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Cross Dressing: The Pictorial

Some Like It Hot (1959)

Joe/Josephine (Tony Curtis) and Jerry/Daphne (Jack Lemmon)–the girls next door. As musicians on the run from the mob, Joe and Jerry dress up and hide out with an all-girl band, all the while lusting after Sugar Kane (Marilyn Monroe), one of the players. But honestly. Try and name another man who looked as good in a dress and make-up than Joe. Just look at those eyes, those full lips. Standing next to the goofy and clownish Jerry, however, anyone would look good.

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Rocky Horror Picture Show (1975)

Dr. Frank-N-Furter (Tim Curry)–the quintessential drama queen. Strutting and primping, Dr. Frank wears a leather teddy and fishnet stockings like no one else can. Just look at the detailed eye make-up and the gloves, which are a nice touch. Convincing his uninvited houseguests to stay, he is all at once menacing yet strangely sexy, as he belts out the benefits on being a transvestite from Transylvania.

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Tootsie (1982)

Michael/Dorothy Michaels (Dustin Hoffman)–the independent woman. Unassuming, out-of-work actor Michael decides to don women’s clothing to get a soap opera role, and he is transformed into Dorothy, a tough-as-nails woman who knows who she is and what she wants. Dorothy may have to wear heavy make-up to cover up the stubble, but she’s got a style all her own. Just make sure the camera doesn’t get too close.

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Victor/Victoria (1982)

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Victor/Victoria (Julie Andrews)–the perfect gentleman. When down-on-her-luck Victoria takes on the persona of Victor, a male cabaret singer who dresses as a woman and shocks everyone by revealing she’s a man at the end of the show, he becomes the toast of the town. But Victor is–gasp–actually a woman. It’s all very confusing. However, Victor has class and style befitting an aristocrat–and remains the perfect gentleman, even while falling in love with macho mob guy, King Marchand (James Garner).

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Mrs. Doubtfire (1993)

Daniel/Mrs. Doubtfire (Robin Williams)–the doting grandmother. All divorced dad Daniel wants to do is be with his kids but his ex-wife (Sally Field) has other plans. Yet in order to make this happen, he dreams up Iphegenia Doubtfire, an older and much wiser woman, and is hired as the kids’ nanny. A cross between Mary Poppins and linebacker Lawrence Taylor, Mrs. Doubtfire cares little for her appearance, rarely shaving her legs, but manages to help Daniel learn more about being a dad then he thought he could.

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To Wong Foo, Thanks for Everything, Julie Newmar (1995)

Vida (Patrick Swayze), Chi-Chi (John Leguizamo) and Noxeema (Wesley Snipes)–the glamour queens. Taking their act on the road in a Cadillac convertible, these three gals decide to show middle America a thing or two about dressing for success. Vida is the sophisticated one, Chi-Chi the prissy and Noxeema the most flamboyant, all while their Dynel dresses flap in the breeze. When they decide to pour it on, bewildered onlookers better watch out.

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The Birdcage (1996)

Albert/Starina (Nathan Lane)–the consummate performer. The star of the hottest drag show in Miami, Albert a.k.a. Starina suffers mightily for his art. He cries, gnashes his teeth and generally considers himself a hack, while his significant other, Armand (Robin Williams), very patiently talks him through it Still, Starina always looks fabulous, sporting a mature and very glamorous look. Taking on the role as his son’s mother for the kid’s unsuspecting, soon-to-be in-laws, Albert positively shines.

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Boys Don’t Cry (1999)

Brandon Teena (Hilary Swank)–the troubled youth. When Brandon shows up in a small town in Nebraska with that Gap look–cropped hair, jeans and a plaid shirt–he immediately makes friends with some of the locals. Brandon even starts a fling with Lana (Chloe Sevigny), unbeknownst to her boyfriend John (Peter Sarsgaard), which spells trouble for the teenaged Brandon. It’s not easy being a boy in this town, especially when you are not exactly what you seem.

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Hedwig and the Angry Inch (2001)

The story centers on a songwriter named Hedwig, formerly Hansel, a transsexual whose operation is botched, leaving her with the titular “inch.” This musical extravaganza is based on writer/director/star John Cameron Mitchell‘s critically acclaimed off-Broadway play of the same name. Hedwig goes after her lover who has stolen her songs and has become a huge rock star, shadowing the ex-paramour’s tour with her own band, the Angry Inch, playing in diners and laundromats. During the course of this journey, Hedwig’s life story unfolds. One could say Hedwig is the not-so-proverbial woman scorned.

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