s twenties portraits of Marcel Duchamp as his female persona, Rrose Sélavy. Photo: Nancy R. Schiff/Hulton Archive/Getty Images

Mr. Brainwash “Spock Marilyn Monroe” (2009)Mr. Brainwash borrowed Warhol’s silkscreens and wigs for his “Spock Marilyn Monroe.” The nom de a&eac... Mr. Brainwash “Spock Marilyn Monroe” (2009)Mr. Brainwash borrowed Warhol’s silkscreens and wigs for his “Spock Marilyn Monroe.” The nom de aérosol of Thierry Guetta, Mr. Brainwash is a Banksy protégé (some say hoax/alter ego) profiled in Exit Through the Gift Shop. Taking Warhol’s celebrity obsession and fetish for replication a step further, and plagiarizing Shepherd Fairey’s mash-up of Monroe and André the Giant, Mr. Brainwash places Marilyn’s coif on everyone from Spock to Madonna, Obama, and Michael Jackson. Photo: austinevan/flickr

Jeanne d'Arc, The Maid of Orléans (ca. 1412–1431)Like the numerous transvestite female saints of the Middle Ages (Pelagia, Wilgefortis, a... Jeanne d'Arc, The Maid of Orléans (ca. 1412–1431)Like the numerous transvestite female saints of the Middle Ages (Pelagia, Wilgefortis, and Eugenia among them), Joan of Arc assumed masculine privilege as a matter of faith. After a visitation from the angels, she cropped her hair and donned men’s clothing. Crossing class as well as gender lines, she styled herself as a knight and took up arms. Joan’s cross-dress was emblematic of her defiance; when she was tried by the Inquisition, it was for charges of transvestism rather than heresy. Photo: adoc-photos/Corbis

Christine Jorgensen (1926–1989)With the New York Daily News headline “Ex-GI becomes Blonde Beauty” in 1952, Christine Jorgensen became the first... Christine Jorgensen (1926–1989)With the New York Daily News headline “Ex-GI becomes Blonde Beauty” in 1952, Christine Jorgensen became the first widely known transsexual. Gender reassignment surgery had been pioneered in Germany in the twenties, but Jorgensen was the first to go public. Beginning her transition with hormone therapy in Copenhagen, she completed surgical reassignment in the states. A lifelong advocate for transsexuals, Jorgensen helped educate the public on the difference between gender identity and sexual preference. Photo: Bettmann/Corbis

Brandon Teena (1972–1993)Brandon Teena was a victim of incest who began identifying as a male in adolescence and was living as a pre-op trans ma... Brandon Teena (1972–1993)Brandon Teena was a victim of incest who began identifying as a male in adolescence and was living as a pre-op trans man when he was murdered in 1993. When an arrest report in the newspaper outed Brandon Teena as Teena Brandon, he was violently raped by transphobic acquaintances. And when he reported the assault to police, Brandon’s attackers shot and killed him. Memorialized in the biopic Boys Don’t Cry, Hilary Swank’s portrayal of Brandon earned her an Oscar. Photo: Bureau L.A. Collection/Sygma/Corbis

T. J. Jourian in TransGeneration (2005)Self-identified “pansexual queer Middle Eastern transman” T.J. Jourian was one of four transgendered col... T. J. Jourian in TransGeneration (2005)Self-identified “pansexual queer Middle Eastern transman” T.J. Jourian was one of four transgendered college students profiled in the Sundance Channel series TransGeneration. At the time of filming, Jourian — a Cypriot of Armenian descent — was a Fulbright Scholar and grad student at Michigan State. After the show, Jourian was interviewed by a baffled Larry King (“Wait a minute. Are you a girl?”) — an exchange later parodied by SNL with Natalie Portman playing T.J. Photo: Sundance Channel

Paris Is Burning (1990)While Madonna taught the masses to “strike a pose,” Willi Ninja and Pepper LeBeija gave Jennie Livingston a master class ... Paris Is Burning (1990)While Madonna taught the masses to “strike a pose,” Willi Ninja and Pepper LeBeija gave Jennie Livingston a master class on how to vogue. Livingston’s documentary Paris Is Burning chronicles the burgeoning ballroom scene of the eighties and nineties. In New York, drag balls provided a surrogate family and an escapist fantasy for disenfranchised Black and Latino gay and transgendered “children,” and taught them that being themselves was how “to be real.” Photo: Off White Productions/Everett Collection

RuPaul (b. 1960)“Supermodel of the World,” RuPaul Charles is enjoying a second act on the small screen. Introducing the next generation of gende... RuPaul (b. 1960)“Supermodel of the World,” RuPaul Charles is enjoying a second act on the small screen. Introducing the next generation of gender-bending superstars (Manila, Raja, and Latrice, oh my!) on RuPaul’s Drag Race and helping real women find their femme on RuPaul’s Drag U; it’s looking like the Glamazon won’t “sashay away” anytime soon. Photo: Mitchell Gerber/Corbis

Billy Tipton (1914–1989)Born Dorothy Lucille Tipton, jazzman Billy Tipton lived for more than 50 years as a man. Billy never legally married but... Billy Tipton (1914–1989)Born Dorothy Lucille Tipton, jazzman Billy Tipton lived for more than 50 years as a man. Billy never legally married but, over the years, as many as five women identified as “Mrs. Tipton.” He told his wives that a catastrophic car accident had left him sterile. With the fifth, Kitty Oakes, he raised three adopted sons. A funeral director finally revealed Tipton’s secret to his family. One of his sons remarked: “He’ll always be Dad to me.” Photo: Tops Records

David Bowie (b. 1947)The original ambisexual androgynous alien, David Bowie “fell to Earth” and put on a frock. It’s no surprise John Lennon cal... David Bowie (b. 1947)The original ambisexual androgynous alien, David Bowie “fell to Earth” and put on a frock. It’s no surprise John Lennon called Bowie’s music “rock and roll with lipstick on.” Satirizing gender inequity with his “Boys Keep Swinging” video, Bowie dressed up to sing backup (for himself), walking the runway and keeping time as a blonde, a brunette, and a redhead. Photo: BILL ORCHARD / Rex Features/Everett Collection

Joyce Hyser in Just One of the Guys (1985)Just One of the Guys is Twelfth Night High. A loose adaptation of Shakespeare’s comedy, the mov... Joyce Hyser in Just One of the Guys (1985)Just One of the Guys is Twelfth Night High. A loose adaptation of Shakespeare’s comedy, the movie has aspiring journalist Terri going undercover to expose sexism. After going “where no woman has gone before” (the boys’ locker room), Terri has to reveal herself for love. Just One of the Guys was itself cross-dressed as Just One of the Girls with Corey Haim (1993) and reprised as She’s the Man with Amanda Bynes (2006). Photo: Columbia Pictures/Everett Collection

Hua Mulan (transcribed sixth century)Hua Mulan (literally wood-orchid flower) was a legendary heroine who disguised herself as a man to take her... Hua Mulan (transcribed sixth century)Hua Mulan (literally wood-orchid flower) was a legendary heroine who disguised herself as a man to take her father’s place in the army. Battling for over a decade, she refused all rewards except a swift mount to return home. Hua Mulan was given a Disney makeover as Fa Mulan in 1998. Photo: Buena Vista Pictures/Everett Collection

Lucky Cheng’s (opened 1993)Self-professed “drag queen capital of the world” and bachelorette party central, Lucky Cheng’s is moving on uptown af... Lucky Cheng’s (opened 1993)Self-professed “drag queen capital of the world” and bachelorette party central, Lucky Cheng’s is moving on uptown after nearly two decades in the East Village. The original location was previously a gay bathhouse and an ancient Roman theme restaurant. With its move to 52nd Street, the new Lucky’s demonstrates that drag — like Times Square — has cleaned up its act and become family friendly. Photo: Michel Setboun/Corbis

Tony Curtis and Jack Lemmon in Some Like It Hot (1959)Another dress up and ‘fess up romp, Some Like It Hot stars Tony Curtis as Joe/Josephine ... Tony Curtis and Jack Lemmon in Some Like It Hot (1959)Another dress up and ‘fess up romp, Some Like It Hot stars Tony Curtis as Joe/Josephine and Jack Lemmon as Jerry/Daphne. Struggling musicians in Prohibition Chicago, Joe and Jerry witness a gangland massacre and join an all-girl jazz band to escape the mob. Trading their tuxes for false lashes and falsies, the “ladies” set off for Florida. But once Joe falls for the band’s singer (Marilyn Monroe), he devises a third persona (Junior) and a third costume (ascot and captain’s hat) in order to woo her. Photo: Sunset Boulevard/Corbis

Murray Hill (debut 1996)Betsey Gallagher was a photography grad student at the School of Visual Arts when her M.F.A. thesis (a series of cross-d... Murray Hill (debut 1996)Betsey Gallagher was a photography grad student at the School of Visual Arts when her M.F.A. thesis (a series of cross-dressed portraits of herself as a mayoral candidate) gave birth to a write-in campaign and an alter ego. A pioneering drag king, Murray Hill is the self-proclaimed “hardest-working middle-aged man in show business.” A throwback to the Catskills comedians and the “emcee of choice” for the neo-burlesque scene, Hill hosts Dita Von Teese’s tour. Photo: Andrew H. Walker/Getty Images

Tim Curry in The Rocky Horror Picture Show (1975)Stranded on a rainy night, Brad and Janet stumble upon the castle of Dr. Frank-n-Furter, the “... Tim Curry in The Rocky Horror Picture Show (1975)Stranded on a rainy night, Brad and Janet stumble upon the castle of Dr. Frank-n-Furter, the “Sweet Transvestite from Transsexual Transylvania.” Somehow, Tim Curry manages to make the Dr.’s corset and pearls look positively virile and Frank-n-Furter has become the sex symbol of cinematic trannies. No surprise: He seduces both Brad and Janet before the night is through. Photo: 20thCentFox/Everett Collection

Ted Levine in The Silence of the Lambs (1991)Thomas Harris’sThe Silence of the Lambs and Jonathan Demme’s film adaptation exploit the cul... Ted Levine in The Silence of the Lambs (1991)Thomas Harris’sThe Silence of the Lambs and Jonathan Demme’s film adaptation exploit the cultural anxieties surrounding transvestites and transsexuals. Serial killer Buffalo Bill mistakenly believes he’s a transsexual. Gender clinics refuse him treatment, so he self-medicates with hormones, and murders women and flays their skins in order to sew “himself a girl suit out of real girls.” Photo: Orion Pictures/Everett Collection

Edward D. Wood Jr. in Glen or Glenda (1953)After Christine Jorgensen’s headline-making surgery in 1952, Ed Wood Jr. wrote, directed, and starre... Edward D. Wood Jr. in Glen or Glenda (1953)After Christine Jorgensen’s headline-making surgery in 1952, Ed Wood Jr. wrote, directed, and starred in Glen or Glenda. An enthusiastic cross-dresser himself, Wood’s film features a psychiatrist narrating the stories of Glen/Glenda, a closeted heterosexual transvestite, and Alan/Ann, a pseudo-hermaphrodite who identifies as a woman. Despite being described by Leonard Maltin as “possibly the worst movie ever made,” Glen or Glenda has become a cult classic. Its production is chronicled in Tim Burton’s Ed Wood. Photo: Everett Collection

Radclyffe Hall (1880–1943)Well-born lesbian Radclyffe Hall assumed her father’s name and favored short hair, bow ties, and smoking jackets. Borr... Radclyffe Hall (1880–1943)Well-born lesbian Radclyffe Hall assumed her father’s name and favored short hair, bow ties, and smoking jackets. Borrowing the terminology of sexologist Richard von Krafft-Ebing, Hall considered herself a “congenital invert” with a “masculine soul, heaving in the female bosom.” Her 1928 novel, The Well of Loneliness — which mirrors her own life — was deemed obscene and all copies were ordered destroyed. Photo: Bettmann/Corbis

André J. (b. 1979)Sometime party promoter, all-time fabulous André J. is post-trans and past gender. Proving that a beard goes gre... André J. (b. 1979)Sometime party promoter, all-time fabulous André J. is post-trans and past gender. Proving that a beard goes great with a gown, André doesn’t consider himself a cross-dresser. He does consider himself “an icon,” a “bodhisattva,” and a “muse.” His infectious positivity and free-to-be attitude helped him land the cover of French Vogue. Photo: Astrid Stawiarz/Getty Images

Julie Andrews in Victor Victoria (1982)Like Tootsie and Some Like It Hot, Victor Victoria centers on an out-of-work performer who cross-dresses... Julie Andrews in Victor Victoria (1982)Like Tootsie and Some Like It Hot, Victor Victoria centers on an out-of-work performer who cross-dresses to get a job. Only this time, Julie Andrews’s Victoria is a female impersonating a female impersonator. Unable to get straight work as a soprano, she pretends to be a man pretending to be a woman and becomes the toast of Paris. Andrews demonstrates that sometimes it takes tails and a cigar to be ladylike. Photo: MGM/Everett Collection

Virginia Woolf's Orlando (1928)Virginia Woolf called Orlando “an escapade, half-laughing, half serious.” Her time-traveling, gender-swapping pr... Virginia Woolf's Orlando (1928)Virginia Woolf called Orlando “an escapade, half-laughing, half serious.” Her time-traveling, gender-swapping protagonist, Orlando, begins the tale as an aristocratic lover of Elizabeth I and ends it, in 1928, a modern woman. Orlando’s transition is “accomplished painlessly and completely,” with a change of pronouns and a change of clothes. Sally Potter’s film adaptation is a virtual timeline of period dress, with Tilda Swinton wearing doublets and breeches, corsets and periwigs, motorcycling leathers, and trousers — all with equal aplomb. Photo: Mary Evans/Everett Collection

The co*ckettes (1969–1972)George Harris was an idealistic stage actor went he left New York for San Francisco in 1967. When he arrived, Harris re... The co*ckettes (1969–1972)George Harris was an idealistic stage actor went he left New York for San Francisco in 1967. When he arrived, Harris reinvented himself as a psychedelic glitter-bearded acid queen named Hibiscus. Along with like-minded “women, gay men, and babies,” Hibiscus founded a drug and drag troupe called the co*ckettes. Their bawdy, ecstatic musical revues — “Tinsel Tarts in a Hot Coma,” “Pearls Over Shanghai,” “Hollywood Babylon” — were declared “the only true theater” by Truman Capote. Photo: Bud Lee/The Serge Group

Cate Blanchett in I’m Not There (2007)Besides the opening caption — “Inspired by the music and the many lives of Bob Dylan” — Todd Haynes’s exp... Cate Blanchett in I’m Not There (2007)Besides the opening caption — “Inspired by the music and the many lives of Bob Dylan” — Todd Haynes’s experimental biopic doesn’t mention Dylan’s name. Instead, the singer-songwriter is refracted through Haynes’s character study and inhabited by six actors, including a 13-year-old African-American boy and Cate Blanchett. Rather than being about Dylan, the film feels like him. The six actors “are all Bob Dylan” — as the film’s poster attests — but ultimately it’s Dylan who’s “not there.” Photo: Weinstein Company/Everett Collection

Queen Christina of Sweden (1626–1689)Mistaken for a boy at birth, Christina of Sweden was given the education of a prince and was crowned “Girl ... Queen Christina of Sweden (1626–1689)Mistaken for a boy at birth, Christina of Sweden was given the education of a prince and was crowned “Girl King” at age 6 when her father was killed in battle. Christina refused to marry and abdicated the throne to convert to Catholicism. Escaping through Denmark, she disguised herself as a man and styled herself as Count Dohna to make her way to Rome. Photo: Bettmann/Corbis

Marc Jacobs (b. 1963)Marc Jacobs has a flair for womenswear — designing and wearing it. A longtime lover of kilts, Jacob donned a sheer lace shi... Marc Jacobs (b. 1963)Marc Jacobs has a flair for womenswear — designing and wearing it. A longtime lover of kilts, Jacob donned a sheer lace shirtdress (Comme des Garçons, fall 2012 menswear) over his white boxers for the 2012 Met Ball, a look Seth Meyers duplicated as host of the CFDA awards at the special request of Anna Wintour. Before that, a bearded “Mrs. Jacobs” posed for the cover of Industrie. Styled by Katie Grand in vintage Marc Jacobs from her own closet, all the clothes were rightfully labeled “model’s own.” Photo: Steve Eichner/WWD/CondÈ Nast/Corbis

Kalup Linzy (b. 1977)Video and performance artist Kalup Linzy was raised on Guiding Light. His aunts would encourage him to imitate their favori... Kalup Linzy (b. 1977)Video and performance artist Kalup Linzy was raised on Guiding Light. His aunts would encourage him to imitate their favorite characters and he grew up wanting to be onscreen. He’s finally getting a chance with his soap-opera-styled video art. In pieces like “Conversations wit de Churen III: Da Young and Da Mess,” and “As Da Art World Might Turn,” Linzy and company act out melodramatic scenes. They lip-synch to distorted prerecorded dialogue, while often playing multiple roles and dressing in drag. In 2010, Linzy’s daytime dream came true when James Franco helped him land a cameo on General Hospital. Photo: Jonathon Ziegler/PatrickMcMullan.com

George du Fresne in Ma Vie en Rose (1997)The 7-year-old character Ludovic Fabre knows he won’t be a boy forever. With all of the innocence and ... George du Fresne in Ma Vie en Rose (1997)The 7-year-old character Ludovic Fabre knows he won’t be a boy forever. With all of the innocence and certainty of a child, he announces: “I’m a boy now but one day I’ll be a girl.” Ludo’s parents struggle to understand, and things escalate when Ludo stages a wedding with the boy next door. By movie’s end, Ludo’s insistence has cost his father his job and forced the family to move, but the “boygirl’s” self-conviction remains unwavering. Photo: Bureau L.A. Collection/Sygma/Corbis

“Cindy Shermans” (2012)In conjunction with the Cindy Sherman retrospective at the SFMOMA, the San Francisco Bay Guardian asked local drag queens... “Cindy Shermans” (2012)In conjunction with the Cindy Sherman retrospective at the SFMOMA, the San Francisco Bay Guardian asked local drag queens to re-create four portraits from the artist’s “Untitled Series.” Lady Bear, Fauxnique, Lil Miss Hot Mess, and Boy Child made deft Sherman forgeries, adding a meta layer to Sherman’s uncanny self-portraiture. Photo: Keeney + Law

Kanye West (April 17, 2011)What’s that jacket, Margiela? Fashionphile Kanye West has rhymed about “dinner with Anna Wintour,” and “that new Phoe... Kanye West (April 17, 2011)What’s that jacket, Margiela? Fashionphile Kanye West has rhymed about “dinner with Anna Wintour,” and “that new Phoebe Philo,” and even presented the Céline designer with her CFDA award. But Kanye truly pledged his fashion allegiance when he wore Céline’s foulard-print silk blouse (spring 2011) to perform at Coachella. Paired with Balmain jeans, a Cartier bracelet, and Lanvin sneakers, Yeezy proved he’s not scared of buttoning on the left. Photo: Kevin Winter/Getty Images