12 Stars Who Embraced Both Their Feminine and Masculine Side and Will Have You Look Twice

Actors in Shakespeare’s day would cross-dress as women in order to play female roles. Nowadays, many actors dress as a different gender to challenge themselves, shake up stereotypes, and stretch the minds of their audience. Though it’s not easy to transform from the feminine to the masculine side or vice versa and nail the role convincingly, these 12 stars were brave enough to do both. In fact, some of them even wound up winning prestigious awards for their efforts.

The Bright Side team has collected a list of stars who shine at both extremes of the gender spectrum for you to enjoy.

1. Jared Leto as Rayon

The actor portrays the transgender woman Rayon in Dallas Buyers Club, a film based on a true story. In preparation for the role, he lost 30 pounds and waxed his body. His efforts weren’t in vain since the movie was a massive success and earned him an Academy Award for Best Supporting Actor.

2. Woody Harrelson as Galaxia

The movie Anger Management is about a mild-mannered man who is involved in an incident on an aircraft and is sent to anger management sessions in order to avoid going to jail. During the film, Galaxia, played by the well-known actor Woody Harrelson, made a brief yet memorable appearance.

3. Jude Law as Minx

Rage tells the story of a young blogger at a New York fashion house who uses his phone to film behind-the-scenes interviews. Jude Law shows his feminine side through the character Minx, an attractive transsexual supermodel. Preparing for this role wasn’t a piece of cake for sure. He said that it took him several hours to remove his body hair since he’s not a fan of waxing.

4. Eddie Murphy as Mama Klump

The Nutty Professor and Nutty Professor II star Eddie Murphy in 7 different roles, including Mama Klump. This isn’t the first time he has portrayed characters from different genders and backgrounds. With his talent, combined with prosthetics and excellent hair and makeup, he often plays multiple characters that are almost impossible to identify.

5. Martin Lawrence as Big Momma

Laurence plays FBI agent Malcolm Turner in the 2000 crime comedy film Big Momma’s House. He was sent on a mission to capture the notorious criminal Lester Vesco and is led, through a series of events, to take on the identity of an old woman named Big Momma.

6. Glenn Close as Albert Nobbs

The actress depicted a 19th-century woman who disguised herself as a man in order to work as a butler in the 2011 British-Irish drama Albert Nobbs. Glenn Close underwent an incredible transformation so that she could play a character who was pretending to be someone of a different gender. Her role in this film earned her numerous awards, including Best International Actress and 3 Oscar nominations.

7. Meryl Streep as The Rabbi

One actor who was so convincing in a cross-dressing role that you would never have guessed it was her is Meryl Streep. In the 2003 HBO miniseries Angels in America, Streep portrayed an elderly rabbi who visits the bedridden protagonist to hear his confession. Thanks to the makeup, wardrobe, and hair department and Streep’s talent, she became unrecognizable. Meryl Streep won an Emmy Award for Outstanding Lead Actress in a Miniseries or Movie for her performance.

8. Tyler Perry as Madea

Tyler Perry is arguably best known for his Madea character, who has been featured in multiple movies and plays since 2005. The outspoken woman, often described as a “gun-toting grandmother of immense girth,” has made quite a name for herself over the years. A Madea Homecoming marked the debut of the now-iconic character in Tyler Perry’s stage productions. In it, we see Madea and her sister Bam debating what to do with their brother Joe’s ill daughter and granddaughter after he is sent to jail.

9. Michael J. Fox as Marlene McFly

This ’80s classic has been hailed as an important film by critics and fans alike. In the film, a teenager accidentally travels back in time to 1955 to meet his parents as teenagers and ensure that they will fall in love. In one, Fox cross-dressed as Marlene McFly, a feminine blond character. This movie allows Michael J. Fox to shine through as an actor, and it proves why the movie won the People’s Choice Award for Favorite Movie.

10. Tilda Swinton as Orlando

Orlando is a non-linear fantasy film directed by Sally Potter that is based on Virginia Woolf’s novel. It is a non-linear fantasy about an immortal person that transforms from male to female, and lives in multiple ages. Tilda Swinton’s portrayal of Orlando provided an opportunity for the actress to demonstrate her versatility as a performer. As a result, she was nominated for a Golden Globe Award for Best Actress in 1993.

11. John Lithgow as Roberta Muldoon

The World According To Garp is about a writer named Garp who was given up for adoption because of his sexual identity. One of the most interesting roles in the movie is Roberta Muldoon. Roberta Muldoon is Grap’s childhood friend and first love who makes him realize he’s attracted to males and females. In recognition of his heartfelt acting, John Lithgow earned an Academy Award nomination for Best Supporting Actor.

12. Taylor Swift as The Man

Sometimes the best way to convey a message is to walk a mile in someone else’s shoes. In her music video, she takes aim at toxic masculinity by showing 2 sides of Swift (the one we know and her male alter ego). By the end of the video, we can see how they used prosthetics to make the changes.
First, they built up her jawline and cheekbones using padding around her neck and chin. Then, they placed pieces over her face. Later, they applied makeup focusing on the eyebrows and the jawline. Lastly, they glued down her hair. This jaw-dropping transformation took between 4 to 6 hours.

Have you tried cross-dressing before? Which actors do you believe took cross-dressing to whole new levels in order to deliver a powerful performance?