Since the inception of drama, people have always experimented to create something unconventional on screen and though initially the unconventionality may not have been welcomed by most audiences, over time they did learn to appreciate its presence. Theatre has always been the first medium to display such changes and stage actors, known for their diligence and eagerness to explore every opportunity, were the earliest artists to switch genders for their portrayals. The first traces of cross-gender acting can be noticed in Shakespeare’s works, especially ‘The Merchant of Venice’ and ‘As You Like It’ that feature female characters cross-dressing to progress in an oppressive society. During the same period, the extravagant Japanese Kabuki theatres introduced “onnagatas” or male actors who played women’s roles and “wakashu” or female actors who specialized in adolescent male roles, in plays that dealt with themes regarding male homosexuality.
As usual the English speaking industry showed reluctance and it was only after cross-gender performances by some acclaimed actors, people started to pay attention towards the role of cross-dressing in entertainment culture. Though the cross-gender roles in today’s movies are written by vagabonds, who believe lame sexual innuendos can make up for lack of creativity, we can look back at the independent features that intend on acknowledging audiences with the truth. As of now, there has been a massive change in the relevance of such roles, from existing for comical and dramatic effect till the 90s to revealing the atrocities faced by cross-dressers and sexually conflicted people.
Crossdressing has always attracted attention, be it in real life or in reel. And moviemakers have experimented with this theme in films that required a man to play a woman or vice versa, ever since the idea struck them. In olden days, when women were not given enough freedom to step out of the house (and that was prevalent everywhere in the world, not just in India!), men got into women’s costumes to play the part and boy, they performed well too! Since then, the trend of male actors getting into gowns to play a crossdresser has only seen positive changes in movies.
Now, I understand that some choices on the list might be controversial and I also assume that different sections may have varying opinions on them, but let me remind you the primary criteria is the effectiveness of the performances on a critical and emotional level. So here is the list of top crossdressing movies ever. You can watch best cross gender movies on Netflix, Hulu, or Amazon Prime.
16. She’s The Man (2006)
When Sebastian leaves for London to pursue his musical dreams, his twin sister Viola takes his place in his boarding school, eventually going on to win his soccer coach’s trust during a series of tryouts and also dates (while still cross-dressed), much to her own chagrin and churning of emotions inside. Andy Fickman’s ‘She’s The Man’, starring Amanda Bynes fared well at the box office and audiences loved the actress’s transformation into a man, which she pulled off with great ease.