This is a story we've seen a lot in comedy — a woman or man swapping clothes for laughs — but here, director Andy Fickman wants to make a bigger point. Sure, it's funny to watch Viola try to become a guy, but there's nothing funny about why she's becoming one. She's standing her ground and making a choice to be the kind of woman who takes action when others try to keep her down. Viola's powerful transformation proves that masculine and feminine are all in the eyes of the beholder. But ultimately, this is still a man's world. In order for a woman to be taken seriously, she has to be dressed as a man.

Bynes' character struggles to be feminine enough for her mom, who wants to see her as a debutante in frilly dresses — even though Viola has a "strict no-ruffles policy" and believes heels were invented by a man to make women's butts look smaller. Oh, and also to make it harder for them to run away. She rails against the idea that the pageantry her mom so wants her to be a part of makes her more of a woman than being powerful and strong on the soccer field would. Her ex-boyfriend says things like, "Be a girl for five seconds," when she begins to talk about soccer instead of their relationship.

But while posing as Sebastian, Viola hardly struggles to fit in with her male classmates, who include her roommate and teammate (and eventual crush), Duke Orsino, played by a pre-Step Up Channing Tatum. With just a wig, a little extra facial hair and an ACE bandage to tape down her breasts, she looks just like one of the guys. But can she act like one? Viola initially tries too hard to be what she thinks a man should be. She tosses off a little too much bro language, throwing in a "brah," "dawg," or "G-money" (remember, this was 2006). But her sensitive side gives them pause. When one of her teammates asks. “Is your sister hot?” her response — “I guess so, she’s got a great personality" — gets a very disappointed, “Ew."

But these guys come around once they realize "Sebastian's" ability to understand the opposite sex is a skill they don't have, but want. Here, being a woman actually gives her a leg up with these men. It also shows that she's perceived as male just by looking like one, not by acting a certain way. "Sebastian's" honesty is what the pretty blonde Olivia (Laura Ramsey) notes as being the reason she's attracted to him. Olivia likes the fact that he admits he doesn't have the stomach to dissect a frog. These traits that are often described as feminine make Sebastian a real man in Olivia's eyes.