Legally Blonde (PG-13)
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This came out in 2001, and I reckon I must have first seen it sometime in the early-to-mid Aughts. But that was before I started writing reviews, so I didn't get around to reviewing it until I watched it again in 2016.
Elle Woods (Reese Witherspoon) seems like a stereotypical shallow, dumb blonde. At the start of the movie, she believes her boyfriend, Warner Huntington III, is going to propose to her. Instead, he breaks up with her, believing he will need to marry a more "serious" woman, in order to eventually pursue his planned political career. Elle is devastated at first, but soon decides to make herself into a "serious" woman, by applying to Harvard Law School. It's kind of comically easy for her to gain admission ("what, like it's hard?"), but once she gets there, things do get hard. One of her classes is taught by a Professor Stromwell (Holland Taylor), who doesn't seem to think much of her. And she soon discovers that Warner is now engaged to another law student, Vivian Kensington (Selma Blair), who definitely doesn't think much of Elle. However, Elle befriends a young lawyer named Emmett (Luke Wilson), who works with another of her professors, Callahan (Victor Garber). She also befriends a manicurist named Paulette (Jennifer Coolidge).
Once Elle finally realizes that Warner doesn't respect her, she wants to quit school, but... for a reason I won't spoil, she decides to stick it out. Anyway, Prof. Callahan apparently thinks she's got potential, and includes her on his team of students that will be working with him on a real trial. The team also includes Warner and Vivian, as well as Emmett (and others of less importance). They're defending a woman named Brooke Taylor-Windham (Ali Larter), who is accused of murdering her older husband. Elle is a fan of Brooke's, and the only one who really believes she's innocent. And I don't want to go into any more detail, but suffice to say Elle turns out to be a better lawyer than anyone (except Emmett and Paulette) ever expected.
So... it's a pretty funny movie, but also it rather shatters stereotypes. I mean, I think it would be perfectly reasonable at the start of the movie to totally believe Elle fits her "dumb blonde" stereotype (though there is an early indication that it's not reasonable). But I also think there's a certain amount of cultural programming that goes into it... not quite "internalized misogyny," per se, but... an internalized idea of how Elle and her sorority friends think they should be, how they should act, what they should care about... and the idea that those things are somehow incompatible with intelligence or depth. I don't think Elle ever saw herself as dumb or shallow, but I do think she sort of had a limited idea of... not so much what she could do, but of what she might want to do. And the neat thing about the movie is that she found she could change her ambitions without changing who she was; indeed, the things she knew because of the kind of person she was turned out to be unexpectedly, yet sort of believably, useful to her legal endeavors. All of which I think is a better message than if it turned out that because she's actually really smart, she must therefore completely change her personality and interests. (The school's admission board's idea that she represents "diversity" is still kind of ridiculous, considering she's a wealthy, conventionally attractive, white woman. But at least I'd say the movie is a good start towards spreading the idea that there isn't some one "right way" to be good at anything, to be worthy, or whatever.) And... I guess that's all I have to say. Except that Elle isn't the only character to bust a stereotype, or at least a movie cliche. (But most of the characters are pretty predictable, so I won't spoil which one I'm talking about.)
There's a sequel, Legally Blonde 2: Red, White & Blonde. And there's another sequel (or spin-off), which I think was direct-to-video (or maybe even a TV movie), which I don't intend to ever watch.