Former welterweight champion Oscar de la Hoya is making headlines again for his penchant for cross-dressing. An Internet photo of the retired champ in fishnet stockings and high heels circulated years ago, but he claimed the picture was fake. From Miss Jay to Andrej Pejic, see photos of other famous cross-dressers.
Nicknamed "Queen of the Catwalk" by his friend and co-star Tyra Banks, the flamboyant runway coach and judge on America's Next Top Model entered the industry after the head of Elite Model Management spotted him dressed in drag at a club. Miss Jay (né Alexander Jenkins) first met Banks backstage at a runway show in New York. The two became fast friends when he gave her tips on strutting the runway. By the early '90s, he had a big following as a modeling coach, working with Naomi Campbell and Kimora Lee Simmons. On America's Next Top Model, Miss Jay's outfits are often as over-the-top as his personality. "I'm not a yes man," he said in an interview. "If people don't like it, I say, well, honey, I'm on TV looking outrageous—what do you expect?"
Before he became one of the most famous drag queens in the entertainment industry, RuPaul was a struggling actor and musician in Atlanta. It wasn't until he started dressing up as a woman, performing at clubs in the late '80s and early '90s, that he finally came into his own. In 1993, his hit single "Supermodel (You Better Work)" and music video catapulted him to stardom. Since then, he's lived by the motto "You can call me he. You can call me she. You can call me Regis and Kathie Lee; I don't care! Just as long as you call me." Two years later, The RuPaul Show debuted on VH1, with the drag queen interviewing celebrities like Mary J. Blige and Cyndi Lauper. He's currently searching for America's next drag superstar as host of a VH1 reality show, RuPaul's Drag Race.
With bone structure like Cindy Crawford and a body like Kate Moss, it's difficult to tell that the model for Marc Jacobs's spring 2011 advertising campaign is actually a man. Andrej Pejic, 19, started his career in 2009 and quickly became a transgender modeling sensation. Having debuted in Jean-Paul Gaultier's Paris show last year, he has since appeared in major magazines and walked the runway at men's shows in Paris.
In the 1993 comedy Mrs. Doubtfire, Robin Williams dons a wig, a facemask, and granny shoes in order to pass as an elderly British nanny to see his kids after being kicked out of his house. He plays the role so well that his wife and kids are shocked when, months later, Mrs. Doubtfire finally reveals his true identity.
Dustin Hoffman plays a talented but difficult actor who can land a part only when he pretends to be "Dorothy Michaels." Of course, having to keep up a new gender among cast members and significant others is tougher than he thinks. To prepare for the role, Hoffman watched the classic drag movie La Cage aux Folles multiple times.
In a desperate attempt to play soccer after her team is cut, Amanda Bynes dons a short wig and baggy jeans in a (fairly unconvincing) attempt to pass as her brother and join his school's soccer team in the 2006 comedy She's the Man. Lured by the muscular charms of her fellow teammate, Channing Tatum, she finally exposes herself (literally) to the school, wins the game—and snags Tatum.
During his 15-year reign, starting in 1574, King Henri III of France insisted on being called "her majesty" while donning drag in the courts. His clothes were noted as flamboyant even for the extravagant French style of the time. Historians have wondered if he was gay or bisexual; he often took mistresses.
What started as comedian Barry Humphries's satirical play on an Australian housewife in 1955 slowly evolved into Dame Edna, a purple-haired, cat-eye-glasses-wearing firebrand. Criticizing everything from Thatcher-era policies to William and Kate's wedding, Humphries's alter ego continues to be an ironic look at mainstream culture on late-night shows and Broadway stages. She's even written several books including My Gorgeous Life, an autobiography.
In the 1959 Marilyn Monroe film Some Like It Hot, Tony Curtis and Jack Lemmon go undercover in an all-girl band after accidentally witnessing a mob massacre. Naturally, the girls suspect nothing strange about their two unusually masculine new members, even though the film had to be changed from color to black and white to subdue their heavy makeup.
Courtesy Everett Collection
