When we were little, we did a lot of things that we look back on now and say to our younger selves “What were you thinking?” A lot of our parents have those cute little embarrassing pictures of us in cowboy suits, wearing a tutu, or trying on mommy’s heels. Mom thinks they’re adorable and we want to burn every photo that exists. You didn’t know any better, so you can’t fault yourself. But those pictures definitely come back to haunt you, especially when mom gets comfortable with your new girlfriend or boyfriend. Oh, mom. Really?
To be quite honest, we were cross-dressing before we knew what we were doing. All we were doing was having fun. Nowadays, a lot of people have different opinions of people that wear clothing options of the opposite sex. Men dressing as women and women dressing as men has started to become a part of the norm and when some people see their favorite celebrities switching gender apparel, they think it’s cool and start to do the same.
In actuality, it’s starting to gain more and more momentum through fashion and celebrities. More celebrities are beginning to cross genders in movies and television. Maybe it’s to keep up with the times, or maybe it’s to gain more money playing double parts. We don’t really know. But we do know that it happens and we’ve compiled a list of some big names that have gone from hunk to chic and vice versa.
15 Tyler Perry – Madea
First on our list of cross dressers is actor and producer Tyler Perry. Perry gained notoriety through his Madea character over the years and doesn’t seem to be retiring the character anytime soon. Beginning in 1999 with the play turned movie I Can Do Bad All By Myself, Tyler Perry’s Madea came to life as an old, loud criminal of a woman whose mischief has ranged from deadly weapons to running from the law. Madea films are often used to teach lessons about friends and family, with Madea being the center of most situations. The reception of Madea has been both good and bad. The most critical reception comes from fellow African-American producer Spike Lee who believes that Madea represents “coonery and buffoonery.” Perry has responded to Lee’s consistent criticism saying that he needs to “shut the hell up” because he’s had problems with everyone from Oprah Winfrey to Clint Eastwood.
14 Jared Leto – Dallas Buyer’s Club
Actor Jared Leto starred as transgender woman Rayon in the 2013 film Dallas Buyer’s Club alongside Matthew McConaughey. The film tells the story of a man diagnosed with AIDS that goes on the journey to find and distribute drugs to help with the disease that had been under-researched. For the role, Leto stated that he lost 30 pounds, shaved his entire body, and met with actual transgender people that had contracted HIV/AIDS to get more information for his role. It was also stated that he never broke character while on set on and off camera. He said the role of Rayon was the “role of a lifetime,” “an incredible opportunity,” and “one of the greatest things” he had ever done. The role came as Leto’s first role after his acting hiatus of almost six years and he almost missed out because of his music. The role won Leto an Oscar, his first, for Best Supporting Actor in 2013.
13 Hilary Swank – Boys Don’t Cry
In one of the more notable performances of her career, actress Hilary Swank portrayed transgender Brandon Teena in the 1999 film Boy’s Don’t Cry. The film was based on the true story of Teena who was raped and killed for being a transgender man. Hilary Swank admits that she lied about her age for the role, but got the part after portraying Brandon Teena exactly as the directors expected. Swank says that she lived as a guy for a few months in preparation for filming. She stuffed her pants, worked out to bulk up, and taped her breasts down. She also said that it was sometimes hard to break out of her role and that when days came and they weren’t filming she never thought she’d be able to go back to her normal self. It took her two weeks of alone time with family and friends to break out of the character’s life and back into her own.
12 Channing Tatum – Lip Sync Battle
In a little mood lightener, hunky actor and dancer Channing Tatum channeled his inner Beyoncé in a round of Lip Sync Battle versus his wife Jenna Dewan-Tatum. In the second round, Jenna came out dressed in Tatum’s Magic Mike character’s attire and did a routine to the classic Ginuwine song "Pony." In response, Tatum came out in full Bey wear and performed her song “Who Run The World (Girls).” During his performance, none other than Queen Bey herself stepped out and joined in. To make it even more surprising, the backstage crew made sure that Beyonce and Tatum didn’t run across each other making their time onstage together the first time that they had actually met each other. Even though the encounter didn’t last long, Tatum was just as star struck as everyone else, but didn’t break character. Reports say that Tatum sent Bey a video message asking her to come to the show and she obliged.
11 Tom Holland- Lip Sync Battle
Another notable Lip Sync Battle performance comes from young actor turned Spider-Man Tom Holland. Holland plays the latest rendition of Spider-Man in this year’s Spider-Man: Homecoming (really, how many more Spider-Man stories do we need?) On Lip Sync Battle, Holland comes out “Singin’ in the Rain” tap dancing complete with a three-piece suit and an umbrella. The real magic begins when Holland channels his inner Rihanna and leaves it all on the stage, literally. His performance came with dancing, rain, and umbrella magic. His competitor Zendaya’s Bruno Mars performance didn’t stand a chance against his dancing skills coupled with a wig that didn’t budge and a corset that probably only Rihanna herself could pull off. If you didn’t know Tom Holland before, you definitely knew him after that because it was all anyone was talking about for a while.
10 Amanda Bynes - She’s The Man
In this 2006 film, Amanda Bynes plays the role of Viola and Sebastian, Viola’s twin brother. After Sebastian secretly sneaks away to London and asks Viola to cover for him, Viola ends up portraying her brother at his school in order to join the soccer team to show up her ex-boyfriend. The whole backstory is weird, as well as the movie itself. She ends up falling for a guy who’s on the soccer team whose girlfriend ends up falling for Sebastian. It gets even weirder when the real Sebastian comes back to town. It’s confusing to say the least and it also didn’t do the best in theaters, but for some reason people love it. To prepare for her role, she tried to mimic the mannerisms of real men on the street and observe how both men and women acted in public. The film was also supposedly inspired by William Shakespeare’s Twelfth Night.
9 Eddie Murphy - Nutty Professor
Ah, The Nutty Professor. Who can forget Sherman Klump and his evil alter ego Buddy Love? Eddie Murphy plays 90% of the actors in this movie, showing just how versatile he is as an actor. His drag appearance comes in the shapes of Mama and Grandma Klump. As Mama Klump, he adds a fat suit to his wardrobe to give the obese appearance like Sherman but as the grandmother, Murphy only adds the feminine clothes and wig. Nutty Professor is based on a 1963 Jerry Lewis comedy by the same name, and Lewis rightfully served as an executive producer. He regretted helping with the film because it ruined his film’s perfection and he also turned down a cameo because it had too many fart jokes. The film has won Murphy an Academy Award for Best Makeup and grossed $274 million opposed to its $54 million budget.
8 Adam Sandler – Jack and Jill
In Adam Sandler’s self-produced 2011 film Jack and Jill, he portrays Jack… and Jill, Jack’s twin sister. In this quirky comedy, Jack and Jill are identical twins who are anything but alike. Jack is smart and successful, and Jill never left their hometown and didn’t do much with herself. Thanksgiving is coming up and Jack regrets spending time with his sister because she’s embarrassing. Long story short, they get closer through the help of fellow actors Katie Holmes, Al Pacino, and David Spade. Apparently this film super sucked and was nominated for ten Razzie awards, which it won all of including Worst Picture and Worst Director. Yikes. It received a rating of 3% on Rotten Tomatoes and has been called the worst movie ever made on more than one occasion. It’s easy to say this is one of Adam Sandler’s movies that should’ve just stayed a thought in his head.
7 Glenn Close – Albert Nobbs
Glenn Close stars as the main character, which the film is named after, in this 2011 drama. Albert Nobbs is a butler with a secret: he’s really a she. He tries to raise money to have his own business and meets a few characters along the way including a hotel painter Hubert Page (Janet McTeer), who is also living the life of a man but was born a woman. Page and Nobbs begin a friendship along with Hubert’s “wife” Cathleen who helps him live his lie. The film didn’t do so hot in the box office, bringing in only slightly more than its budget. Glenn Close, who also serves as a producer, stated that she cried when she saw herself as a man for the first time. She and her husband, along with a few friends, raised the money for the movie and hoped it would be revolutionary. It didn’t appear to end up that way.
6 Woody Harrelson - Anger Management
In the 2003 film Anger Management starring Adam Sandler and Jack Nicholson, Woody Harrelson played a small, but hilarious role as transvestite prostitute Galaxia. Nicholson stars as Buddy, Sandler’s anger management coach. Sandler’s character Dave and Buddy had an altercation on a plane that led to the anger management classes and Buddy’s weird ways of dealing with anger. During one of their gatherings, Dave had an encounter with Harrelson’s character Galaxia that was supposed to help his anger issues towards gay people. I’m almost certain it didn’t work. Galaxia slaps him up a few times before the encounter only furthering his anger. The movie itself ended up being an average film with average ratings that did pretty okay in the box office. It was the first film of Harrelson’s after a four-year hiatus from 1999 to the film’s 2003 release.
5 Shawn and Marlon Wayans – White Chicks
Not only did Shawn and Marlon Wayans go drag, they also went white-face. Black FBI agents and brothers Marcus and Kevin Copeland ruin a drug bust in the beginning of the movie and get stuck with babysitting duty for a couple of rich socialites. After a car accident bruises the girls, and the brothers’ attempts to get back good with the chief, they decide to portray the women during their weekend in the Hamptons. This movie is wrong on so many levels, but you have to admit it’s funny. First off, the white-face thing is just… bad. But when it comes to the Wayans, you never really know what you’re going to get. The film was nominated for a few Razzie awards including Worst Picture and Worst Actress, but failed to take home the awards which in this case isn’t a bad thing. Also, Terry Crews singing “A Thousand Miles” is iconic.
4 Patrick Stewart – Blunt Talk, Season 2
X-Men’s leading man Patrick Stewart is one of the more versatile actors in the game right now, and his range got a little further when he showed up dressed in drag at an event for the second season premiere of his Starz sitcom Blunt Talk. Dressed in a pink dress, face full of makeup, and a blonde wig, he’s been said to resemble actresses Cate Blanchett and Helen Mirren. Stewart said that he loved the show because it made him do a lot of things that he had never done before, like dress in drag for example. The show was about a newscaster that made it his goal to make it big. Well, so much for those dreams because the show was cancelled after season 2. Recently the picture resurfaced and he’s been said to resemble Trump Counselor Kellyanne Conway. There’s even been an attempt for him to portray her on SNL alongside Alec Baldwin as Donald Trump. What a sight.
3 Ving Rhames - Holiday Heart
So…here’s one person that I never thought I would see doing drag. Honestly, Ving Rhames as a woman just gives me nightmares. Ving Rhames plays Holiday in Showtime movie Holiday Heart. He’s a homosexual drag queen that has a strong dedication to his religion. He takes in a drug addict and her daughter and raises the daughter as if she was his own. Trials and tribulations continue throughout the movie, which is actually pretty sad. But I can’t get past Holiday’s high voice and bright colored attire. I never took this movie seriously because, come on, Ving Rhames could literally knock you out by just looking at you. Surprisingly though, you don’t think he’s any less of a man by doing the role, he’s just a guy dressed like a woman that sounds like a woman that can punch really hard.
2 John Travolta - Hairspray
This one didn’t surprise me as much; John Travolta played Tracy’s mom Edna Turnblad in the 2007 rendition of Hairspray. The film followed a long line of previous releases including a Broadway musical version. Travolta is no stranger to musicals, so the role wasn’t too far-fetched with the exception of heels and a dress. Travolta stated that he had to sit for five hours getting the makeup transformation and he also had to wear a 30-pound tight fitting bodysuit. Executives of the movie company wanted someone who had done drag before such as Steve Martin or Robin Williams, but producers had their eyes set on Travolta due to his performance in Grease. Who doesn’t love Grease? Besides, the producers got the right idea because the star-studded cast including Michelle Pfeiffer and Christopher Walken grossed for $202 million and received three Golden Globe nominations.
1 Robin Williams – Mrs. Doubtfire
Last, but not least on our list is Robin Williams playing the role of Mrs. Doubtfire. In this 1993 film, Williams plays Daniel, a voice actor who loves his kids. After he and his wife get a divorce, his now ex-wife looks for a nanny and he responds as Mrs. Doubtfire and gets the job to be close to his kids. Lessons are taught and the kids fall in love with him before finding out who he really is. His true identity comes to fruition and his ex-wife ends up getting full custody of the kids. Eventually, she grants him partial custody and everything is right with the world. Robin Williams was a great actor that changed many lives with his films including Aladdin and Good Will Hunting. Unfortunately, his life was cut short after he committed suicide in 2014, due to a form of dementia according to his wife. His death affected many and the comedic acting world won’t be the same without him.
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