10 Best Cross-Dressing Movies like She’s The Man

The classic boy-meets-girl film storyline gets jazzed up when one of them starts pretending to be a boy. So of course, that’s the girl pretending! And she ends up falling in love with the boy, but the boy thinks she is a girl! Oh, what a dilemma this is. And that’s what She’s The Man is all about… and soccer.

The 2006 comedy hit stars Amanda Bynes as Viola, a sporty teen whose soccer team got cut off before their school year started. She tried joining the boys’ team, but the coach didn’t want it. So she wanted to prove that girls could also compete with boys in soccer, and maybe end up being better.

The plan she thought of was to temporarily enroll in her twin brother’s new school. She pretends to be her twin, and gets in. She gets to play soccer, with the goal of competing against her own school’s soccer team. Confusing? Promise, this one is such a hoot to watch!

But this kind of gender-bender theme in movies is not new. Hollywood has a huge treasure chest of movies like She’s The Man. Some are comedies, some serious dramas. Check them out!

1. Some Like It Hot

Perhaps the mother – or father – of all these comedic gender-gender storylines is this 1959 film called Some Like It Hot.

The comedic film stars the voluptuous Marilyn Monroe as the lead singer of a traveling all-female band. But she’s not the one bending genders here. That would be her two co-stars, Tony Curtis and Jack Lemmon. The guys play two jazz players in a speakeasy bar that’s run by mobsters.

The story is set in the prohibition era of the late 1920s, and the film is shot in colorful black-and-white. When the two jazz guys accidentally saw a mobster-type killing, they feared for their lives and ran. They decided to join the traveling all-female band to escape town. And that’s where they meet Marilyn’s character named Kane.

But this is one of those movies like She’s The Man, so Kane meets the two guys disguised as girls! More comedy ensues when both guys try to compete for the affection of Kane, when they are not in disguise. Aw, just go watch this one because it’s just rowdy fun!

2. Shakespeare in Love

How about a gender-bending comedy of Shakespearean proportions? Then go watch this 1998 funny called Shakespeare in Love.

This is where Gwyneth Paltrow won an Academy Award for her performance of Viola, an upper class woman who cross-dresses as a man. Just her name alone, and her gender-bending of course, becomes a fine candidate for our list of movies like She’s The Man.

Now why the cross-dressing? Viola lives in the 1500s, at a time when William Shakespeare is struggling to get inspiration for writing new material. She’s a huge fan of his previous plays, and she wanted to try to act in one. So she decides to dress like a man to audition for his new play.

Now why did she dress like a man to audition? That’s because during Shakespeare’s time, no women are allowed to perform onstage. And the women roles were played by men who are dressed as a girl. Many speculate that this is where the term “drag” came from: Dressed As a Girl. Get it?

Go watch this superbly written material to see how their gender-bending staging plays out!

3. Connie and Carla

Funny enough, Connie and Carla is one of these movies like She’s The Man, but it’s also like Some Like It Hot. That’s because the story is about two women who cross-dress to escape mobsters. And yep, they also saw those mobsters murder someone. How about that?

This 2004 comedy stars Nia Vardalos and Toni Collette, the women who saw the mob rubout. They work as singers of show tunes musical revue performances. They ran to Los Angeles to hide there. And their hiding involves being gender-benders of a double kind: they dress up as men who are drag queens!

The two women’s musical revue background is just perfect since they auditioned for a slot in a local drag queen musical revue club. And they got an edge amongst the usually lip-syncing drag queens because they sang their songs live!

If you love Broadway tunes and wittily written funny lines, then go watch this one!

4. Switch

What about gender-bending with divine intervention? The 1991 comedy film Switch explores this storyline. And this is the reason why it’s also here in our list of movies like She’s The Man. This time, she is literally a man, trapped inside a woman’s body!

Let us explain further: There’s this very misogynistic man named Steve. During his lifetime, he has done many good deeds. The only problem is, he’s such a ladies man, and treats women like lower class citizens. He’s the wham-bam-thank-you-ma’am guy.

Steve dies, but he can’t go to heaven or hell directly. So he is made to undo his misogynistic mistake with women so that he could maybe enter heaven – or go to hell if he’s still hellish! Steve is reincarnated inside the body of a voluptuous female! And he names himself/herself as Amanda.

Watch this movie and see how a man literally experiences what it’s like to be a woman. It’s fun but also a good eye-opener for such kinds of men.

5. It’s A Boy Girl Thing

How about a film on equal opportunity gender-bending, meaning both the girl and boy switch places? This is what the film It’s A Boy Girl Thing explores.

The 2006 film is about two high school kids who are neighbors. Woody is one of those popular jocks in school while Nell is the nerdy and awkward type. Since they’re total opposites, they hate each other.

However, fate tries to test the two one day. They were assigned together to work on a school assignment, but they always end up fighting each other. One of these fights took place in a natural museum during a school field trip. An ancient Aztec statue was beside them when they fought – and some Aztec magic worked its powers on them.

So what happened? This is where you encounter the reason as to why it’s in our list of movies like She’s The Man. Nell, the she, becomes the man! Like literally! Meanwhile, he’s also the woman, as Woody wakes up inside the body of Nell.

Watch how this epic gender-bending comedy unravels this kind of complication and confusion in the lives of these characters!

6. Just One of the Guys

What about a gender-bending mission to debunk the gender working gap? Go watch Just One of the Guys for that, and see why it’s on this list of movies like She’s The Man.

Interestingly enough, this 1985 film tells the story of a young female student who wants to be a professional journalist. But her skills and talents seem to be lacking in this department, according to her teachers. However, she believes that they don’t take her seriously as a journalist because she’s a girl.

So what’s a girl got to do in a situation like this? Dress as a boy, of course! To prove her critics wrong, she dresses as a boy and enrolls in another school to become a student journalist there. Wanna see what happens next? Then watch this and find out!

7. Tootsie

Gender-bending to prove sporty skills is one thing. But gender-bending as a woman to get a job after being such a hard-headed man is another. That’s basically the plot for the classic 1982 film Tootsie.

The film stars the great Dustin Hoffman, playing an actor named Michael Dorsey. Since he’s so meticulous to a fault, the local film and movie industry people resent him. He finds himself without any kind of job, and slowly becoming desperate.

A popular TV soap opera held an audition for a female role, and Michael decided to try out for that. So he dressed as a woman and won the audition. Since he’s really such a good actor anyway, he wins over the cast and the audiences. Her female role in the TV program becomes a very popular icon.

And this is why it belongs to this list of movies like She’s The Man. Michael finds himself excelling in his work, much like Viola knew she would excel in her sports. This is indeed a classic you should not miss in your movie-viewing life. So go check it out!

8. Mrs. Doubtfire

How about gender-bending to be with your kids, because you’re such an unreliable father? That’s what the film Mrs. Doubtfire is all about.

The 1993 film stars the very talented Robin Williams as Daniel, a family man who shuffles to and fro, just to get acting jobs. Also a struggling actor, he finds himself prioritizing work over family sometimes. This is why his wife files for divorce. To make matters worse, he can’t have joint custody of their children because his work situation is so unstable.

So in order to be closer to them, he remedies the situation and finds small jobs. But there’s one big job that he saw, which interested him. It’s the job post for a nanny, put up by his ex-wife, to find a caretaker for their kids.

And this is where the story turns to become one of those films like She’s The Man. Daniel tries to use his acting skills and “auditions” for the nanny role. Of course he gets it. So he gets to have a better job while being close to his kids. Of course trouble begins when a new man in his ex-wife’s life suddenly comes into play.

What would Daniel, now known as nanny Mrs. Doubtfire, do with this situation? Watch and experience Robin Williams in one of his finest roles.

9. The Hot Chick

It’s one thing to role-play your gender-bending, and it’s another thing to switch bodies with the opposite gender of your age. But what about switching and bending with someone who’s a lot older or younger than you? Then we have The Hot Chick for you.

The 2002 film stars Rob Schneider, a small-time crook named Clive who’s a bungling type of criminal. Rachel McAdams co-starred as the teenage cheerleader Jessica who’s a bit mean-spirited. Their body-switching gender-bending episode comes in the form of stolen mystical jewels.

This is why The Hot Chick belongs in list of films like She’s The Man. As it turns out, a special pair of seemingly hexed earrings finds their way to our zany characters. Jessica, being her obnoxious self, tries to frame her teen rival for shoplifting in a mall. While there, she also steals the special earrings on display in a jewel store as an added mischievous act.

Stopping by for gas one time, the crook Clive is also there. He just did a scam there, but gets mistaken for a gasoline boy. In the process, Jessica accidentally drops one of the special earrings, and Clive spots it and steals it.

Arriving in their respective homes that night, both Jessica and Clive try to wear the earrings, at the same time. So the magic earrings makes the wearers switch bodies temporarily. And this is where trouble begins.

This zany fun film is worth the watch, so go see it!

10. Just One of the Girls

How about a gender-bending comedy that also crosses sexuality lines? This is the unintended results of what the main character did in Just One of the Girls.

Starring ‘90s teen heartthrob Corey Haim, the 1993 film is about his character named Chris, the victim of endless bullying by popular muscular jocks. So he tries to avoid getting roughed up on the way to school by dressing like a girl. When he gets to school, he dresses back as a boy.

But soon enough, he finds dressing like a girl as a hoot, because he can do many things that he can’t as a boy. And this is why it’s on our list of movies like She’s The Man. This time, he’s the woman trying to figure out how women really are. In the process, he also understands how some men are.

This kind of confusion gets muddled when attractions entangle people’s lives. A jock bully gets a crush on Chris while he’s dress as a girl. Meanwhile, Chris himself gets attracted to the jock’s sister, and falls for her. He gets mistaken for a lesbian, and someone also gets mistaken as a gay man here. And Chris is also suggested to admit being a transvestite!

Oh, the conflicts! Go see this one and laugh your heart out!

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