Written by Lily Davis.

Whether it be squeezing into a frilly corset or tightly binding down a chest, we take a look at some of the finest films featuring cross-dressing. We revisit the most memorable performances from those brave enough to tackle characters they may not be all too familiar with. With quirky, fun and fascinating results. Also, if spoilers really grind your gears then watch out for a few in here. Here are the Top Ten Cross-Dressing Performances…

10. Shakespeare in Love (1998)

This film plays with the idea that in Elizabethan theatrical society it was men who played all female characters. Joseph Fiennes plays a young William Shakespeare struggling with his work in the theatre. His luck changes when he stumbles across the exquisite Viola De Lesseps, played by Gwyneth Paltrow. The twist is that she is disguised as a man so she can participate in the world of theatre, which is otherwise dominated by men. As Shakespeare discovers Viola’s secret, and promptly falls madly in love with her, the plot complicates further. Gwyneth Paltrow is captivating in the role. Despite being one of the prettiest boys you’ll see, she manages to fool those around her. Her portrayal is earnest and even won her an Oscar that year. Also, for Shakespeare nerds there is a delightful range of references to many of his plots and characters.

9. Bad Education (2004)

This is not Pedro Almodóvar’s first film dealing with transvestites. The Spanish filmmaker has often explored the theme of sexuality throughout his extensive career. Yet there is something unique and memorable about Bad Education. The story is complex and multi-layered; it skips back and forth between the past and present. In a very broad sense it is about two old school friends, their own experiences and how their lives intersect. One of these men is Ignacio, also known as Zahara when dressed in drag. Gael García Bernal slips on the dress for this role and has an extraordinary screen presence. His portrayal of this complex character is absolutely outstanding. Bernal looks the part as well and executes it with a sense of grace. Almodóvar’s melodramatic style works perfectly with the content of the film. Bad Education is alive with a strong sense of vibrancy and passion typical of Spanish culture. This energetic film is thought-provoking and powerful.

8. Transamerica (2005)

Transamerica navigates the journey of Bree Osbourne, a man undergoing a sex change to become a woman. This idea becomes more convoluted as actress Felicity Hoffman, famously known for Desperate Housewives, plays this character. Hoffman is a woman playing a man who desires to be a woman. Luckily, due to the integrity and strength of Hoffman’s performance, this fact is left in the dust after just a few minutes of screen time. She embodies the role with such authenticity that it’s easy to forget we are watching a performance. This was recognised through Hoffman’s nominations at both the Academy Awards and Golden Globes. While many of the films on this list combine the theme of cross-dressing with comedy, Transamerica takes a different approach. Director Duncan Tucker delves into the tough reality of sexual re-orientation surgery. Unique and highly engaging.

7. The Rocky Horror Picture Show (1975)

Let’s be honest, when we think of Rocky Horror there’s one particular image that surely comes to mind: Tim Curry decked out in fishnet stockings, high heels and a corset. It’s an image that definitely imprints itself in your memory. The same can be said for much of The Rocky Horror Picture Show. It’s the kind of film that’s difficult to tear your eyes from and certainly makes an impression. There’s a reason this film is constantly revisited as a cult classic. This musical parody bends the parameters of sexuality. The whole experience is rollicking good fun. We follow do-gooders Janet and Brad as they are dragged into the sexually elusive and monstrously exciting world within Dr Frank N. Furter’s home. This film has charmed audiences for decades and a large part of that is linked to Tim Curry’s performance. His extravagant and mesmerising characterisation is simply unforgettable.

6. The Birdcage (1996)

Originally an adaptation of the Broadway play La Cage Au Folles, The Birdcage sure is one enjoyable film. Nathan Lane and Robin Williams play partners who successfully run a drag bar in South Miami Beach. Anxiety begins to mount when their son Val announces his engagement to a girl with highly conservative parents and the two families must come together. What ensues is hilarious good fun. You will be torn between biting your nails and outbursts of laughter watching Lane attempt to convince his guests of his womanhood. While the characters in this film may initially feel obliged to conceal who they truly are, they soon learn otherwise. Here lies the heart-warming message at the centre of the film. The Birdcage celebrates difference and acceptance, which is of the utmost importance. It communicates this through a highly enjoyable comedy, which will appeal to all. Look out for the hilarious antics of Hank Azaria as the housekeeper, he’s hard to miss sporting short shorts and tank tops.

5. Mrs. Doubtfire (1993)

I doubt there was any child that watched Mrs. Doubtfire and didn’t pine for a housekeeper just like Robin Williams in drag. Williams plays a father of three, who struggles to see his children after the messy end of his marriage. His solution? To pose as Mrs. Doubtfire, an elderly woman with a knack for minding children. More specifically, his children. This is good old-fashioned family fun and Williams shines in the role. He brings the character of Mrs. Doubtfire to life with a ripe sense of humour, while simultaneously conveying the deep love this father has for his children. The film is genuinely heart warming. It is about a man driven to great lengths to be a part of his children’s lives. And he definitely succeeds. Mrs. Doubtfire is so convincing that she even has her own family fooled.

4. Boys Don’t Cry (1999)

Director Kimberly Peirce tells the story of a young woman who would simply rather be a man. Meet Teena Brandon, who cuts her hair and adopts male clothing to become Brandon Teena. What makes this story so powerful is that it’s true. Hilary Swank plays Brandon and even possesses a startling likeness to him in reality. She portrays him with a great sense of sensitivity and integrity, an important factor given the tragic events that unfold within the story. Brandon makes the move to Falls City where he falls for Lana (Chloe Sevigny). It is here that two young men, rich with ignorance, proceed to brutally attack Brandon. After the police fail to act in the proper manner, Brandon is murdered just two days later. This horrific story shows us the problem with insensitivity and hate. Hilary Swank is absolutely outstanding. She was awarded an Academy Award for her portrayal, which was undoubtedly deserved. It’s a reminder in humanity that we shouldn’t forget.

3. The Adventures Of Priscilla, Queen Of The Desert (1994)

This Australian classic is loud, glitzy and hilarious. The entire film bounces to the beat of ABBA and lights up the eyes with the sparkle of sequins. Hugo Weaving, Terence Stamp and Guy Pearce play three drag performers who decide to make the perilous journey to Alice Springs for a show. The casting is fantastic, with each actor bringing so much charm to their role. The way they playfully make fun of each other is hilarious. The film really taps into the Australian sense of humour, which is perfectly coupled with the Australian drag scene.
The costume and make-up design is truly spectacular. It’s a delight to marvel at the extraordinary drag sequences, of which there are plenty. However, this film isn’t without its darker moments. As the three queens venture further into the outback they are often met with cold ignorance and even violence. Writer-director Stephan Elliot doesn’t shy away from these moments, but the film ultimately promotes acceptance. All the while sucking you into the glitz and glamour of the drag world.

2. Some Like It Hot (1959)

This 1950s comedy has certainly stood the test of time. Jack Lemmon and Tony Curtis play two struggling musicians who, after witnessing a mob attack, dress as women to join a travelling female band. Complications unfold when both become romantically entangled and even find that the mob is on their tail. Both actors take to these roles with a great sense of flair. Although they might occasionally be disgruntled about it, in many ways they truly embrace their feminine sides. Fashioning frilly dresses and garters, the pair fit in seamlessly with their giggling musical troupe. The film is genuinely hilarious. This mostly stems from the comedic timing of the pair, especially when put together. Their relationship, packed with fast-paced bickering, is so much fun to watch. It’s highly enjoyable to witness Lemmon and Curtis flicking back and forth between their male and female personas. They do so with an ease and zest that – over 50 years later – will still have you in stiches.

1. Tootsie (1982)

The number one spot is reserved for Dustin Hoffman’s memorable portrayal of Michael Dorsey turned Dorothy Michaels. Hoffman plays an out of work actor who has the idea to audition for a soap opera, but with one major catch. The part is specifically for a woman. This is no deterrent. He transforms himself into the likeable and spirited Dorothy Michaels and suddenly the part is his. What follows is a screwball comedy with a real human feel. This is achieved with the help of a wonderful supporting cast including Bill Murray, Teri Garr and love interest Jessica Lange. The entire film has a bright and lively feel that mirrors Dorothy Michael’s character. This is a testament to the acting capabilities of Dustin Hoffman. He certainly isn’t the first actor to put on a pair of heels for a role, but he approaches the character with great energy. He truly embodies this female persona. You even develop quite a soft spot for the fictional Dorothy. The fact that Hoffman is playing a talented actor certainly aids the believability of his transformation. This character’s obvious transformation aside, Michael Dorsey also changes by becoming a better man, having understood what it is like to be a woman. A highly enjoyable film with the perfect mix of heart and comedy.

– L.D.

  You May Also Like: