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The tender gender-bender

Job description: Films about cross-dressing males are 10 a penny, and many is the director who has dressed up his hairy-chested, square-jawed leading man in a frock to elicit some cheap laughs.

When it comes to the tender sex, however, there's nothing intrinsically hilarious about seeing a woman dressed as a man. Films that feature female-to-male cross-dressing are generally more thoughtful fare, making powerful points about how difficult it is to be a woman in a man's world.

Recently seen in: Offside, Jafar Panahi's banned-in-Iran film about the travails of female soccer fans (right). Shot in a semi-documentary style, the film focuses on the Iranian football team's 2005 World Cup qualifier against Bahrain, and how some tenacious female fans resort to dressing as men, risking harsh punishment if exposed, for the love of the game. The film uses intelligent comedic touches to highlight the hypocrisy and absurdity of the Iranian regime.

Most likely to say: 'Of course my beard is real.'

Classics of the genre: Hilary Swank won an academy award for her role as Brandon, a transgender teenager who, although born female, yearns to be otherwise in Boys Don't Cry (1999). Once she's unmasked, lots of nasty repercussions follow in her redneck town.

A sophisticated twist on the genre is Sally Potter's Orlando (1992), an adaptation of the Virginia Woolf story about a nobleman at the court of Queen Elizabeth I who is commanded to stay forever young. Miraculously, he does just that, and the film follows him through several centuries and a sex change. Fed up with men, the androgynous Orlando morphs subtly into a female after a stint as an ambassador in Asia.

Even more of a mind- bender is Desperate Housewives' Felicity Huffman, who became possibly the first woman to play a man who's willing to undergo surgery to become a woman in Duncan Tucker's Transamerica (2005). And then there's Barbra Streisand, dragging up as a nice young Jewish boy in Yentl (1983).

Ultimate Avatar: American Gwyneth Paltrow, treading the boards with the rest of the cross-dressing thesps in Shakespeare in Love, for which she won a best actress Oscar in 1998.

Not to be confused with: Annie Lennox, Brigitte Neilsen.

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