Katharine Hepburn in 'Sylvia Scarlett'
Hepburn plays the title character, a con artist who masquerades as a boy to stay one step ahead of the cops in this cross-dressing comedy from 1935. Believe it or not, the joke at the time was that Kate looked better as a boy. This was years before the pioneer of androgynous style became the iconic strong, modern woman.
Julie Andrews in 'Victor/Victoria'
Julie Andrews plays Victoria Grant, a straight woman impersonating a gay man who's a female impersonator in this 1982 musical-comedy. James Garner plays a macho straight guy who falls in love with the woman behind the man behind the woman. But all this needs to be sorted out. It doesn't help that the macho man has a gay bodyguard who pretends to be straight until he sees his boss in bed with—oh, never mind.
Cate Blanchett in 'I'm Not There'
In this loopy Bob Dylan biopic from 2007, the storied musician is played by six different actors, including Blanchett as the avatar for Dylan's shocking decision to go electric. Though some critics blasted the movie's unconventional structure, Blanchett shines as the defiant folk singer turned rocker. Director Todd Haynes reportedly chose a woman to play that phase of Dylan's career for its sheer, surprising otherness.
Marlene Dietrich in 'Morocco'
Before Madonna and Britney Spears even thought to be born, there was Marlene as Amy Jolly, in full tux and top hat, wreathed in smoke, kissing a girl after performing "Give Me the Man Who Does Things" in French. This was Dietrich's first scene in her first American movie (in pre-Code 1930), and the classy androgynous getup became her signature look.
Gwyneth Paltrow in 'Shakespeare in Love'
In this 1998 rom-com, Paltrow is Lady Viola, the muse who shakes William Shakespeare (Joseph Fiennes) out of his creative block to write "Romeo and Juliet." That Viola gets close to her crush by masquerading as a boy to win the role of Romeo in the play's embryonic form ("Romeo and Ethel, The Pirate's Daughter") isn't much of a stretch: Back in the day, it was taboo for a woman to be on stage, or even to love the theater.
Glenn Close in 'Albert Nobbs'
Close is the producer as well as the star of this 2011 film, about a woman who disguised herself as a man in 19th-century Dublin. The story is pretty bleak: Albert Nobbs lives imprisoned in the starched uniform of a hotel butler in a society that permits even less freedom for women, all for the dream of saving enough money to open a tobacco shop.
Jeanne Moreau in 'Jules and Jim'
Francois Truffaut's 1962 New Wave classic focuses on a love triangle involving Jules (Oskar Werner), Jim (Henri Serre) and Catherine (Jeanne Moreau), the woman they both love. Exuberant and playful, Moreau runs away with the movie—particularly when she dresses as a man and races her two lovers across a bridge, in one of the most famous tracking shots ever.
Linda Hunt in 'The Year of Living Dangerously'
Diminutive, gravelly voiced Linda Hunt won an Oscar for playing Billy Kwan, a biracial male dwarf who befriends a journalist (Mel Gibson) in Jakarta during the overthrow of its president. To audition for the role, Hunt wore a hairpiece and a fake mustache. When the 1982 film went into production, she cut her hair short, dyed it black, shaved her eyebrows and wore padding around her midsection to disguise her female form.
Barbra Streisand in 'Yentl'
To fulfill her dream of becoming a Talmudic scholar, Yentl Mendel (Streisand) adopts the dress and manner of a man and the name of her brother Anshel. At a yeshiva, she falls for her study partner, Avigdor (Mandy Patinkin), only to draw romantic interest from Hadass (Amy Irving), who is Avigdor's ex-fiancée (don't ask). Isaac Bashevis Singer, who wrote the story on which the 1983 movie is based, hated the adaptation.
Gloria Swanson in 'Sunset Blvd.'
Billy Wilder's 1950 look at the price of Hollywood fame includes a scene in which faded star Norma Desmond (Gloria Swanson) impersonates Charlie Chaplin—complete with bowler, spinning cane and crooked mustache—for struggling screenwriter Joe Gillis (William Holden). Lighthearted on the surface, the brief Chaplin bit entombs Norma in the silent-film era, and that of course is the reason she has been forgotten.
Salma Hayek in 'Frida'
Salma Hayek stars as Frida Kahlo in this 2002 biopic, dancing the tango with a woman (the Mexican painter was openly bisexual) and showing up for her sister's wedding photo dressed as a man. In one memorable scene, following a separation from fellow artist Diego Rivera, she is shown in a gray suit, drinking straight from a bottle, then slashing off her hair with scissors.
Hilary Swank in 'Boys Don't Cry'
Swank won an Oscar for dramatizing the life and hate-murder of trans man Brandon Teena, bringing attention to an issue that is now emerging in the mainstream. Her commitment to the 1999 role was so strong that the actress lived as a man for over a month before filming began—bound breasts, rolled-up socks in her pants and all—and refused to let the cast see her out of costume.
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