She's All That (1999)

★★★
My favorite shot in She’s All That lasts about five seconds at the end. Laney Boggs smiles as Zack Siler embraces being on the losing end of a bet. The camera zooms in on Laney, who's laughing with such gusto, like she just set free a lifetime of frustration. Sixpence None the Richer’s “Kiss Me” plays on the soundtrack. Credits roll. I love it. It summarizes her journey from unpopular art student to someone ready to combine her strengths with her newfound confidence and enter a new chapter in her life. It’s fitting that this movie came out in 1999. With the new millennium just around the corner, she has the opportunity to leave her old self behind and step into another era and start anew.

Maybe I’m reading too much into it. She’s All That has a lone screenwriter credited, one R. Lee Fleming Jr., but since M. Night Shyamalan had a role in strengthening the script, there’s no reason to think that something deeper isn’t going on in the story, which is otherwise a humorous modern-day retelling of George Bernard Shaw’s Pygmalion. It could all just be coincidence. If the movie had been released at any other time, I wouldn’t waste so much space discussing the implications of its narrative arc in relation to the year 2000. It’s fun to speculate about such things, though. A triple-zero year was coming; it was on everybody’s mind back then. Why wouldn’t someone insert a nod to this significant event, whether consciously or not?

Laney Boggs (Rachael Leigh Cook) is a social outcast, some of it self-imposed, some of it the result of a deceased mother. When we first meet her, she is hidden under eyeglasses, bad hair and baggy clothes. Her father is a pool cleaner, played by Kevin Pollak as a laid-back working-class guy. She has a brother, Simon, played by Kieran Culkin. Laney becomes the subject of a bet between Zack (Freddie Prinze Jr.) and Dean (Paul Walker). Zack says he can turn any girl in school into the prom queen, a bet that stems from his recent break-up from Taylor (Jodi Lyn O'Keefe), a stuck-up snobby elitist who is not only the front-runner for the title of Prom Queen, but who’s also now dating a reality T.V. star (Matthew Lillard). Zack, feeling exasperated that Dean picked Laney, nevertheless goes to work, inviting himself into Laney’s life. At first, Laney rejects Zack's advances, but the two gradually become friends and hang out together. Her father wants the best for her and encourages her to be a little more receptive of other people.

Their pairing eventually develops into something more meaningful. As Zack discovers more about Laney, he realizes that she isn’t just a dorky artist with paint on her clothes. She’s actually more complex than that, and very likeable once she comes out of her shell. Once Dean suspects that he might lose the bet, he decides to sabotage Zack’s momentum by injecting himself into the equation, warming up to Laney to make her go out with him instead. Dean reveals the big secret, and this leads to my biggest gripe about the movie, as Laney expresses her anger by demanding to know if she’s a “fucking bet.” I’m pretty sure this movie, which is largely absent of swearing, would have been rated PG-13 anyway due to some teen drinking and smoking, so her use of that word is unnecessary.

These characters represent various high school social groups, but juggles some of their traits to make them less predictable. Laney Boggs is pretty but insecure. Zack Siler is cocky but “has the fourth-highest G.P.A. in the class.” (Laney at first thinks Zack wants to be friends just to see if she’ll tutor him, even though she’s not smart.) Dean is who he is by necessity, as is Taylor, but other characters in their orbit, like Katie (Gabriele Union) and Preston (Dulé Hill), are sympathetic to Laney, while Laney’s art class friend Misty (Clea DuVall) gets drunk and insults her. Two years later, Not Another Teen Movie would mine this material for comedic affect. It’s ultimately silly, but the ambition was there. It knows the conventions of its formulaic plot, but doesn't fall victim to them.

Zack will lose the bet, as I’ve already stated. Whether we know that or not is irrelevant. What makes this movie worthy of a screening are the moments of light humor (like the graffiti on Mr. Pool’s truck) and the suspicion that She’s All That was aiming for a greater point to be made about experiencing hardship but finding the opportunity to move beyond it. My own high school years were far from perfect. I moved 6,000 miles away after graduation. New surroundings, new opportunities, with none of the baggage of the previous years to hover over me. That’s why I love the ending. It’s a simple gesture that carries a lot of significance. Whatever the future holds for Laney and Zack, one thing is for sure—they can press the reset button and begin again, only this time with a full appreciation of each other.

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