14 Actors Who Nailed Roles as the Opposite Gender

14 Actors Who Nailed Roles as the Opposite Gender

Hollywood has long celebrated actors who push boundaries and transform themselves completely for their craft. Some of the most memorable performances in film history come from actors who stepped across gender lines, bringing authenticity, humor, or deep emotion to roles that challenged traditional expectations. Whether for comedy, drama, or social commentary, these performances remind us that great acting knows no limits.

1. Robin Williams — Mrs. Doubtfire (1993)

Imagine losing access to your kids and going to extreme lengths just to see them again. That’s exactly what happens in this beloved comedy where a desperate dad transforms himself into a sweet, elderly British nanny named Mrs. Doubtfire.

Williams brought incredible energy to the role, switching effortlessly between hilarious physical comedy and tender, heartfelt moments. His ability to make audiences laugh one minute and cry the next made this character unforgettable.

The prosthetics and costumes were top-notch, but it was Williams’ genuine warmth that sold the performance. He showed that love can make people do the wildest things, even putting on a dress and wig to stay close to family.

2. Hilary Swank — Boys Don’t Cry (1999)

Raw emotion pours from every scene as this film tells the true story of Brandon Teena, a transgender man living in rural Nebraska during the 1990s. Swank completely disappeared into the role, earning her first Academy Award for the gutsy performance.

Her portrayal wasn’t just about physical transformation—it captured Brandon’s courage, vulnerability, and determination to live authentically despite dangerous opposition. Critics praised how she brought dignity and humanity to a story that could have been exploitative in less capable hands.

The film sparked important conversations about identity and acceptance. Swank’s commitment to honoring Brandon’s memory while delivering a powerful cinematic experience remains one of modern cinema’s most impactful achievements.

3. Dustin Hoffman — Tootsie (1982)

Struggling actors sometimes have to get creative to land roles, but this takes it to a whole new level. An unemployed performer decides to audition as a woman named Dorothy Michaels and ends up becoming a soap opera sensation.

Hoffman’s performance brilliantly balances comedy with social commentary about how women are treated in the entertainment industry. Dorothy becomes beloved by audiences while the actor behind the disguise learns valuable lessons about respect and equality.

The movie became a massive hit and changed how Hollywood viewed gender in storytelling. Decades later, it remains a classic example of how comedy can challenge stereotypes while keeping audiences thoroughly entertained throughout.

4. Cate Blanchett — I’m Not There (2007)

Six different actors portrayed Bob Dylan in this experimental film, but one stood out for sheer audacity. Blanchett took on Dylan’s electric, controversial mid-1960s persona with swagger and attitude that felt completely authentic.

Her performance captured the musician’s rebellious energy, sharp wit, and mysterious charisma without ever feeling like imitation. Critics were amazed at how naturally she embodied this iconic figure, earning Golden Globe and Oscar nominations.

Blanchett studied countless hours of Dylan footage to nail his mannerisms, speech patterns, and even his unique way of moving. The result was magnetic—proving that gender matters far less than talent and dedication when creating unforgettable characters.

5. Jared Leto — Dallas Buyers Club (2013)

Compassion radiates from every scene featuring Rayon, a transgender woman fighting for survival during the AIDS crisis of the 1980s. Leto lost significant weight and completely transformed himself physically and emotionally for this challenging role.

His sensitive portrayal earned widespread acclaim and an Academy Award for Best Supporting Actor. Rayon’s friendship with the film’s protagonist showed how people from different backgrounds can unite against injustice.

The performance sparked conversations about representation and authenticity in Hollywood. While some debated whether transgender roles should go to transgender actors, Leto’s dedication to treating Rayon with dignity and respect created a character audiences won’t soon forget.

6. Eddie Redmayne — The Danish Girl (2015)

Pioneering transgender artist Lili Elbe made history in the 1920s as one of the first known recipients of gender confirmation surgery. Redmayne brought her story to life with delicate, nuanced acting that captured both strength and fragility.

The transformation required extensive physical preparation and emotional depth to portray Lili’s journey from living as Einar Wegener to embracing her true identity. Redmayne earned an Oscar nomination for the demanding role.

Critics praised his commitment while also discussing broader questions about casting and representation. The film introduced many viewers to an important historical figure whose courage paved the way for greater understanding and acceptance decades later.

7. Glenn Close — Albert Nobbs (2011)

Survival sometimes requires extraordinary measures, especially in 19th-century Ireland where economic opportunities for women were severely limited. Close portrays a woman who has lived as a male butler for decades, hiding her identity to earn a living.

Her quiet, restrained performance reveals layers of loneliness, fear, and longing beneath Albert’s carefully maintained facade. Close also co-wrote the screenplay, showing deep personal investment in bringing this story to screen.

The character’s tragic journey highlights historical gender inequality and the sacrifices people made simply to survive. Close’s subtle acting earned her an Oscar nomination and reminded audiences that sometimes the most powerful performances whisper rather than shout.

8. Tilda Swinton — Orlando (1992)

Based on Virginia Woolf’s groundbreaking novel, this film follows a character who lives for centuries, mysteriously shifting between male and female identities across different historical periods. Swinton’s ethereal presence made her perfect for the role.

Her androgynous features and commanding screen presence allowed seamless transitions between genders without heavy prosthetics. The performance explores how society treats people differently based on gender presentation.

Swinton brings intelligence and grace to Orlando’s journey through time, making complex literary themes accessible and visually stunning. The film remains a cult favorite among audiences interested in gender fluidity and unconventional storytelling that challenges traditional narrative structures.

9. John Travolta — Hairspray (2007)

Baltimore in the 1960s comes alive with music, dancing, and a plus-sized, lovable mother named Edna Turnblad. Travolta took on this role originated by drag performer Divine, bringing his own charm and humor to the character

Wearing a fat suit and full makeup, he created a warm, protective mom who learns to overcome her insecurities and support her daughter’s dreams. The performance balances comedy with genuine heart.

Audiences loved seeing Travolta embrace such a playful, unconventional role later in his career. His chemistry with the cast and willingness to dance and sing in drag showed his range and reminded everyone why he became a star in the first place.

10. Cillian Murphy — Breakfast on Pluto (2005)

Charm and resilience define Patrick “Kitten” Braden, a transgender woman navigating the troubles of 1970s Ireland with optimism despite facing constant hardship. Murphy’s delicate, fearless performance earned him a Golden Globe nomination.

His portrayal never mocks or diminishes Kitten’s identity—instead, he presents a fully realized person with dreams, humor, and determination. The film follows Kitten’s search for her mother while surviving prejudice and violence.

Murphy brought vulnerability and strength to the role, creating a character who refuses to let cruelty destroy her spirit. The performance remains one of his most daring and showcases his incredible range beyond the intense roles he’s known for today.

11. Felicity Huffman — Transamerica (2005)

Just days before her gender confirmation surgery, Bree discovers she has a teenage son she never knew existed. This road-trip dramedy follows their awkward, touching journey toward understanding and acceptance.

Huffman’s nuanced performance avoids stereotypes, instead creating a complex character dealing with anxiety, hope, and unexpected family complications. Her careful attention to Bree’s voice, mannerisms, and emotional state earned critical praise and an Oscar nomination.

The film brought transgender stories to mainstream audiences with sensitivity and humor. Huffman worked closely with transgender consultants to ensure authenticity, creating a character whose humanity shines through every scene and resonates with viewers regardless of their background.

12. Tony Curtis & Jack Lemmon — Some Like It Hot (1959)

Witnessing a mob hit forces two musicians to flee Chicago in the most creative way possible—disguising themselves as women to join an all-female jazz band. What follows is pure comedic brilliance.

Curtis and Lemmon commit fully to the physical comedy while maintaining perfect timing alongside Marilyn Monroe. Their exaggerated feminine mannerisms and constant fear of discovery create hilarious situations that still work decades later.

This Billy Wilder classic topped the American Film Institute’s list of greatest comedies for good reason. The duo’s willingness to look ridiculous while delivering sharp performances helped break ground for gender-bending comedy in mainstream cinema.

13. Amanda Bynes — She’s the Man (2006)

When her school cuts the girls’ soccer team, a determined athlete hatches an outrageous plan—impersonate her twin brother and join the boys’ team at his boarding school. Shakespeare’s Twelfth Night gets a modern teen makeover.

Bynes throws herself into the physical comedy, perfecting a deeper voice, masculine swagger, and hilarious attempts at “guy behavior.” Her commitment to the absurdity makes the far-fetched premise work surprisingly well.

The film became a cult favorite among millennials who appreciated its message about gender stereotypes in sports. Bynes proved her comedic chops while the story showed that talent matters more than gender when given equal opportunity to compete.

14. Cate Blanchett — Manifesto (2015)

Returning to this list proves exceptional talent knows no bounds. In this experimental art film, Blanchett plays thirteen wildly different characters, including several traditionally male personas, all delivering artistic manifestos.

She transforms into a homeless man, a punk rocker, a CEO, and more—each distinct and fully realized. The performance showcases her chameleon-like ability to disappear completely into roles regardless of gender.

This ambitious project demonstrates why she’s considered one of the greatest actors of her generation. Her fearless approach to character work and willingness to take risks in unconventional films continues to push boundaries and inspire fellow performers worldwide.