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.