7 Crossdressing Female Roles Played by Male Actors ...

In the 1950s St Trinian's movies, headmistress Miss Fritton was played by Alastair Sim. This crossdressing casting was imitated in the remakes with an unrecognisable Rupert Everett as Miss Fritton. Both actors also played Miss Fritton's brother, but they are most amusing as the headmistress who is every bit as anarchic as her students.

The majority of Divine's screen roles were female characters, although he did occasionally play a male role. Personally, I much prefer his version of Hairspray's Edna Turnblad, the gargantuan Baltimore housewife, to any other. The role has been performed on stage, as well as in the remake by John Travolta.

The title character in Orlando changes sex in the story, moving between male and female. But Queen Elizabeth I, who was most definitely female, is here played by Quentin Crisp, the famously camp writer and raconteur. It's an extraordinary piece of casting, yet works very well, as the amount of makeup Crisp had to wear ties in with the heavy cosmetics used by the Queen as she aged.

Alec Guinness not only played a female role in this classic black comedy, but eight different members of the same family. Among them was the imperious Lady Agatha, who comes to a sticky end while in a hot air balloon. It's so much fun that it's rather a shame he didn't play more female roles in the movie.

In a nod to the tradition of female roles being performed by men on stage, theater actor Mark Rylance played the part of Olivia in Twelfth Night. In this production, all the parts were played by men. But it's not Rylance's only female Shakespearean performance - he's also played the title role in Cleopatra.

It's perhaps not that surprising that comedian Jerry Lewis also tried his hand at playing female roles. In The Patsy, as well as the main (male) character, he also performed as an extraordinarily ugly female backing trio (don't watch the clip … it's scary). He also played his main character's mother in The Ladies Man, and a female character in Three On A Couch, one of five roles he played in the movie.

The Monty Python team spent half their time of screen playing female roles. Perhaps one of the finest was Brian's fearsome mother in the biblical satire Life Of Brian. With memorable lines like 'He's not the Messiah, he's a very naughty boy!' and 'There's no Messiah here. There's a mess alright, but no Messiah', Brian's mother pretty much steals the movie.

These roles are all definitely female characters. There are also plenty of 'men in drag' roles such as 'Some Like It Hot', where we're not meant to believe that the character is female. What is your favorite cross-dressing role on screen or stage?