Women: the most mysterious creatures in the universe, more mysterious than the universe itself. Well, at least to us dudes, anyway. We can’t quite wrap our minds around how exactly their minds are wrapped. It’s like they’re a totally different gender or something, like their initial chromosome is the dual opposite of ours.
We can attempt to imagine how women imagine us, and, really, we doubt they see us as much more than mostly-capable sausage brains. They wouldn’t be entirely wrong, though we’re hoping that they emphasize the “capable” part.
Whether it’s a man playing a woman or a woman playing a man, immersing oneself in a character of the opposite gender sounds like a great way to put a toe forward in understanding the other side of our duality. When actors play gender-transitioning roles, they’re contributing content to the totality of our understanding of gender itself (which, right now, is probably in its late infancy), and, in effect, our understanding of our own humanity. At least, that’s what happens when the actors do it well. Any lady can strut about a movie set with a sock in her pants, and any dude can put make-up on and go talk some gossip at a salon. Crude examples, we know, but we’re talking about crude portrayals here.
Here’s a few actors who played the opposite gender, to varying degrees of success.
16 The Wayans Bros. - White Chicks
This is a 2-for-1 crossdressing special. The famed (at least, they were famed back then) Wayans brothers cracked their high heels over pop culture back in 2004, when they donned whiteface and dolled themselves up in White Chicks.
A real alternative take on the classic American buddy cop comedy film, the Wayans brothers play FBI agents Kevin Copeland and Marcus Copeland. When they fail in their attempts to bust a criminal organization that sells drugs inside boxes of ice cream, their supervisor gives them one last chance to keep being FBI agents. Their mission? Protect billionaire cruise line heiresses Brittany and Tiffany Wilson, who are in town for a beauty competition. As fate would have it, the girls get into a car accident and receive extremely minor facial blemishes. The almost non-existent deformations are enough to keep the girls resolutely hermitted in their hotel rooms, leaving the Copeland brothers no choice but to disguise themselves as the two white chicks. Classic buddy cop shenanigans ensue.
15 Adam Sandler - Jack and Jill
Oh, Mr. Adam Sandler… what on Earth happened here? Didn’t any one of the hundreds of people working on this film happen to mention to you that this was a bad idea? They did, didn’t they? But you didn’t listen to them, didn’t you?
No, he didn’t. Against all rationality and good career choices, Sandler opted to play both Jack and Jill in 2011’s overwhelmingly cruddy Jack and Jill. The film is essentially Adam Sandler being extremely bland as Jack and extremely annoying as Jill. Jack and Jill go to Thanksgiving, Jack and Jill go to The Price Is Right, Jill tries online dating, Jack and Jill go to a Lakers game.
It pains us to speak ill of such an awesome childhood icon, and in the end, Sandler’s accomplishments as an actor far outweigh his recent unfortunate film choices. But none of that can sweeten the smell of the tremendous pile of turd Jack and Jill sits on.
14 Willem Dafoe - The Boondock Saints
Willem Dafoe, best known for playing the Green Goblin in Spider-Man and having a genuine trollface in real life, played an interesting role in 1999’s cult classic, The Boondock Saints. Despite having a production laden with issues which led to a limited release, the film was very successful as a home video product, and was eventually accepted by audiences as a niche pearl.
After fraternal twins Connor and Murphy MacManus kill two members of the Russian Mafia in self-defense, and later receive an apparent message from God telling them that they need to become vigilantes and sweep Boston of its evil men, FBI agent Paul Smecker (Willem Dafoe) does everything he can to stop them. That is, until he realizes he should probably be helping them instead. The film’s iconic drag scene features Dafoe as a fiery redhead who infiltrates the Russian mob’s headquarters and proceeds to shoot and kill a number of Russian soldiers.
13 Martin Lawrence - Big Momma’s House
Every time Martin Lawrence appears on screen, it’s like Christmas came early. But Christmas hasn’t come early for a long time, since Lawrence hasn’t acted in a film since 2011. His absence from the film industry is one of the many small reasons why Hollywood’s become a big smelly ash tray. At least we can go back and watch Big Momma’s House and feel like it’s Christmas morning all over again.
In the film, Lawrence plays FBI agent Malcolm Turner, undercover hero and master of disguise. Sent on a mission to capture deadly criminal Lester Vesco (played by a young Terrence Howard), Turner is led, through a series of events, to disguise himself as “Big Momma,” an elderly, heavyset bundle of joy.
It’s one of those movies that Rotten Tomatoes rolls its eyes at, but everyone else with a pulse tends to enjoy more and more with each viewing. Look out for Lawrence’s glorious comeback next year, in Bad Boys III.
12 Jared Leto - Dallas Buyers Club
Versatility seems to be a trademark among the few actors that have portrayed The Joker on screen, and Jared Leto, recent inductee into the very private club, has no shortage of it. Amid a solid filmography that includes him getting the crud beat out of him by Edward Norton in Fight Club (yeah go rewatch it, he played Angel Face), Leto wowed audiences worldwide with his performance as transgender woman Rayon in 2013’s Dallas Buyer’s Club.
In the film, Rayon serves as a sort of loopy, messed-up Jiminy Cricket to Ron Woodroof (Matthew McConaughey) as he falls down the deep, dark rabbit hole of AIDS. While the film stays mostly true to real life events, the character of Rayon was created as a composite, drawn-up from the writers’ interviews with transgender AIDS patients, as well as doctors and activists.
Leto was hauntingly brilliant in his portrayal of Rayon, earning a pile of awards for the role, including an Academy Award.
11 Ving Rames - Holiday Heart
Hey, Mr. Marsellus Wallace, what would your cronies think if they saw you dressed like that? Performing as a drag queen at a popular night club is a surefire way to lose your hold on an organized crime team that respects you and looks up to you in sheer horror.
Thankfully, Pulp Fiction is a piece of fiction; Marsellus Wallace and his thugs don’t technically exist, so actor Ving Rhames is free to dress up however he likes. So he dressed up as a full-out diva, playing Holiday Heart in 2000’s TV Movie, Holiday Heart.
It’s a TV movie, so the odds of it being good are slim. The plot has something to do with a homosexual black man helping out a recovering drug addict and her daughter. Sounds like a real yawn. Still, it might be worth checking out, if only to see ol' crazy Marsellus Wallace in drag.
9 Dustin Hoffman - Tootsie
1982’s Tootsie is an American comedy classic that tells the story of Michael Dorsey, a struggling actor whose bad reputation in Hollywood drives him to change his name to Dorothy Michaels, and try the movie game out as a woman. Michael Dorsey, as Dorothy Michaels, attained a level of media mania that he (she) could have never reached as a man. Hilarity ensues, along with shenanigans of all varieties.
The film was a Hollywood success in every possible sense. It earned 10 Academy Award nominations (though it only won one for Best Actress in a Supporting Role, awarded to Jessica Lange), was deemed in 1988 by the Library of Congress to be "culturally significant," currently holds an 89% rating on Rotten Tomatoes and, perhaps most impressive of all, was given a 4 out of 4 star rating by the late Roger Ebert, who called it a “Movie with a capital M.”
8 Fatty Arbuckle - Miss Fatty’s Seaside Lovers
Released in 1915, Miss Fatty’s Seaside Lovers is 11 minutes of ultra classic American comedy, and proof that a film doesn’t need something so fancy as dialogue to succeed as a piece of work.
The entirely silent film (with English intertitles) features Roscoe Conkling ‘Fatty’ Arbuckle as the lovely daughter of a wealthy mothball magnate. When the man and his family check into a hotel, all appears to be normal, except all of the men there can’t seem to take their eyes off the tycoon’s lovely daughter. To them, she is as timeless a beauty as has ever been seen before 1915. Classic hilarity ensues as the setting moves from a hotel to a beach, where the big damsel in distress is stranded on a rock. The hilarity peaks at the film’s end, during a classic, absurd rescue mission to save Miss Fatty from the rock. Definitely worth a watch if you’re into seeing Fatty in drag.
7 Eddie Murphy - The Nutty Professor, Norbit
Eddie Murphy has the kind of face that screams entertainment, no matter what gender he’s portraying. Of course, Mr. Murphy is more accustomed to gender versatility than most actors, having donned skirt and leggings for two different film roles (three if you count the sequel to The Nutty Professor, Nutty Professor II: The Klumps). Frankly, the man’s a master at it, exaggerating his female roles for maximum comedic effect, paying no mind to realism or other such absurdities.
Murphy played a whopping total of six roles in The Nutty Professor, two of them being female roles: Mama Anna Klump and Granny Klump. He does the same in the film’s sequel, not disappointing in any of the roles, in either of the films.
Norbit was definitely more on the disappointing side. In Norbit, aside from playing the titular character, Murphy plays his wife, Rasputia Latimore-Rice. He also plays the role of a super weird Chinese mutation, Mr. Wong. The man can do it all, even when he probably shouldn’t.
6 Cate Blanchett - I’m Not There
I’m Not There is a love letter to Bob Dylan in film form. Released in 2007 and starring a bevy of talented actors (among them Cate Blanchett, Christian Bale, Richard Gere and Heath Ledger), the film (a biographical musical drama) features six actors depicting different aspects of Bob Dylan’s persona.
Perhaps most interesting of these portrayals is Cate Blanchett’s, contrasting starkly with the other actors, being the only female playing Dylan. Blanchett plays one facet of Dylan named Jude Quinn, which is the name the film gives to electric guitar-era Dylan, who outraged a multitude of fans expecting and wanting folk music out of him.
Aside from being a well-made piece of film, I’m Not There is worth the watch, if not for the music and the unpacking of Bob Dylan’s psyche, then for the fact that it was the last film dear Heath Ledger had released in his lifetime.
5 Akihiro Miwa - Black Rose Mansion
Here’s a gender-defying film role from the far east to help cut through some of that Hollywood butter. Black Rose Mansion, directed by Kinji Fukasaku, is based on a play by Yukio Mishima. The film stars Akihiro Miwa as the film’s protagonist, Ryuko. We can’t imagine Miwa having a tremendous amount of difficulty adjusting to the role, given his real world distinction as a seasoned drag queen with long, flowing, shoulder-length bright yellow hair.
A strange and certainly perverse noir, Black Rose Mansion is the story of a hired singer named Black Rose, who begins working at an exclusive men’s health club. The owner of the club is thrown a series of curve balls as he realizes that his new entertainer is attracting a sling of her past lovers, all of whom happen to be homicidal.
Japanese film has its roots in traditional Kabuki theatre, which features men of all ages parading around as lavish female singers and dancers. This may imply that the idea of a man portraying a woman isn’t quite as abrasive in Japan as it is in the west.
4 Hugo Weaving - Cloud Atlas
Is that you, Agent Smith? Lord Elron - is that you, my lord? Why, yes it is.
Cloud Atlas, the Wachowskis’ epic effort at capturing transcendent grandiosity on film, is set across six different eras and areas, with each member of the main cast playing multiple roles. Here, Hugo Weaving, the undisputed duke of cinematic sci-fi and fantasy, plays the tenacious and abusive Nurse Noakes, who makes it her mission to keep 65-year-old publisher Timothy Cavendish locked inside a nursing home.
Weaving plays five other characters aside from Nurse Noakes. That’s asking a lot from an actor, and the Wackowskis asked the same from most of the main cast. The Matrix was cleaner (and better) but Cloud Atlas, if nothing else, was an enormous project to undertake. It reached for the stars. We happen to think it got quite far, though definitely not as far as the stars. Watch it if you haven’t already, and let us know how far you think it got.
3 Johnny Depp - Before Night Falls
Looking at Johnny Depp’s filmography, it would be absurd to think he hasn’t played a woman at some point. If Johnny Depp hasn’t played a woman, no one has. That’s the rule, and it’s one we respect, because other actors have portrayed women before, and Johnny Depp played the role of Bon Bon (as well as Lt. Victor) in the American drama film Before Night Falls.
Released in the year 2000, Before Night Falls is based on an autobiography of the same name written by Reinaldo Arenas, a Cuban novelist and poet. The film tells the story of Arenas, an openly gay man born in 1943, a time when being openly gay was anything but encouraged. Johnny Depp appears in the frame for a few good minutes, first playing a menacing prison warden, then a trans woman named Bon Bon. Check out the film and Depp’s role, see if you don’t find a few shades of Captain Jack Sparrow in it.
2 Cillian Murphy - Breakfast on Pluto
You may know him as Scarecrow in Batman Begins, or Robert Michael Fischer in Inception, where he was gracious enough to provide the mental landscape the majority of the film is set in. Before all that, however, Cillian Murphy was best known for his role as transgender foundling Patricia “Kitten” Braden in 2005’s Breakfast on Pluto.
The film follows Braden’s journey as she looks for love and her long-lost mother in small towns in London and Ireland in the 1970s. Murphy worked his butt off to prepare for the role. By “worked his butt off,” we mean he hung out with and took instructions from a bunch of drag queens, who took him out clubbing with them. He also deeply studied women’s body language which, admittedly, does seem more like hard work than clubbing. All his efforts ended up paying off; the role earned him a stream of award buzz which included a coveted Golden Globe nomination for Best Actor - Motion Picture Musical or Comedy.
1 Charlie Chaplin - A Woman
Released way back in 1915, Charlie Chaplin’s A Woman features Charlie Chaplin as a woman. Chaplin, like Mr. Eddie Murphy, is known as an actor who can do it all. In fact, he’s pretty much the first of his breed, and he set the example for all the all-doers who followed him. FYI, technically, there isn’t an actor alive who hasn’t followed Chaplin, in one way or another.
Running at 20 minutes and, like Fatty’s feature above, in complete silence (with English intertitles), A Woman follows the classically whimsical Chaplin as he meets and falls for a young lady in a park, who is there with her parents. Not wanting to be thwomped by the dad, Chaplin opts to get by him via disguise, dressing up as a woman.
This performance marked the final time Charlie Chaplin would portray a woman on film. He donned bra and nylons in two prior films: The Masquerader and A Busy Day.