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Darling Or Drag? Cinema’s Best And Worst Cross-dressers

Cross-dressing has been a part of drama for as long as I can remember. Granted I’m not that old, but even in Shakespeare’s day cross-dressing could be found. Not just the fact that females had to be played by males, but even the characters themselves would cross-dress; most notably Viola from Twelfth Night. So I guess when that was first performed they had a boy, playing a girl, pretending to be a boy.

Sometimes cross-dressing is used to great comedic effect, and sometimes it is the catalyst for moving and controversial drama. And of course, there are the times when it is used to scare the living knickers off you.

ALBERT NOBBS (Glenn Close) takes the dramatic approach and sees a woman who has passed as a man for the majority of her working life, as women are discouraged from being independent. To celebrate its release on DVD we take a look back at cinema’s most memorable cross-dressers and we ask are they ‘Darling’ or just a ‘Drag’.

Dil – THE CRYING GAME (1992)                                                                                                                                                      

Dil (Jaye Davidson) knows all there is to know about the crying game. Not surprising since she is getting over the death of her boyfriend, a British soldier who was kidnapped by IRA terrorists. Luckily Fergus (Stephen Rea) soon comes into her life. Dil works as a hairdresser where she’s a dab hand with a pair of scissors.  When she’s not practicing her beauty techniques she’s belting out classic tunes from the 1960s.

Darling or Drag? Considering the character of Fergus has no idea that Dil is a man, and neither did the majority of the audience at the time, we’re going to have to say Dil is a Darling. Luckily actor Jaye Davidson had such a unisex name, had he been called David, Tyrone, or Mario then the whole cover would have been blown.

Michael Dorsey – TOOTSIE (1982)

What to do when you’re such a dick that no one will hire you as an actor anymore. Simple, turn your life into an act by developing a brand new persona. That’s what Michael Dorsey (Dustin Hoffman) does, donning a dress and becoming Dorothy Michaels (no points for originality). Dorothy becomes a huge television star, which creates problems when the woman he beat for the part on the show falls in love with him as Michael, and he falls in love with a co-star but she only knows him as Dorothy. My head hurts!

Darling or Drag? He does manage to convince a nation that he is a she. The voice, clothes and mannerisms all work in his favour, making this a Darling.

Mulan – MULAN (1998)

To prevent her father from having to go to war, Mulan (Ming-Na) convinces government officials that she is a son rather than a daughter. Off to battle the Huns she goes with guidance on how to walk and talk like a man. There’s some brave if subtle handling of homosexual subtext for a Disney film. It’s kind of like THE CRYING GAME for kids.

Darling or drag? Becomes the greatest Chinese warrior EVER! And doesn’t cry over a broken nail once. Women have come a long way since Eve. Congrats Mulan, you’re certainly Darling.

Daniel Hillard – MRS DOUBTFIRE (1993)

After Daniel Hillard (Robin Williams) is no longer allowed to see his children he does what any sane man would do: he dresses up as an elderly Scottish woman and applies to be the children’s nanny. This allows him to spend time with his kids, even if it is all a bit creepy. There seems to be a number of films in which men decide the best way to tackle their problems is to dress up like a woman. Beats the hell out of becoming a better person I suppose.

Darling or Drag? I will forever be haunted by that image of Robin Williams dressed as a woman and standing up to take a piss. Talk about not staying in character. It’s a Drag.

Malcolm Turner – BIG MOMMA’S HOUSE (2000)

Malcolm Turner (Martin Lawrence) has to go undercover as a big fat woman. Can you see where the humour is going to come from? This is different to the others on this list, as he is trying to pass as an actual person and isn’t making up his own character. Luckily for him everyone seems to be completely stupid, because he looks, sounds, and acts nothing like her.

Darling or drag? It’s hard to imagine how anyone could be fooled by Martin Lawrence’s turn as a woman. Like TOOTSIE, he also falls for a woman when dressed as a woman, but it just feels wrong. This is a Drag.

Jame Gumb – SILENCE OF THE LAMBS (1991)

Jame Gumb (Ted Levine) keeps himself to himself but stays busy with his hobbies, such as caring for moths and sewing. And he likes nothing more than dancing to Q Lazzarus and tucking his member between his legs. He can sometimes be a bit dependent, especially when moving heavy furniture and he does seem to have an unhealthy attachment to his dog.

Darling or Drag? The whole killing in order to peel the flesh off women so he can construct a human skin suit takes cross dressing to a whole new level, and it’s one we can’t look favourably on. We try to be open minded, but there’s a limit. He’s a definite Drag.

Dr. Frank N Furter – THE ROCKY HORROR PICTURE SHOW (1975)

He’s just a sweet Transvestite from Transsexual Transylvania. Dr. Frank N Furter (Tim Curry) lives a hedonistic lifestyle with sex, parties, and rock ‘n’ roll. All while dressed in his fabulous fishnets. Furter isn’t one to let gender get in the way of a goodtime.  A wild boy with a PhD? He can make you a man in just seven days or even rose tint your world.

Darling or Drag? As mentioned before, he has a PhD, a wonderful singing voice, and knows how to have a good time. He does the unimaginable by dressing up in ladies garments but retaining his masculinity. He’s a Darling in our books.

Norman Bates – PSYCHO (1960)

When not playing dress up in his mother’s Sunday best, or dealing with the day to day running of The Bates Motel (try the leek and potato soup) Norman (Anthony Perkins) likes a bit of taxidermy. Master Bates was always very close to his mother, maybe a bit too close, and as such when he feels ‘little Norm’ perk up he gets a bit stab happy.

Darling or Drag? I’m afraid this one is a complete drag. Norman is by all accounts a very handsome man, so why he dresses up like some controlling haggard crone is beyond us. He’s not convincing as a woman and wouldn’t make a funny drag act either.

Joe and Jerry – SOME LIKE IT HOT (1959)

If you’re a musician on the run after witnessing a mafia execution ,and the only band hiring is of the all girl variety, what are you going to do? You get the best of both worlds with a great disguise and you can make some money at the same time. Once again though, those men just can’t help but fall for women that believe they are women. At least Joe has the sense to make up a third personality for himself as he tries to woo Sugar Kane (Marilyn Monroe), giving a hilariously bad Cary Grant impression.

Darling or Drag? They are both very convincing as ladies, and Jerry (Jack Lemmon) even manages to get a marriage proposal from a wealthy suitor. These two are a couple of Darlings.

 ALBERT NOBBS is released on DVD 3rd September and you can pre-order it here.

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Luke likes many things, films and penguins being among them. He's loved films since the age of 9, when STARGATE and BATMAN FOREVER changed the landscape of modern cinema as we know it. His love of film extends to all aspects of his life, with trips abroad being planned around film locations and only buying products featured in Will Smith movies. His favourite films include SEVEN SAMURAI, PASSION OF JOAN OF ARC, IN BRUGES, LONE STAR, GODZILLA, and a thousand others.

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