Edna Turnblad - Hairspray (2007)
Whether you prefer the bright colours and big ole smiles of the 2007 remake, or John Waters’s slightly darker original, there’s no denying that Hairspray is carried by the part of ‘larger-than-life’ teen star Tracy Turnblad’s mother, traditionally played by a man in full drag regalia.
Divine originated the role, but John Travolta definitely put his smooth dance moves to good use when he shimmied his way through the remake, and now everyone from Harvey Fierstein to our own Phill Jupitus have squeezed into the Turnblad fat suit.
Ed Wood - Ed Wood (1994)
"Get me transvestites, I need transvestites!" He may have been a terrible film director, but he had great taste in angora sweaters and pencil skirts.
Johnny Depp is on fine form as the cross-dressing film-maker.
Ned Kynaston - Stage Beauty (2004)
Richard Eyre’s romantic period drama is has been likened to ‘a fancy-dress version of A Star Is Born ’ (A.O. Scott, The New York Times), but Billy Crudup’s turn as Ned Kynaston, a confused actor famed for his portrayal of female characters, is full of subtle moments of brilliance.
Dr. Alex Hesse - Junior (1994)
If it wasn’t weird enough to have a movie where man-Hulk Arnie Schwarzenegger goes all Virgin Mary and ends up with child, things crank up a notch when he goes undercover in lady clothes to protect his identity.
His is possibly our favourite outfit choice of all our cross-dressers – never has a former bodybuilder looked so regal in a floor-length pastel pink smock dress. Lets be honest, there’s no way he could ever pass as a lady – he looks exactly like Arnie in a trashy wig, but we love it anyway.
Albert - The Birdcage (1996)
It’s Meet The Parents gone fabulous in this American remake of the equally camp La Cage aux Folles . Albert and Armand (Nathan Lane & Robin Williams respectively) are a happily settled couple who run a gay nightclub, but find themselves in a pickle when their son brings his fiancée’s ultra-conservative family over for dinner.
Albert finds it impossible to play it straight, so drags up to the best of his ability and becomes the matronly ‘Mrs Coleman’. The movie was nominated for a GLAAD Media Award, and was praised for ‘going beyond the stereotypes to see the character’s depth and humanity’, thanks to Lane and Williams’ undeniable chemistry.
Yentl Mendel - Yentl (1983)
Apologies if at any point during this we break into a rousing rendition of ‘Papa, Can You Hear Me?’ Barbra Streisand chops her hair, digs out some men’s threads and heads to find a yeshiva where she can study Jewish scripture and live secretly as a male named Anshel.
This adaption seemed to veer dramatically away from the original ending of the short story, giving Babs a Hollywood ending and love interest, instead of focusing on the gender identity problems Yentl faces in the book.
ngel - Bad Educaction (2004)
Almodóvar’s multi-layered masterpiece saw young heartthrob Gael Garcia Bernal star as a femme fatale type, using his cold cunning to manipulate a former schoolmate of his late brother. He puts in a captivating performance, but we can’t quite shake off the startling resemblance between his blonde-wigged ‘Angel’ and Juliette Lewis.
Dave, Adam & Doofer - Sorority Boys (2002)
What are three strapping young frat boys supposed to do when they’re falsely accused of stealing money from their bros and booted out? Grab mini-dresses and make-up and infiltrate the group as ladies of course!
We think someone was trying to prove a point about that whole objectifying women thing, but it was lost somewhere underneath the barrage of fart jokes and, oh yeah, objectifying women. Good legs on ‘em though.
Divine - Pink Flamingos (1972)
Ah, John Waters. It was this notoriously disgusting film that made a bonafide star out of drag queen Divine.
We’re not even going to go into the various perverse things that occur as we follow the filthiest people in the world fight to retain their title, but we have to agree that Divine earned it thanks to the now legendary, stomach-turning ending.
Albert - Albert Nobbs (2011)
Lead by a powerhouse performance from Glenn Close, Albert Nobbs first appeared onstage back in 1982, with none other than Close as the titular character. The part was undeniably one she felt strongly about, as she campaigned for years to turn it into a film, and it’s evident in her truly moving turn as the dedicated hotel waiter, disguising his true female identity to ensure his continued employment.
Focusing more on the shame and guilt that comes with spending a lifetime living a lie than any comical japes and hijinks, Albert’s story pulls you in from the opening.
Malcolm Turner - Big Momma's House (2000)
For every brave and heartfelt cross-dressed performance there’s a Big Momma’s House.
Martin Lawrence doubles the cheap laughs as he throws on a fat suit underneath his saggy lady lumps and wrinkly stockings. Non-stop gross-out giggles and toilet gags make it Dumb & Dumber meets The Nutty Professor . It ain’t clever, but it definitely is big.
Pretty Much Everyone - The Rocky Horror Picture Show (1975)
It’s a bit of a giveaway that a movie is going to be drag-tastic (it’s a word) when the lead character is an alien originating from the planet Transsexual.
From beginning to end, Richard O’Brien’s musical comedy is crammed full of everybody wearing (and inevitably losing) every kind of clothing. A pure orgy of gender-bending, it’s safest just to grab your corset and fishnets and join in without questioning things.
Viola de Lesseps - Shakespeare In Love (1998)
Shakespeare practically invented the comical cross-dress, with boys dressed as girls, men disguised as women, and even sometimes blokes playing ladies pretending to be blokes. 1998’s Shakespeare In Love went all meta, as Joseph Fiennes’s dashing bard cosied up with his leading man, conveniently played by aristocratic totty Viola de Lesseps (Gwyneth Paltrow).
There’s mistaken identity, false accusations and heartbreak galore, but what we’d really like to know is where Viola managed to procure such a convincing false moustache in the late sixteenth century. She must have had one hell of a wig guy.
Tick, Bernadette & Adam - The Adventures Of Priscilla, Queen Of The Desert (1994)
Three drag queens road-tripping across the Australian outback in a temperamental pink bus called Priscilla? SOLD. And when those three are Elrond, Leonard Shelby and General Zod (the 1978 version), you know you’re in for a good time.
If you’ve never wanted to lip-sync opera wearing a bejewelled gown in a giant shoe on the roof of a bus then watch this film immediately. This will change.
Michael Dorsey - Tootsie (1982)
‘You’re too much trouble… No-one will hire you!’ It was these stern words from his agent that persuaded Dustin Hoffman’s volatile actor Michael Dorsey to grab a wig and a set of pearls and have a bash at being an actress instead.
Yes, it occasionally leans towards slapstick, but there’s no denying it has real heart, as well as making a definite comment about sexism in show-business. Still a classic today.
Patrick "Kitten" Braden - Breakfast On Pluto (2005)
Another movie that takes the crass out of cross-dressing, as Cillian Murphy plays gender-confused Irish schoolboy Patrick ‘Kitten’ Braden, trying to find his way (and his long-lost mother) during the turbulent 70s.
Boasting a stellar cast (seriously, even Bryan Ferry pops up), Kitten’s story is painfully dark at times, as she sinks further into London’s grimy underworld.
Lola - Kinky Boots (2005)
If at first you don’t succeed… start making high heels for transvestites?
Chiwetel Ejiofor puts in a stunning performance as in a part that could so easily have been played for cheap laughs, as Joel Edgerton’s buttoned-up businessman joins forces with Lola – a drag queen performer with legs up to her false eyelashes – to save his family’s sinking shoe factory. Cue plenty of uncomfortable silences as Lola arrives in the dingy Northampton factory in a cloud of glitter…
Victoria Grant - Victor Victoria (1982)
Stay with us on this one. Former nun, nanny and all-round ball of loveliness Julie Andrews plays an impoverished singer who finds herself dressing as a man masquerading as a woman as ‘the world’s greatest female impersonator’. Got it? Good.
The film is carried by a combination of perfect comedic timing, classic farce, and the fact that no-one could figure whether Victor/Victoria was a man or a woman, or if they even really minded either way.
Joe & Jerry - Some Like It Hot (1959)
If the movies have taught us anything, it's that if you're having professional (or indeed personal) problems, dress up as the opposite gender and you'll definitely be in with a chance of sorting them out.
For Jack Lemmon and Tony Curtis, it was a group of angry mobsters out for revenge that prompted them to pick up the frocks and join an all-female band, and the pair of them actually make real knock-outs, with Curtis in particular giving off an elegant feminine glamour that complimented co-star Marilyn Monroe’s overt sexiness perfectly. They also gave us possibly the best final line in cinematic history, but we’re sure you knew that already…
Sylvia - Sylvia Scarlett (1935)
Notorious as one of the most unsuccessful movies of the 30s, lead actress Katherine Hepburn played the titular role, a female con artist who masquerades as a boy in order to escape arrest.
Nevertheless, RKO make-up artist Mel Berns is credited with giving Hepburn a truly spectacular transformation, one that even without all the prosthetics and CGI tricks of today still holds up as convincing.
Noxeema, Vida & Chi-Chi - To Wong Foo, Thanks For Everything! Julie Newmar (1995)
It's that old-fashioned tale of three drag queens on a road trip who end up stranded in a small-minded hick town.
Patrick Swayze, Wesley Snipes and John Leguizamo put in stellar turns as the sequin-clad hopefuls travelling to the 'Miss Drag Queen of America Pageant', and the film shines a light on the abuse faced by those who dare to be different. Major kudos for the emotional Spartacus -esque ending as well.
Film Actor - The Masquerader (1914)
In what is now seen as the original Tootsie , Chaplin's The Masquerader sees him portraying a bumbling actor whose constant gaffes get him booted offset.
Determined to get his screen-time, he realises his only option is to return as Mrs Chaplin and use his feminine wiles to charm the director.
This wasn't Charlie's only appearance as a lady - he pops the dress back on in both A Woman and A Busy Day.
Evelyn Salt - Salt (2010)
Hunted by her former friends and peers, Angelina Jolie's Eva Salt is forced to 'man-up' in order to retain her freedom and clear her name. This also proves to us that one of the world's most beautiful women does NOT make one of the world's most attractive men. Shudder.
Daniel Hillard - Mrs Doubtfire (1993)
Some say that rather than being a heart-warming family comedy, Mrs Doubtfire is actually a terrifying story of obsession, deceit and attempted murder, but we know that there's nothing creepy about a deadbeat dad disguising himself as a woman in order to gain illegal access to his children and poison his estranged wife new beau. Nothing creepy at all...
Viola Hastings - She's The Man (2006)
She's The Man featured Amanda Bynes in her teen movie heyday, and this not-horrendous modern-day adaptation of Shakespeare's Twelfth Night saw her take centre stage to play a girl who dresses up as her own twin brother in order to attend football camp.
We're not quite convinced at the believability of her gender-swap, but apparently it was authentic enough for the campus hottie to fall head over heels, so what do we know?
Kevin & Marcus - White Chicks (2004)
Ok, so it's not what you'd call a 'classic', but the this tale of two bumbling FBI agents who find themselves needing to dress up as two scrawny blonde socialites brought a different level to movie cross-dressing- if you've never seen Marlon Wayans dressed as Anne Dudek then prepare yourself for something reaaally special.
But there are happy endings all round, as the lads realise that wearing heels WHILST shopping isn't as easy as it looks, and feminism gains two new supporters. Hurrah!
Brandon Teena - Boys Don't Cry (1999)
Proving that cross-dressing in movies doesn't always have to mean a bloke in a pair of over-sized fake knockers and dodgy wig, Hilary Swank won critical acclaim (and an Academy Award) when she played real-life trans man Brandon Teena in Boys Don't Cry .
Swank fully immersed herself in the role, wrapping her chest in bandages and stuffing her trousers just as Teena had done - it was convincing enough that her neighbours believed the 'young man' coming to and from Swank's apartment was her visiting brother.
The Stoners - The Life Of Brian (1979)
So you think cross-dressing + Monty Python, and chances are your mind goes straight to a robed Terry Jones croaking 'He's not the Messiah, he's a very naughty boy!' out of a window.
However, our favourite moment has to be the gaggle of frustrated Biblical ladies who stick on unconvincing fake beards in order to attend the stoning of a blasphemous old fella.
Mulan - Mulan (1998)
Not only did Mulan disguise herself as a dude in order to infiltrate the Chinese Army & fight for her father's honour, she did it whilst singing angsty songs about her reflection. Talk about multi-tasking.
She also managed to save the Emperor's life, defeat the Huns and single-handedly convince the entire Chinese Empire that women could do more than cook dinner and have babies. The originator of girl power? We think so.
The Joker - The Dark Knight (2008)
Heath Ledger's dad, Kim Ledger, said about this scene: “The hospital scene is interesting because when he was a kid, his sister Kate liked to dress him up as a nurse."
“He looked pretty funny like that. He looked pretty funny in the film, too.”
We couldn't have said it better ourselves.