Actors Who Have Done Crossdressing in Films

Crossdressing has always been a popular theme in movies, whether it’s male actors dressing up as female characters or female actors playing male characters. Sometimes, crossdressing is just a subplot in a film, while in other movies, the entire story revolves around the characters who crossdress.

These films not only entertain audiences, but also raise awareness about transgender issues, gender diversity, and sexuality. Countless performances by actors have left a lasting impact on audiences due to their exceptional acting skills and the dedication with which they played their characters opposite to their gender.

In this blog, we will celebrate some of these performances where actors crossdressed to play their roles.

Male Actors Who Crossdressed

Cillian Murphy in the film “Breakfast on Pluto”

Supremely talented Cillian Murphy crossdressed to play the role of a transgender girl named Patricia ‘Kitten’ Braden in a movie. The movie is about Kitten’s journey in London to find her mother, during which she joins a rock band, works with a magician, becomes a prostitute, and works as a dancer. Cillian’s performance was so convincing that I was shocked when I first saw him in the movie. Throughout the movie, he stayed in character and looked like a real trans girl trapped in a man’s body, and OMG, Cillian looked such a diva in costume and makeup. This is not the only movie where Cillian has crossdressed; you can also check out his other movies like Sunburn and Peacock.

Yoo Seung Ho in “Seondal”

I believe Korean men are redefining masculinity, embracing the culture of the flower boy or feminine men. It’s common to see clean-shaven faces with makeup, dyed hair, and girly fashion in Korean pop culture, with actors leading the trend. Yoo Seung, in the movie Seondal, is a perfect example of this. He played a con artist who disguised himself as a woman and did it so well that it left people in awe of his beauty and glamour. He looked amazing in a traditional Korean female outfit, making it difficult to distinguish whether he was a male or female. I think because of genetics, Korean men are genetically well-suited to crossdressing, and if you like crossdressing or crossdressers, this movie is a must-watch.

Lee Pace in the movie “Soldier’s Girl”

I can never forget Lee Pace’s character of Calpernia Addams in the movie Soldier’s Girl. The movie is based on the life of a transgender woman who works as a showgirl. Despite being a masculine man, Lee Pace portrayed the character of a trans woman so beautifully that he looked stunning on screen. The movie highlights the love story of a straight man and a transgender woman and also raises awareness about the struggles and harassment that trans people face. The ending is very sad and leaves a deep impact on viewers.

Jared Leto in “Dallas Buyers Club”

When it comes to gender-neutral fashion, Jared Leto is the first name that comes to my mind. The actor has proven his stance on gender and fashion in multiple instances. Whether it’s movies or photoshoots, the actor always comes out very confident as an androgynous star. In the movie Dallas Buyers Club, Leto played the role of a transgender character named Rayon. Reports say that he lost 30 pounds to get into the character’s skin. His dedication paid off when he won an Oscar for Best Supporting Actor that year. Even though the movie has divided opinions, it is still a must-watch.

Adam Sandler in “Jack and Jill”

Extremely funny Adam Sandler starred in Jack and Jill, where he crossdressed to play his own twin sister in the movie named Jill. Jack, played by Adam Sandler, is a businessman who is very sensible by nature, and on the contrary, Jill, who is also played by Adam Sandler, is a hyperactive strong-built woman who does weird and funny things in the movie.

The movie does not have any social commentary, so don’t expect anything heavy. It’s a lighthearted, funny movie that can make you laugh on a tough day as a crossdresser. Seeing a big star like Adam Sandler do crossdressing in public also shows that there is nothing wrong with crossdressing, and if you are someone who likes crossdressing, you shouldn’t feel ashamed of it.

Eddie Redmayne in “The Danish Girl”

The movie is based on the true story of a Danish painter named Lili Elbe, who was the first known person to undergo sex reassignment surgery. Eddie Redmayne played the character with such authenticity that he won an Oscar for his performance. He didn’t just crossdress and apply makeup. He immersed himself in the role of a transgender woman and impressed everyone. Eddie portrayed feminine behavior so accurately that he looked flawless on screen. However, he did receive some backlash for being a cisgender playing a trans character on the screen, which should’ve been played by a trans person. I think this criticism was a bit unfair to the actor and his capabilities. Eddie did exceptional work, and this movie is a must-watch for everyone.

Female Actors Who Crossdressed

Tilda Swinton in “Orlando”

Tilda Swinton is famous for her unique and versatile acting skills and her androgynous looks. In the movie Orlando, she played a character who defies the traditional notions of gender and sexuality. The story is based on the novel by Virginia Woolf, in which the protagonist is ordered by the queen to remain forever young. The character lives through many centuries and experiences life in multiple genders. This movie is highly respected in the transgender community because of its portrayal of the character, especially Orlando, played by Tilda Swinton.

Cate Blanchett in the film “I’m Not There”

Cate Blanchett surprised everyone with her role in the movie “I’m not there” where she played the legendary musician Bob Dylan. The movie features six different actors portraying six different stages of Dylan’s life, including Christian Bale, Heath Ledger, Richard Gere, and Ben Whishaw.

Despite being known for her stunning and sexy looks, Blanchett showed off her acting skills by convincingly portraying a male character like Bob Dylan. The movie is a must-watch for fans of Cate Blanchett.

Hilary Swank in the film “Boys Don’t Cry”

In this movie, Hilary Swank played the character of an American trans man who was murdered and raped. She won Oscars for her amazing acting skills and established herself as a great actor in Hollywood. The story of this movie is very emotional and heartbreaking, anything extra could have looked over dramatic on screen. However, Hilary portrayed the character with such great subtlety that it left a deep impact on the audience and critics.

Amanda Bynes in “She’s the Man”

If you enjoy Amanda Bynes and American high school romantic comedies, then you should watch this movie. In this film, Amanda Bynes disguises herself as her brother to attend a boarding school and play on the boys’ soccer team. As the movie progresses, she falls in love with her brother’s hot roommate. While this movie may not have received critical acclaim, as a crossdresser, you’ll love Amanda Bynes’ portrayal of a high school boy.

Gwyneth Paltrow in the movie “Shakespeare in Love”

Many of us recognize Gwyneth Paltrow from her role in Iron Man as Pepper Potts, but few know that she is also crossdressed in the movie Shakespeare in Love. In this film, Paltrow played the role of Viola De Lesseps, a woman who wanted to perform on stage during a time when only men were allowed to be actors. With the help of makeup and crossdressing, she becomes a male character named Thomas Kent and auditions for Shakespeare, eventually getting the part. The movie is a beautiful romantic tale that came out in 1998 and was directed by John Madden. After this movie, I’m sure you will have more love for Gwyneth Paltrow as an actor.

Conclusion

As I mentioned earlier, actors have been challenging themselves to portray unique characters since the beginning of acting and stage drama, whether it involves crossdressing or exploring sexuality. In the past, the audience used to get uncomfortable with these concepts, but nowadays, even the audience welcomes movies that challenge their thought processes and show something unique and new.

As an audience, we have started to accept crossdressing, homosexuality, and gender diversity in movies, which is a good thing. This not only gives freedom to movie makers to think outside of the box but also teaches society about gender and sex. With the help of this blog, I tried to recommend some crossdressing content for you guys so that you can watch and appreciate crossdressing and gender diversity.