Hollywood has always had an obsession with appearances and apparel, whether it’s the “Who are you wearing?” questions on the red carpet or who gets offered the most lucrative brand endorsement deals. Apparel is not only a portion of a celebrity’s identity on the red carpet, but also an important aspect of creating a character on film.
Since people tend to use their choices in fashion as a way to express themselves, they don’t always conform to the boundaries set by gender stereotypes. Diane Keaton is one example of a celebrity that doesn’t adhere to gender-specific clothing, and has become famous for her love affair with pant suits, blazers, and men’s ties. Even Angelina Jolie recently walked the red carpet wearing matching suits with Brad Pitt.
However, not everyone has the same relaxed notions behind dressing as the opposite sex. Dave Chapelle famously had an interview with Oprah Winfrey where he discussed a previous experience he had while filming a movie with Martin Lawrence. He reflected on a possible correlation between emasculation and African American comedians in Hollywood. When he discussed his refusal to wear the dress they were requesting, he said “you gotta take a stand.”
Yet, one actor’s conspiracy theory is another actor’s go-to stunt. Whether you find it offensive, effeminate, or hilariously funny, there are a surprising number of celebrities that have cross-dressed both on and off the screen. Check out our list of 15 celebs that have cross-dressed, and see which of your favorite stars have dabbled in dressing as the opposite sex.
15 Chris Hemsworth
When Aussie brothers Chris and Liam Hemsworth were first introduced to audiences, people were surprised at how much talent could be in one family. Chris’s success in the Marvel film series and Liam’s success in The Hunger Games film series let audiences know they weren’t just a fleeting flash in the pan in Hollywood. While Chris was respected in the industry, not much more was known about him other than his brother was dating Miley Cyrus. It was his appearance on SNL in December 2015 that really showed a different side of Chris Hemsworth. During a skit involving a bunch of ladies brunching, Chris plays himself dressed as a woman to try and sneak information about whether or not the ladies think he’s a hot leading man. The ladies call him out once he explodes at the thought that his brother is the better looking actor. The result is comedy genius, and fans got to see what Thor would look like as a woman.
14 Kristin Davis
Kristin Davis is best known for her portrayal of Charlotte Goldenblatt from the HBO series, Sex and the City, which later resulted into two separate films. While the plot-line of the series revolves around the many different sexual escapades of its characters, Samantha’s character is usually the first that comes to mind when it comes to provocative scenes. However, in Season four of the show, Kristin’s character is dressed up in drag to be photographed as a man. While she initially felt timid, the scene went on to show an empowered Charlotte asking for “a bigger sock.” In the end, audiences got to see how the picture turned out, and the consensus was she looked pretty good as a man.
13 Jim Parsons
Jim Parsons isn’t new to having difficulties when portraying a specific character. Portraying the genius Sheldon Cooper on The Big Bang Theory, he has to memorize complicated scientific lingo with each episode. However, it was in the fifth season of the show, where he walks into the cafeteria wearing a French maid's costume in the episode, “The Hawking Excitation,” that showed his true devotion to his craft. During an interview with Conan O’Brien, Parsons divulged that when he was initially approached about the episode, they were asking for him to wear the Princess Leia slave bikini costume. After he expressed concerns that he didn’t feel comfortable with it, they downgraded it to a French maid’s costume. We’re not quite sure which one is worse, but the Princess Leia would have definitely shown more skin.
12 Dennis Rodman
Despite being an athlete respected for his skill on the court, much of his fame came from his flamboyant tendencies off the court. From the multicolored hair to the occasional appearances wearing red lipstick, he always followed the beat of his own drum. However, it was the book release event for his best-selling biography that had people talking the most. Showing up in a wedding dress, veil, wig, and full makeup, Rodman announced he was marrying himself, and that he was bisexual. While many thought of it as a publicity trick (and an alleged payment from the designer of the dress to wear it in public), this wasn’t the only time Rodman was photographed wearing women’s clothing.
11 Justin Timberlake
Justin Timberlake is known for his ability to excel at late night talk shows, and anything with a comedic skit. The “History of Rap” skits he performs with Jimmy Fallon are hugely popular on the Internet, and he is a regular on SNL. There have been a few times that Justin has cross-dressed on popular television shows, but the most memorable involves him wearing a black leotard and high heel pumps dancing alongside Beyonce. Recreating the “Single Ladies” video, Justin is just another one of the background dancers, but seems to nail the moves perfectly. Just another one of Justin’s many skills: he can dance in heels.
10 Bruno Mars
When Bruno Mars was asked on SNL in 2012, he wasn’t asked solely as a performer. Hosting SNL is quite a different experience, since it involves being the headline attraction for the episode. From the monologue to the numerous skits, Bruno Mars proved he could play a variety of different characters. However, it was his portrayal of “Melody” in one of the skits that showed he wasn’t afraid to think outside of the box to get a few laughs. From a pony-tailed wig to twerking in a skirt, Bruno didn’t get hung up on the logistics of the skit and totally went for it. The result was an even bigger fascination with the music artist, and probably helped him land the deal to perform at his first Super Bowl Halftime Show.
9 Lady Gaga
Lady Gaga has always tried to push the envelope when it comes to expressing herself as an artist. Meat dresses, blood splattering, and over-the-top headpieces became the norm when people saw Lady Gaga at an awards show. So, when people saw her dressed as a man, they didn’t exactly know what to think. She first released the look on Twitter through the album cover for “You and I,” and then she gave that alter ego a name at the 2011 MTV VMAs. “Joe Calderone” was a cigarette-smoking, dirty kind of guy, and Gaga never broke character throughout the event. “Joe” can even be seen giving a congratulatory nod towards Jay Z after Beyonce showed off her newly pregnant belly during her VMA performance.
8 Shawn & Marlon Wayans
If two white cops dressed up as two black girls during an undercover assignment, the result wouldn’t be a hugely recognizable comedy. However, when Shawn and Marlon Wayans donned “white face” in the film, White Chicks, no one seemed to bat an eye. Instead, the film has a bit of a cult following, and even recently made headlines in a Twitter war. Snoop Dogg made a comment about Iggy Azalea looking like one of the characters from the White Chicks film, and she responded by dressing up like them for Halloween in 2014. While no one seemed to want to get into that debate, the world couldn’t help but notice how easily she was able to transform into the character without too much of a costume.
7 Tom Hanks
While many A-list actors have come from television, oftentimes they try to distance themselves from the roles they were forced to take when they were struggling to make it onto the big screen. From Demi Moore starting off in soap operas to Will Smith in The Fresh Prince of Bel-Air, it’s not so unheard of for an actor to have humble beginnings. However, Tom Hanks seems to have the funniest television origin, since he once played a cross-dresser in the television series, Bosom Buddies. While the lovable Tom Hanks is the only actor that could still make it to Hollywood’s A-list after such a ridiculous show, the series was canceled after two seasons and we have yet to see him in drag ever since.
6 Channing Tatum
Channing Tatum might be best known for his sexy role as “Magic Mike,” but recently he has shown that he’s not afraid to shed his heartthrob persona. During a performance on Spike’s Lip Sync Battle, Channing Tatum chose Beyonce’s “Run The World,” and went all out. Channing wore a wig (that looked surprisingly real), and a full Beyonce-esque outfit complete with boots. He also made an appearance on Jimmy Fallon’s “Ew!” skit, and showed up as “Susie Callahan.” Channing had a brown wig and yellow dress with a matching headband to complete the overall look. “Suzie” began dancing, and it was definitely a change from the Magic Mike dancing we’re used to from Channing Tatum.
5 Jimmy Fallon
Jimmy Fallon is known for his popular skits on The Tonight Show Starring Jimmy Fallon. Jay Leno even praised his ability as a young man, referencing the popular rapping and dancing skits Fallon performs with Justin Timberlake. While fans didn’t think it could get any better than his Lip Sync Battles, Fallon came out with a brand new skit called, “Ew!” Fallon plays a young girl named, Sara, that is hosting her own talk show and often invites over her “friends.” Fallon dons a blonde wig, braces, and a ruffled purple dress. The skit has become hugely popular and he’s had a number of different celebrity guests on like Zac Efron and Seth Rogen (all in drag).
4 Eddie Murphy
Eddie Murphy has played in a number of iconic films throughout his professional career. From Coming To America to the Beverly Hills Cop film series, there isn’t any doubt that he can play a variety of different characters. However, it was The Nutty Professor film series that really proved that he could do it all. Playing multiple characters in each film, he showed prosthetics, makeup, and costume can help to create a completely different persona on-screen. The mother figure in The Nutty Professor seemed to be the most memorable, and to this day people still quote the infamous line in the film where she claps her hands and declares, “Hercules, Hercules, Hercules!”
3 Jamie Foxx
In Living Color was a show that spawned a number of our favorite celebrities in film and music. J. Lo used to be a Fly Girl, and Jim Carrey and Jamie Foxx were regulars performing hilarious skits. However, it was Jamie Foxx’s portrayal as Wanda Wayne that proved he was willing to take his craft to the next level as a comedian. Crossing his eyes, puckering his lips, and donning an absurd blonde and curly wig, it’s hard to believe that this was the origin for the Academy Award winning actor that breathed new life into Ray Charles with his performance in Ray.
2 Martin Lawrence
When the hugely popular television series, Martin, finally came to an end, fans thought they would never again see their favorite character, Shananay, played by comedian Martin Lawrence. Playing the over-the-top female character, Martin showed he could embody the character of the ugliest woman in the world and still make us laugh at the same time. Rather than shedding his former drag television past, he carried on this tradition when he transitioned into film. Playing in the hugely popular Big Momma’s House film series, Martin Lawrence proved he could play a woman ranging from young and ghetto to old and fat.
1 Tyler Perry
Although James Brown may be known as “The Hardest Working Man in Show Business,” Tyler Perry is definitely giving him a run for his money. Actor, producer, director, screenwriter, playwright, and all around Jack of all trade, Tyler Perry’s biggest recognition comes from the character he created after the success of his first debut play. Madea has such character and distinct personality that it can be easy for the audience to forget that she’s just Tyler Perry in drag. Depicted on film and on the Broadway stage, Tyler Perry has made quite a pretty penny portraying the elderly Mabel “Madea” Simmons.