Perhaps the most genuine, slapstick, teenage comedy since “Fast Times at Ridgemont High” — which should hopefully liberate a generation from the notion of Alicia Silverstone and “Clueless.” Sitting atop the school’s pecking order is Zack (Freddie Prinze Jr.), the class president, soccer star and doer of no wrong. The world is veritable Eden for Zack, until his girlfriend, Taylor (a comely and snobbish Jodi Lynn O’Keefe) drops him for a former cast member of “The Real World” — played by Matthew Lillard with all the offensive pizzazz of the notorious, and soon-to-be-forgotten, Puck. Heartbroken and licking his wounds, Zack undertakes an ill advised bet to transform the school’s resident fem-dork, Laney (Rachel Leigh Cook wonderfully reminiscent of Winona Ryder’s brown-eyed Goth from “Bettlejuice”) into a suitable Taylor replacement and the next prom queen.
Predictably, but not without angst, Laney morphs from ugly-duckling into a blossoming beauty, and Zack’s materialistic heart sees the light of the human soul. The tempo of the film does well to cure the unlikely romance with just the right amount of anxiety and the leads — especially Cook, who is wonderfully promising here — create an earnestly heartfelt chemistry. The supporting cast, which features Kevin Pollack as Laney’s “Jeopardy” challenged father, Kieran Culkin as her peevish brother and Elden Hensen as her confidant are quite good and the pumping prom dance sequence (done to Fat Boy Slim’s “Rockafeller Skank”) is an outrageously slick piece of choreography.