#10 – Mulan

Aha, see… even Disney are down with a bit of gender bending. Welcome to Mulan, the tale of a young girl who impersonates a man so that she can take her father’s place in the army. Or so she claims, anyway. Is this really for the sake of your father Mulan, or are you unhappy inside your female skin? This song pretty much clears things up…

“When will my reflection show who I am inside?” Simple enough; plus we have the handy pointer of her wiping away half of her make-up and partially revealing Mulan in her (later seen) male persona. Either way, she heads off to war and falls in love with Chang, her captain, which causes a few awkward faux-homo moments. She also enjoys a montage of soldierly activities, all played out to the dulcet tones of Donny Osmond promising her that he WILL “make a man out of you”. Mulan is far happier in her male guise, right? And, weirdly, nobody ever catches on, even when she bathes in a nearby lake with some of her new friends. In a lake. Water IS transparent, right?

 

#9 – Victor Victoria

By jove, is that Julie Andrews? DRESSED AS A MAN? Yes, yes it is. So what? We can’t expect her to spend her entire acting career skipping across the Alps with a gaggle of children or sailing through the sky with a magic umbrella now, can we? This is her effortless performance in the wonderfully witty Victor Victoria. Andrews is a female soprano, struggling to make ends meet. On the advice of her gay friend, she finds work playing a male female impersonator; she’s a she pretending to be a he who pretends to be a she. Complex, huh? No wonder it completely messes up her personal life! A very daring storyline for the 80s (weird, considering it was the decade of Boy George!), this film is still as fresh and funny as it was when it first hit the silver screen.

 

#8 – Mrs Doubtfire

Robin Williams is an utter comic genius in the majority of his movies, but this one really takes the biscuit. Not only are we treated to a vast collection of Williams’ best accents and personas, but we are also treated to him dressing up an older lady in order to spend time with his children. Why? It’s all pretty much down to a nasty divorce and a messy case of unemployment; taking on the task of becoming his children’s new nanny sorta kills two birds with one stone there. He gets a pretty packet of cash to pocket AND some one-on-one time with the kids. What could go wrong? Well, quite a lot actually.

 

#7 – Yentl

Goodness, can you imagine the outcry if I hadn’t included Barbra Streisand’s performance in Yentl? So yeah, that’s Streisand up there, in her role of a young Jewish girl who impersonates a young Jewish boy, in order to enter religious training. The glasses are a particularly nice touch, I feel. The message is simple; anything is possible. Especially if you dress up as a man. Plus we get an absolutely formidable soundtrack, filled with the kind of showstopping tunes that Andrew Lloyd Webber is desperate to get his hands on! Just timeless.

 

#6 – The Birdcage

That’s right, I managed to include not just one but TWO Robin Williams movies in this countdown. Only this one is by far superior and not just because it co-stars Nathan Lane as Williams’ drag queen lover. And Christine Baranski, as his one-time heterosexual fling. And Hank Azaria, as an extremely camp illegal immigrant in a thong. The film follows two gay lovers welcoming “their” son home for the weekend, whereupon he informs them that he’s engaged. Only he’s not just engaged to a nice, normal girl; in fact, he’s engaged to the daughter of Senator Kevin Keeley, one of THE most right-wing moralists of the USA. The solution is obvious. Check it out:

It’s the great chemistry between all of the actors in this which makes it such a believable movie, despite the OTT concept. And, sure, it’s completely and pant-wettingly hilarious, but it also has a strong moral message. One which challenges our prejudices and urges us towards acceptance. “Yes, I wear foundation. Yes, I live with a man. Yes, I’m a middle-aged fag. But I know who I am.” You just can’t beat a script like that – completely wonderful. Watch it, laugh at it, fall in love with it and, just maybe, be inspired by it.

 

#5 – The Silence Of The Lambs

Did anybody want a dose of terror with their cross-dressing movie? If so, you definitely can’t go wrong with The Silence Of The Lambs. Cue Ted Levine as Buffalo Bill, a cross-dresser suffering from extreme paranoid delusions and murdering size 14 women. Why? So he can skin them, of course! Yup, Bill’s taking the female impersonation to an entirely new level by wearing the neatly sewn-together skins of his female victims. Which, unsurprisingly, earned the movie a backlash from gay and transgender campaigners. However, it does lend an interesting dimension to his character and an extra wave of terror to proceedings. Pretty much The Godfather of the thriller genre.

 

#4 – Tootsie

Dustin Hoffman. That’s all most people need to hear in order to convince them to see any of his movies. And yet, somehow, I have a feeling that won’t quite cut the mustard this time, so do you want an even better reason to watch it? Bill Murray. Bill Murray, Bill Murray, BILL MURRAY.

Dustin Hoffman plays an actor down on his luck (that’s the cue for the mournful wail of a violin to start up!). The only job opening in sight is for a woman in a daytime drama, which he goes for, dressed up as Dorothy Michaels. He lands the job, inspires women everywhere and gets caught up in a sitcky love triangle between his female co-star and her father. It’s not a serious film; in fact, it would be foolish to deny that this is a comedy. Which makes it okay for Dustin Hoffman’s female impersonation to be about as suspicious as a puppy standing next to a steaming turd.

 

#3 – Boys Don’t Cry

Of course, it goes without saying that Hilary Swank’s performance in Boys Don’t Cry is probably THE stand-out role of her career so far. She’s Brandon Teena, the popular new boy in a small American town. He’s in with the boys, he’s dating the local beauty queen and basically has a charmed life. Until they all find out that he was born a girl under the name of Teena Brandon… and then his life is completely ripped apart. Tragic and theatrical, this movie doesn’t shy away from the sordid details of Brandon’s life, yet still manages to make him a character we sympathise with completely. Which means that this gritty flick is pretty harrowing at times, but a very rewarding watch. Must-see stuff.

 

#2 – Priscilla, Queen Of The Desert

This is, quite definitely, one of those films that you have to see before you die. And it’s all so deceptively flippant; two drag queens and a transsexual get a cabaret gig in the middle of the Australian desert. Instead of bagging seats on the nearest plane, the catty trio decide to drive there inside a lavender bus, which leads them into all sorts of trouble; from a bloody hate-fuelled beating to a rendition of Gloria Gaynor’s I Will Survive to an aborigine audience, this film is filled to the brim with surprises. And wigs. Let’s not forget the wigs. The script is fantastic, delving equally into an endless barrel of hilarious scenarios, as well as the gritty realities of life for transgendered individuals. The cast is absolutely stellar; who’d have guessed that Hollywood giants Terence Stamp, Guy Pearce and Hugo Weaving would be so good at dancing in high heels? Plus, despite some tearjerking scenes,the whole viewing experience is an utterly joyful one – you’ll never forget what the Thai bride does to that ping pong ball.

 

#1 – The Rocky Horror Show

Ohhhhh my. Is it just me, or does Tim Curry look ridiculously hot in his Frank N Furter get up? Obviously, I don’t mind if it IS just me, because that way there’s more to go around. How could The Rocky Horror Show NOT be my number one cross-dressing movie? It’s absolutely fantastic. Want proof? How about a little clip to whet your appetite:

Now how can you tell me that staring into Tim Curry’s heavily made-up eyes doesn’t make you weak at the knees? But you probably need a better reason for this making it to the number one slot, right? Hmm. How about the fact that it is THE cult movie of our lifetimes? It deftly and wittily rips apart the classic horror formula, throws in some fantastic music and a wealth of amazing stars. Susan Sarandon, anyone? Meat Loaf? TIM MOTHER-F*CKING CURRY? Ahem. I appear to have given myself over to absolute pleasure, so my apologies for that. Spare a thought for wholesome couple Brad and Janet, who have accidentally stumbled across a nest of transvestite aliens from an obscure planet known only as “sweet transsexual Transylvania”. And, hidden deep within the castle, awaits the charismatic and violent Frank N Furter, whom intends to unveil his latest creation to them all, at any cost… This deliciously out-there film is still as popular as it ever was in the 70s, showcasing beauty and horror and lust in oh so very many different ways. So thrill me, chill me, fulfill me and give me The Rocky Horror Show over all those other films any day. “So come up to the lab and see what’s on the slab. I see you shiver with antici… pation.” It’s going to be abso-bloody-lutely amazing.

 

But I don’t profess to have the last word on all things transgender… what’s YOUR favourite cross-dressing movie of all time?