Gumdrop Lane

The Best and Worst of Girls Dressed As Guys in Film

For most of us living as females, we’ll never have to disguise ourselves as a man to get where we need to go in life. Sure, some of us might need to don a pantsuit, a skirtsuit, even a skortsuit or engage in other traditionally masculine pursuits (because if there’s one thing men love it’s wearing a skortsuit)  – but generally none of us will have to pose as a dude to achieve our dreams.

However, in film this is not the case. In film, the most obvious solution to many lady problems is to pretend you’re a guy. You’ll have to wear a wig, glue hair to your face, lower your voice and/or stuff a sock down your trousers. It’ll just make sense. Some actresses pull this off better than others.

What qualifies as “best” in this list is not necessarily what is most authentic – it’s a lady’s devotion to one’s character in stressful situations. What defines the “worst” is completely up to me – and I happen to dislike terrible facial hair and ill-fitting clothing.

Here are the best and the worst of girls disguised as guys in film:

The Best…


Julie Andrews is completely devoted to her man character in this film. She’s a lady posing as a man posing as a lady. She fools audiences the world over. She looks great with a cigar. She sings like a lady bird posing as a man bird posing as a lady bird. She wears a tuxedo! Only men can wear tuxedoes. She’s brilliant.

The Associate

It’s Whoopi! Whoopi is courageous in the role of Laurel Ayres, a black woman who is forced to transform herself into Robert Cutty, a white man, in order to make it on Wall Street. If turning your adorable crazy Whoopi self into a fat ugly mansack with stringy white hair isn’t one of the toughest hurdles to hoist yourself over, then I guess I just don’t know tough hurdles.


Mulan volunteers herself to go into battle instead of her father and has to pose as a boy in order to do it. Mulan is not only brave and selfless, she also has to cut her long luxurious hair. A true American hero…who is actually a Chinese girl…who is actually just a Disney character…

She’s the Man

This movie is absurd. Amanda as a boy is absurd. The whole film is absurd. But it’s also amazing. Amanda commits herself to her manhood in the name of soccer. There is no nobler cause. My friend and I actually forfeit a day of sightseeing in a Denmark to watch She’s the Man for the umpteenth time. Ump. Teenth.  I regret nothing.

30 Rock

Jenna transforms into a black man, while Tracy transformed into a white woman. Jenna probably just watched The Associate and wanted to turn the world’s idea of who can transform from black to white or white to black on it’s head. And turn it she did. And I gotta say, I didn’t hate it.

Twin Peaks

Catherine Martell truly takes the cake as one of the all-time great gender-bending/race-bending transformers. It does not get much more bold or daring than this: going from a horrible and sassy white lady to portraying a mysterious Japanese business man with terrifying realism.

and The Worst…


So this movie was just horrible. Did I laugh? Oh, yes. But it was a laughter I did not enjoy. It was the cold, joyless laughter of having paid to see this in the theatre. The kind of laughter that makes you want to take a scalding hot shower, just so you can feel alive again.

There were so many terrible things about this film that Angelina dressing up as a male Secret Service agent really just put the moldy butt on top of a crap sundae. I’m pretty sure it was totally unnecessary. The whole movie was unnecessary. I’d love to wipe her terrible turn as a man from my memory, but I don’t think I have enough toilet paper to clean up the mess.

Shakespeare in Love

This happens to be a wonderful movie. I love it. I’ll watch it a million times. But Gwyneth’s turn as a man? Not too impressive. She barely lowers her voice to a comical degree and her sad little beard is not hiding the fact that she has no other discernible stubble and just the tiniest little eyebrows. Plus, she basically drops her pantaloons the moment Shakespeare’s call, “Drop those pantaloons.”

Ladies, never drop your pantaloons just because Shakespeare orders it. What’d he ever do? Did he ever take you to Red Lobster and tell you to get whatever you wanted? Anything on the menu? And a drink? Whatever drink you wanted? Because if he did, that’s a different story entirely and I retract my earlier remarks about not dropping your pantaloons.

Charlie’s Angels

They’ve got the stubble and big ole fluffy eyebrows, so what’s the problem? Ill-fitting ugly suits. Can’t stand for it, won’t stand for it and I don’t.

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