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.