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. Starting with Amanda Bynes in She's the Man
Julie Andrews in Victor/Victoria
Whoopi Goldberg in The Associate
Catherine Martell in Twin Peaks
Now the worst: Angelina Jolie in Salt
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.
Gwyneth Paltrow in Shakespeare in Love
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.
Cameron Diaz and Drew Barrymore in Charlie's Angels