All the Celebrities Who Have Dressed in Drag Over the Years

Drag is an art form that's as old as time itself. From Shakespearean plays to modern-day films, cross-dressing has always been a source of entertainment for us humans.

Recently, however, there's been a lot of anti-trans hysteria being spewed by certain Republican representatives, which is just downright silly when you consider how long we've been enjoying drag as harmless entertainment as a society.

Celebrities from Mick Jagger to Patrick Swayze, and just about every A-lister in-between have tried their hand at donning a dress and high heels in the name of a good time. So get your panties out of a twist, and let's just enjoy the show!

Ah, Bosom Buddies, the 1980 sitcom that gave us Tom Hanks in drag before RuPaul's Drag Race was even a twinkle in Ru's eye. Some viewers found it hilarious, while others were less than impressed with the show's approach to LGBTQ+ representation.

It definitely won't go down in history as a socially progressive masterpiece, but Bosom Buddies did have devoted fans. Plus, let's be real: who can resist a show that features Hanks in full-on diva mode?

The beloved 70s sitcom M*A*S*H pushed boundaries with its characters, including male soldiers dressed in drag for comedic effect. The most memorable instance was Corporal Klinger, played by Jamie Farr, who donned women's clothing in an attempt to leave the military for mental illness.

While critics argue that drag humor is problematic, M*A*S*H was praised for addressing controversial topics and challenging societal norms. The show's portrayal of gender-bending characters helped popularize the concept in popular culture, breaking down barriers and leaving a lasting impact on entertainment. 

In the 1995 blockbuster To Wong Foo, Thanks for Everything! Julie Newmar, Patrick Swayze stole hearts as Vida Boheme, a charming drag queen who embarks on an epic road trip with two other divas to compete in a California pageant. As part of their plan, the fabulous trio assumes identities as women, dressed to the nines in stylish and stunning ensembles that ooze glamour.

Swayze's unforgettable portrayal of Vida exudes sensitivity and grace, elevating the role's depth and complexity. While some critics have questioned the film's impact on perceptions of the LGBTQ+ community, Swayze and the cast are credited for their entertaining and inspiring performances, which uplift drag queens to mainstream audiences.

Jared Leto is a man of many talents, but his performance as Rayon in Dallas Buyers Club was truly transformative. Leto went all out for this role, shedding pounds and slipping into drag to portray a transgender woman living with HIV/AIDS in the '80s.

His dedication paid off, as Leto received rave reviews and numerous awards for his performance, including an Academy Award for Best Supporting Actor. Leto's attention to detail and willingness to fully embody Rayon's identity left an indelible impression on audiences, proving once again that he's more than just a pretty face.

It's hard to believe that it's been over 60 years since the release of Some Like It Hot, where Jack Lemmon plays the character of Jerry, a struggling musician who, along with his friend Joe, witnesses a mob hit and must go on the run from the mobsters. To evade the gangsters, they disguise themselves as women and join an all-female band, with Jerry taking on the persona of a flamboyant and carefree character named Daphne. 

Lemmon's portrayal of the flamboyant Daphne is still as hilarious today as it was back then. Lemmon's decision to don a wig and high heels was a stroke of comedic genius, and it's no wonder that it was initially met with resistance from the producers. But the risk paid off, and Some Like It Hot remains a timeless classic that's still talked about and imitated today.

Who could forget Nathan Lane's showstopping performance in drag as Albert in the 1996 film, The Birdcage? Lane's transformation into the flamboyant and high-strung partner of Armand (portrayed by Robin Williams) was not only hilarious, but also brought a new level of depth and understanding to the LGBTQ+ community.

When Lane donned a wig and high heels for the role, critics weren't quite sure what to make of it. But Lane's performance was so electric, even the harshest of critics had to admit he slayed in drag. And let's not forget the audience, who gobbled up every moment of Lane's on-screen transformation.

Hollywood has always been a breeding ground for controversy, and The Danish Girl was no exception. Eddie Redmayne's performance in the film, portraying the character of Lili Elbe, one of the first known transgender women to undergo gender reassignment surgery, earned him praise for his sensitivity and nuance. However, the casting of a cisgender, straight man for the role was met with criticism, as many felt it perpetuated a pattern of trans erasure in Hollywood.

Despite the debate, the film went on to receive several Oscar nominations, including a Best Actor nod for Redmayne. Whether you hailed the decision or felt it was a missed opportunity, there's no denying the impact The Danish Girl had on the larger conversation surrounding trans representation in film.

In 1993, the beloved Robin Williams graced our screens as the hilarious and heartwarming character of Mrs. Doubtfire. Williams portrayed a divorced father who would go to any lengths to spend time with his children, including dressing up as a British female housekeeper. The movie was an instant success, receiving rave reviews from audiences and critics alike.

It's no surprise Williams's comedic performance stole the show, but what many may not know is that the transformation into Mrs. Doubtfire was no easy feat. The extensive prosthetic makeup and costume design that took over four hours each day to apply successfully turned Williams into the delightful and convincing character that we still know and love today. Mrs. Doubtfire is a classic film, reminding us of Williams's immense talent and leaving us with an undeniable sense of nostalgia.

John Travolta's performance as Edna Turnblad in the 2007 movie musical Hairspray was nothing short of iconic. With his natural comedic timing and impeccable physicality, he brought this larger-than-life housewife to unforgettable heights. Garnering a Golden Globe nomination for Best Actor in a Musical or Comedy, Travolta's performance was met with both praise and criticism from the public and critics alike.

Some questioned the decision to cast a straight male actor in a role that previously originated with a drag queen, and Travolta himself admitted to putting his own unique spin on the character. But despite any controversy, Hairspray became a box office hit, and Travolta's portrayal of Edna Turnblad has become a timeless and unforgettable part of musical theatre and film history.

Join Noxeema Jackson and two other fabulous drag queens on the ride of their lives! In the 1995 classic To Wong Foo, Thanks for Everything! Julie Newmar, Wesley Snipes brought to life the confident and glamorous character of Noxeema, who sets out on a road trip to compete in a drag queen pageant in California. Dressed in extravagant and eye-catching outfits, the drag queens embrace their feminine sides, taking on new identities as women.

Snipes's performance captures Noxeema's charm and humor, and despite criticism for perpetuating LGBTQ+ stereotypes, Snipes and his co-stars shine in their roles and bring a positive and empowering representation of drag queens to mainstream audiences.

Dustin Hoffman's transformation into the character of Dorothy Michaels in the 1982 movie Tootsie is nothing short of remarkable. Struggling to find a job as an actor because of his difficult personality, he decides to dress as a woman to audition for the same role he was denied. Once he takes on the voice and persona of Dorothy, he fully embodies the character, bringing her nuanced struggles as a woman in a male-dominated acting world to the forefront.

While some may have thought this portrayal would perpetuate stereotypes or diminish female struggles, Hoffman saw it as a way to call attention to the injustices women face in the entertainment industry. Despite the controversies, Tootsie remains a classic, and Hoffman's performance as Dorothy is still regarded as one of his greatest achievements.

The tough-talking, gun-toting elderly woman has become an iconic figure in pop culture thanks to the creative genius of Tyler Perry. As a playwright, actor, and filmmaker, Perry has won over audiences of all backgrounds with his unique and memorable character. Madea is famous for her no-nonsense attitude and ability to dispense tough love and advice, usually with a healthy dose of humor.

Though some have criticized Perry for perpetuating negative stereotypes of Black women, his fans can't get enough. In fact, Perry's portrayal of Madea has earned him numerous awards and accolades and a dedicated following that keeps growing.

Tim Curry's unforgettable performance as the mad scientist and alien Dr. Frank N. Furter will have you singing and dancing along. Known for his extravagant costumes and heavy makeup, Curry's portrayal of the iconic character has solidified his place in cinematic history as one of the most legendary drag performances ever.

Initially, The Rocky Horror Picture Show received mixed reviews from audiences and critics alike. While some praised the film's innovative blend of science fiction, horror, and musical theater, others found it confusing and off-putting. However, over time, the film has become a beloved cult classic, with audiences embracing its quirky humor, catchy songs, and gender-bending themes. The film's enduring popularity has inspired countless stage productions, tribute shows, and fan communities, cementing its place as one of the most influential and beloved films of all time.

Angelina Jolie's androgynous portrayal of the fierce CIA agent protagonist sparked a conversation about representation in Hollywood and challenged societal norms surrounding femininity and masculinity.

While some praised Jolie for portraying a powerful female lead, others criticized the lack of depth in her character's gender identity. Nonetheless, Jolie's performance remains a powerful reminder of the ongoing struggle for gender equality and representation in the entertainment industry.

Fun fact: Tom Cruise was originally supposed to star as the lead character in the film, but ended up bowing out because he felt "Edwin Salt" was too close to his Mission Impossible character.

Some Like It Hot will always be remembered as one of Hollywood's most iconic films, and Tony Curtis's portrayal of Joe/Josephine is a big reason why. Playing opposite Jack Lemmon's unforgettable Daphne, Curtis's character serves up a seriously side-splitting performance as a smooth-talking ladies' man who finds himself in the most unexpected of situations. Watching him navigate his way through a group of talented female musicians while trying to keep his true identity a secret is pure comedic gold, and it's no wonder this film continues to be celebrated as a true Hollywood classic.

Like Lemmon, Curtis' decision to dress in drag was initially met with some resistance from the film's producers, but it ultimately contributed to the film's enduring popularity and cemented both actors' legacies as comedic icons.

Cameron Diaz, Lucy Lui, and Drew Barrymore were among the hottest women working in Hollywood when the 2000 film adaptation of Charlie’s Angels was released. The film was a huge success and was followed by a sequel that was not quite as successful.

In one scene, two of the Angels played by Drew Barrymore and Cameron Diaz go undercover as men and still somehow look great doing it. It may not have been the best adaptation of the iconic television series but it was still a fun ride and the three leads really showed audiences their range.

Lady Gaga performed at the 2011 Video Music Awards in a way most people didn’t expect. Gaga dressed in her drag king persona Jo Calderone for a new rock-flavored rendition of her single "You and I" from the album Born This Way by Interscope Records.

Brian May of the legendary band Queen made an appearance mid-way through her performance. For music fans, it was a dream come true and one of Lady Gaga’s…ahem…Jo Calderone’s most memorable performances to-date. And the crew of backup greaser dudes behind her was just the cherry on top.

Cillian Murphy dressed in drag for the comedy-drama film Breakfast on Pluto, about a transgender foundling searching for her long-lost mother in Ireland while also working as a sex worker and cabaret performer. The film explores the daily struggles faced by the LGBTQ+ community, particularly at a time with even less acceptance than now.

Among the array of chameleon performances, Cillian Murphy shines in his role as Kitten. The unique film touches on some sensitive topics and provides some insightful social commentary that remains relevant to this very day. It’s a performance that should not be missed by any means!

The Adventures of Priscilla, Queen of the Desert is a story about two drag queens played by Hugo Weaving and Guy Pierce and a transgender woman played by Terrence Stamp who venture through the Australian Outback on a tour bus meeting an array of interesting characters along the way.

The unique road trip film was praised for its positive portrayal of the LGBT community and even won an Academy Award for Best Costume Design. Terrence Stamp gives an amazing performance as the trans character and honestly should have gotten an Oscar for it too.

Chris Tucker played this simultaneously hilarious but annoying iconic character, Ruby Rhod in The Fifth Element. And the drag Tucker wears is just one part of the performance that makes his role so memorable. The DJ character was loud, obnoxious, and often seemed totally out of place.

Nonetheless, Tucker stole the show in just about every scene he was in. He provided a strong contrast against Bruce Willis’s strong, silent demeanor – you know the one he has for just about every film he’s in. The film became a cult classic and its easy to see why Ruby Rhod is one of its most referenced characters.

Amanda Bynes starred in this comedy sports film that was a light adaptation of William Shakespeare’s Twelfth Night. And in true Shakespearean tradition, it features someone in drag. Amanda Bynes plays a teenage girl, Viola Hastings, who pretends to be a boy in order to play on a boy’s soccer team.

Amanda Bynes is absolutely lovable in her role as Viola and we can’t think of anyone more suitable for the slapstick comedy role more than her. Channing Tatum, who also stars in the film, too, makes the film worth revisiting if you haven’t seen it in a while.

Marlon and Shawn Wayans starred in this light remake of Some Like It Hot for the modern age, dressing not only in drag but posing as white as well. Disturbing in the most hilarious way, Marlon and Shawn Wayans make this film worth watching at least once.

The IRL brothers play two FBI agents who go undercover as white women in order to stop a kidnapping plot against two hotel heiresses. While the film was nominated for multiple Golden Raspberry awards and panned by critics, it was a box office success earning a whopping $113.1 million worldwide, well over what it cost to make the film.

For Boondock Saints, Willem Dafoe played Duce, an undercover agent who ends up posing as a female prostitute in this one scene. The FBI agent later chases down the two brothers the film centers around who are carrying out vigilante justice, and ultimately ends up helping them.

Dafoe's performance is nuanced and complex, bringing depth to a character who is struggling with his own beliefs and values. In a film where really violence is the whole point, Dafoe gives a standout performance that puts him leagues above his co-stars.

Kurt Russell played in this buddy cop film Tango & Cash, playing two LAPD narcotics detectives who are framed for murder. In one scene, Kurt Russell is dressed as a woman in order to escape a night club that is surrounded by cops.

Kurt Russell delivers a fun and entertaining performance in "Tango & Cash," bringing his trademark charisma and subtle humor to the role. He and Sylvester Stallone, who also gives a great performance in his role, have excellent chemistry together. It’s a must-see film if you have an appreciation for buddy cop films.

Neil Patrick Harris dressed in drag for this musical about a transgender singer of a fictional rock band. Based on a book by John Cameron Mitchell, the story was turned into a musical in 1998, with the title role having been originally played John Cameron Mitchell.

Neil Patrick Harris took on the titular role in 2014, giving a tour de force performance. Harris delivers a ranged performance with astounding energy like no one else. Offering his talented singing voice and versatility to the role, his performance captivated audiences and earned him a Tony Award win.

It’s not too often you get to see Johnny Depp in drag but when you do, it’s glorious. For the 2000 film, Before Night Falls, a film that stars a young Javier Bardem, Johnny Depp has a small, standout role as Bon Bon, a drag queen in the film about a gay Cuban poet.

It was certainly a different role for Depp at the time who usually played masculine characters, and was quite the sex symbol. Interestingly, that wasn’t his only role in the film. Depp also plays Lt. Victor in the film, an evil prison warden.

Hilary Swank gained massive attention for her breakout role in Boy’s Don’t Cry, about a trans man who falls victim to a hate crime in Nebraska. The film underwent a three-year-long casting process before Hilary Swank was ultimately chosen for the role. And boy, was the search worth it.

Hilary Swank gives an amazing performance in the starring role, showing rare talent that really comes up only once a generation. The talent she showed in the role got her numerous roles thereafter until she became a household name.  

I’m Not There was an unusual film for a lot of reasons. It was an autobiographical biopic about Bob Dylan and his various public personas but no one in the movie was even named Bob Dylan, including Cate Blanchett’s character Jude Quin who essentially was Bob Dylan’s electric rock phase during the ‘60s.

Playing the complex music icon couldn’t have been easy, but Cate Blanchett really stole the show in the film, capturing Dylan’s persona flawlessly. She even earned an Academy Award Best Supporting Actress nomination for her role.

It’s also worth noting the movie contained one of the last performances of the late Heath Ledger.

Martin Lawrence got in drag for the comedy film Big Momma’s House, playing an FBI agent tracking an escaped convict. His character goes undercover as an estranged grandmother of a former girlfriend. The film was a box office success and led to two sequels despite the fact that the original was panned by critics.

Martin Lawrence, nonetheless, delivered comedy gold. While at time the film can be tedious, some jokes really help the film take off even though they teeter on the silly side. It’s worth seeing once, and then never seeing again, but maybe have a drink – or two – beforehand.

Of course, the funny and talented, legendary silent film star Charlie Chaplin dressed in drag for short film A Busy Day. In it, he plays a wife who becomes jealous at her husband’s wandering eye at a military parade. This was the first of three films where Chaplin played a woman with the others being The Masquerader (1914) and A Woman (1915).

Charlie Chaplin’s energetic performance is enjoyable - to a degree but it’s certainly not one of his best films. The subject matter is dated, and the themes are overtly sexist, with Chaplin’s suffragette character being portrayed in a belligerent and villainous manner. Nevertheless, if you enjoy the history of film and Chaplin, you may find it worth watching.