13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters

Olu Ojo
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From Shakespearean times to contemporary cinema, there have been instances where actresses have stepped into male roles, shattering the traditional boundaries of gender. The commitment, hard work, and sheer artistry required for such roles make these performances stand out. Here’s a curated list of ten instances where leading actresses dazzled audiences with their transformative roles.

Mariah Carey’s Dual Role

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
U.S. Air Force via Wikimedia Commons

When Mariah Carey released the music video for “Obsessed,” fans were in for a surprise. Inspired by the movie Mean Girls, Carey portrayed not only her glamorous self but also a male stalker, showcasing her versatility beyond her vocal range.

Angelina Jolie as Evelyn Salt

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Georges Biard via Wikimedia Commons

In the action-packed thriller Salt (2010), Angelina Jolie dons multiple disguises. One of the most striking is when she masquerades as a man, proving her adaptability and skill as an actress.

Gwyneth Paltrow’s Oscar-winning Performance

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Andrew Halpern via Wikicommons

Shakespeare in Love presented Gwyneth Paltrow as Viola de Lesseps, a woman posing as a male actor named Thomas Kent. Paltrow’s riveting portrayal fetched her several accolades, including the prestigious Oscar.

Hilary Swank’s Moving Act

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Dick Thomas Johnson via wikimedia Commons

In the poignant Boys Don’t Cry (2000), Hilary Swank took on the challenging role of Brandon Teena, a transgender man. The film and her performance, laden with depth and empathy, received widespread acclaim.

Kathy Burke’s Unrecognizable Transformation

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Kevin & Perry Go Large via imdb.com

Many were left astonished to realize that Perry from Kevin & Perry Go Large was, in fact, played by actress Kathy Burke. It’s a testament to Burke’s chameleon-like acting abilities.

Elle Fanning’s Brave Portrayal

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Harald Krichel via Wikicommons

In 3 Generations (2015), Elle Fanning brought to life the character of Ray, a teenager undergoing gender transition. This emotionally charged performance showcased Fanning’s maturity as an actress.

Blanca Portillo’s Religious Avatar

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Almagro Festival via Wikicommons.com

The historical epic Alatriste (2006) had Blanca Portillo playing Friar Emilio Bocanegra, a performance which blended gravitas and nuance.

Amanda Bynes’ Sporty Double Act

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
The Heart Truth

Comedy She’s the Man (2006) saw Amanda Bynes play Viola Hastings, a character who impersonates her brother to join a soccer team. Bynes’ comedic timing was spot-on, making the movie a hit.

Cate Blanchett’s Ode to Bob Dylan

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Popperipopp via Wikicommons.com

In I’m Not There, Cate Blanchett channeled the enigmatic Bob Dylan in one of his life’s phases as Jude Quinn. This transformative act earned her a Golden Globe and several nominations.

Linda Hunt’s Groundbreaking Performance

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Red Carpet Report via Wikicommons

1982’s The Year of Living Dangerously brought forth Linda Hunt as Billy Kwan. Her commitment to the role, including altering her appearance significantly, won her an Oscar for Best Supporting Actress.

Whoopi Goldberg’s Classical Stint

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Rainforest Action Network via Wikicommons.com

In a playful nod to tradition, Whoopi Goldberg disguises herself as a white male opera singer in Sister Act 2: Back in the Habit (1993). It’s a comedic moment, showcasing Goldberg’s knack for perfectly timed humor.

Julie Andrews’ Regal Disguise

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
Eva Rinaldi via Wikicommons.com

Long before many on this list, Julie Andrews graced the silver screen as Victoria Grant, a singer who masquerades as a male impersonator in Victor/Victoria (1982). Andrews’ impeccable comic timing, coupled with her vocal prowess made this a performance for the ages.

Barbra Streisand’s Yentl

13 Iconic Movie Roles Where Actresses Masterfully Played Male Characters
NIH Image Gallery via Wikimedia Commons.com

In Yentl (1983), Barbra Streisand portrayed a young Jewish woman who disguises herself as a man to study in a yeshiva. This heartfelt narrative, coupled with Streisand’s emotive performance, offers a compelling exploration of identity and love.

It’s not just about makeup and costumes; it’s the embodiment of the character, understanding their psyche, and delivering it on the screen that makes these performances memorable. Were you surprised by any of these transformations?

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Author

  • Olu Ojo

    My name is Olu. I am a passionate entrepreneur who loves to write about Pets, Home Improvement Hacks & Products, Fitness, and Travel Lifestyle. I have two bachelor's degrees in Veterinary Medicine and Applied Accounting with a CPA designation. I currently shuffle time between completing a Master of Business Administration Degree Education, Professional Practice, and Content writing. I have freelanced lifestyle content and posts for many top authority websites like MSN, and Wealth of Geeks.

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