It has always been a common staple of comedic cinema to put a man in a dress. From Curtis and Lemmon in Billy Wilder's seminal Some Like It Hot back in 1959, to Dustin Hoffman in Tootsie
, to Tim Curry's “sweet natured transvestite” in The Rocky Horror Picture Show
, to modern days spoof like the Big Momma movies and Adam Sandler's Jack and Jill
, there is a proven box office draw in having a well-known
male lead dress up as a woman for laughs. What is less common is the reverse cross dressing film – where women “butch it up” as men - in mainstream cinema. Looking back at the occasions when they do, it is striking to note that rather than the film's being comic they are almost always serious and, in many cases, tragic in nature.
This year saw Glenn Close nominated for an Oscar for her role as the title character in Albert Nobbs, the story of a 19th Century Irish woman posing as a male butler. Close's Nobbs is not a laugh a minute spoofer like the characters mentioned above but rather a tortured soul, out of place and misunderstood by a repressed society. This is a common theme in films of this sort and its lineage can be traced back through the sub-genre.
Typical of the seriousness with which female cross dressing is taken is 1999's Boys Don't Cry which tells the shocking true story of Brandon Teena, an American teenaged girl who passed herself off as a boy but was then violently and viscously assaulted when her secret was revealed. Hilary Swank won an Oscar for her brilliant portrayal of Teena and the film did much to highlight the still evident homophobia which simmers beneath the surface of Western society.
That is not to say that Hollywood has never played female cross dressing for laughs (look at 2006's Twelfth Night update She's The Man, in which Amanda Byrne poses as a man to get on the soccer team) just that the times when it does are few and far between. In general when it comes to women dressing as men, Hollywood reckons it is a serious business.