12 Famous Ladies Who Absolutely LOVE To Cross-Dress

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Famous Ladies Who Love To Cross-Dress

You do YOU, ladies.

Lady Gaga's unshakable act as "Jo Calderone" throughout the MTV Video Music Awards left many scratching their heads. But she's not the first famous female to dip her foot into cross-dressing.

From Cate Blanchett's performance as Bob Dylan in I'm Not There, to Katy Perry's transformation into a rock legend, see these leading ladies dressed as gentlemen.

1. Lady Gaga

Though she's known for making statements in monstrously high heels and horny shoulders, fashion icon Lady Gaga went a different route when she opened the 2011 MTV Video Music Awards in a cuffed white t-shirt and sideburns.

Gaga channeled her alter ego Jo Calderone to open the show and didn't sway from her male persona — a combination of Grease's Danny Zuko and The Outsiders' Two-Bit Matthews — throughout her performance and the entire award ceremony. There were even reports that she used the men's bathroom at the Los Angeles auditorium and wore a prosthetic penis.


2. Cate Blanchett

In the 2007 Bob Dylan biopic I'm Not There, Cate Blanchett was cast to play Jude Quinn, who represented a Dylan from 1965 to 1966. Critics and audiences were largely impressed. Blanchett was nominated for a Screen Actors Guild Award and an Academy Award, and won a Golden Globe for her performance.

"Casting a woman in this role reveals a dimension to the acerbic Dylan of this era that has rarely been noted," critic Anthony DeCurtis wrote in The Chronicle of Higher Education. "Even as she perfectly mimics every jitter, sneer, and caustic put-down, Blanchett's translucent skin, delicate fingers, slight build, and pleading eyes all suggest the previously invisible vulnerability and fear that fueled Dylan's lacerating anger. It's hard to imagine that any male actor, or any less-gifted female actor for that matter, could have lent such rich texture to the role."

​3. Katy Perry

In 2008, for Katy Perry's 24th birthday, the pop star decided to celebrate by dressing up as the late lead singer of Queen, Freddie Mercury, mustache and all.

"Freddie Mercury was — and remains — my biggest influence," Perry said. "The combination of his sarcastic approach to writing lyrics and his 'I don't give a f*ck' attitude really inspired my music."

Even Mercury's co-founder (and Queen songwriter) Brian May bought the comparison. Upon meeting Perry in 2009, he blogged, "She writes highly original songs, she plays great guitar, and sings beautifully, effortlessly accurately and from the heart. But the best thing of all is her command of mood, which makes me think of Freddie."

4. Annie Lennox

Lady Gaga's VMA act  had some claiming plagiarism, since it looked oddly similar to Annie Lennox's appearance at the 1984 Grammy Awards. When the Eurythmics front-woman took to the stage to perform "Sweet Dreams (Are Made of This)," she looked like an Elvis impersonator, complete with greased hair and an equally shiny ensemble.

"There had been quite a controversy about my gender, and so just to really push the envelope I took it on myself to shake them up a bit," Lennox later told People about her drag show. "I got a man's suit and I had makeup stubble. When I got to the stage to perform, the stage manager was totally freaked out because he couldn't see me. He didn't realize who I was. When the curtain came up, you could almost hear the audience inhale."


5. Mariah Carey

She may be the definition of femininity, but songstress Mariah Carey grew a pair and a goatee for her music video "Obsessed." Though it was reported that Carey was posing as Eminem, who mocked her on his track "Bagpipes From Baghdad," to play the obsessed man in the video, she shot down the rumors.

"When I look at that stalker and me with the beard and the whole nine yards, I look like my cousin Chris," she told MTV News. "Basically, you know, all the speculation about who I'm playing in the video, it's not accurate."

6. Katharine Hepburn

For her first on-screen role opposite Cary Grant, Katharine Hepburn was, interestingly enough, playing a male. Hepburn plays the title character in 1935's Sylvia Scarlett, a female con artist masquerading as a boy to escape the police with her embezzling father.

Thanks to the removal of her braids, the swapping of the name on her luggage tag from Sylvia to Sylvester, and a lot of effort from makeup artist Mel Berns, the beautiful Hepburn makes an impressive transformation, even though the movie was a flop.

"The dynamic Miss Hepburn is the handsomest boy of the season," wrote Richard Watts, Jr. of The New York Herald Tribune.

7. Drew Barrymore and Cameron Diaz

As private investigators in the 2000 reboot of Charlie's Angels, Drew Barrymore, Cameron Diaz, and Lucy Liu took on many disguises, from yodeling telegram deliverers to members of a drag-race pit crew. But Barrymore and Diaz took the drag idea to a new level in order to break into a high-security building to recover some allegedly stolen, revolutionary voice-recognition software.

Sporting some facial hair and wigs, the two actresses managed to pass as businessmen. "Drew dressed up as Harry Potter to go undercover," director McG joked to USA Today.

8. Barbra Streisand

As the title character, a Jewish girl living in Poland in the early 1900s, Barbra Streisand's performance in 1983's Yentl had her transforming into a 17-year-old boy and winning over critics in the process. In order to study in her community — an activity forbidden for women — Yentl decides to chop off her long hair, don some baggy pants, and affix a yarmulke in order to pass as a male student at a yeshiva.

"Miss Streisand makes a wonderful boy, pert and quick-witted, and her masquerade is by no means unconvincing," The New York Times reviewed, despite the fact that she was also a 40-something playing a teenager. "She brings a disarming humility to her performance as Anshel (the male name she adopts), not afraid to appear unglamorous or to be upstaged by a pretty co-star."

9. Amanda Bynes

In a far less serious approach to the gender struggle storyline, the comedy She's the Man based its plot on Shakespeare's Twelfth Night. The film stars Amanda Bynes as a tomboyish high-schooler named Viola Hastings, who disguises herself as her twin brother in order to play with the boys' soccer team after the misogynistic coach refuses to let her play because she's a girl.

"The cast watched different movies every night to help inspire us: Twelfth Night, Mrs. Doubtfire, Tootsie, White Chicks, and I went to see Transamerica," Bynes told People of her cross-dressing cinematic education. "They took a photo of Jesse McCartney and a photo of me, and morphed us and I looked like a legitimate guy."

10. Linda Hunt

Peter Weir's 1982 film The Year of Living Dangerously starred Mel Gibson and Sigourney Weaver as two news correspondents in Indonesia on the eve of the attempted coup to overthrow President Sukarno in 1965. Linda Hunt was cast as Billy Kwan, Gibson's character's local photographer contact, and she blew critics away.

"Billy Kwan is played, astonishingly, by a woman — Linda Hunt, a New York stage actress who enters the role so fully that it never occurs to us that she is not a man," Roger Ebert reviewed. "This is what great acting is: a magical transformation of one person into another."

The performance earned Hunt an Academy Award for best supporting actress, marking the first time in Oscar history that an actor won an award for playing a character of the opposite sex.

11. Julie Andrews

Victoria Grant, played by Andrews, is a struggling soprano in 1930s Paris at the start of another 1982 Oscar favorite, Victor Victoria. Things eventually turn around when Victoria auditions for a gig as a female impersonator, taking on the persona of a man named Count Victor Grazinski who pretends to be a woman.

"When I did the film, I asked lots of questions of my leading men, James Garner and Robert Preston, and I watched them very closely, and they were very helpful," Andrews told Dance magazine. "I came to the conclusion that if I adopted a real stillness as a man, I would probably have a better chance of being believable."

12. Mulan

In true Disney-princess fashion, 1998's animated movie Mulan follows the story of a suffering daughter who wants the exact opposite of what her parents wants from her. In this installment, Mulan is the only daughter of elderly warrior Fa Zhou, who's the only male in their family. When he's drafted into the army, Mulan decides to impersonate a man, calling herself Ping, and takes his place in the war to counter a fictitious Hun invasion.

​"The movie's point is to show that Mulan is as valuable as any boy," Time magazine noted in the wake of the film's release. Mulan's producer Pam Coates added, "You see Mulan get physically stronger, but she also uses her brain. We tried really hard to balance her feminine and masculine side."

This article was originally published at The Daily Beast. Reprinted with permission from the author.


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