She's All That - 1999

Zach Siler (Freddie Prinze, Jr.)—soccer star, class president, honor student—is the big man on campus at his California high school. At the outset of the film, his popular girlfriend, Taylor Vaughn (Jodi Lyn O'Keefe) dumps him for a faded reality TV star from The Real World, Brock Hudson (Matthew Lillard), whom she met on spring break. Although he is hurt by Taylor's rejection, Zach consoles himself by saying that Taylor is replaceable. Zach's friend, Dean Sampson, Jr. (Paul Walker), disagrees. They make a bet on whether or not Zach can turn any girl into the Prom Queen within six weeks. While walking around the school, Dean picks out Laney Boggs (Rachael Leigh Cook), a morose, but highly responsible, art student, as his choice for Zach.

Zach approaches Laney in the attempt to transform her into the prom queen. His first encounter with her is a failure, when she pointedly ignores his attempt to befriend her. Laney's little brother, Simon (Kieran Culkin), continuously talks Zach up to Laney. Zach is eventually successful in getting Laney to invite him to a lounge that is frequented by artists and performers with help from Laney's friend Jessie (Elden Henson) against Laney's wishes. Laney performs a contemporary and interpretive performance. Afterwards, Zach is invited to take the stage. At this point, Zach improvises and performs with the hacky sac in his pocket. Laney is amused by Zach's performance but rejects him after he makes a move on her. He continues to attempt to see her by becoming friends with her brother and, in an attempt to stop this, Laney agrees to see him and they go to the beach together. He successfully persuades her to come to a party at Preston's house the same night, by employing his sister Mackenzie Siler (Anna Paquin) to give her a makeover and making the JV soccer team clean her house. At the party, showing off her new look, Laney is humiliated by Taylor, but is consoled by Zach.

During these outings, Zach's friend Dean begins to show an interest in Laney as Zach's victory becomes more and more imminent - primarily a sexual interest. Dean also invites Laney to the prom, in an attempt to ruin Zach's attempt at winning the bet. As a result of her new look and Zach's interest, Laney is nominated for Prom Queen and this begins a battle between Laney and Taylor Vaughn for the crown. Dean, angry after a fight with Zach, tells Laney about the bet and she forces him to reveal the truth about the bet in public, to her (and his) great embarrassment. Zach ends up attending the prom with his sister, while Taylor arrives alone, thinking that Zach is still interested in her. On prom night, Dean shows up at Laney's house in a tuxedo; Laney reluctantly changes clothes and goes to the dance with him despite turning him down previously.

At the Prom, after an in-depth dance-scene, presided over by the schools resident DJ (Usher Raymond) Zach's sister Mackenzie meets Jessie and they become friends. Drunk, Dean boasts in the bathroom that he is going to a hotel room with Laney, Jessie overhears this and warns Zach. Taylor is then crowned Prom Queen with just over half the votes; She begins a long moaning speech which is interrupted by her microphone being turned off by a teacher. Laney and Dean leave together.

When Laney arrives at her house, Zach is waiting for her. Laney explains how she fought off Dean's advances, deafening him with her rape alarm, and left him at the hotel. Zach reveals his true feelings for Laney and tells her that she has taught him valuable lessons. He asks for forgiveness and the chance to have something more than just a friendship, which she grants. Laney tells Zach that she is considering art school; Zach then tells her that she has inspired him to pursue a career in performance art. They also joke about the 1990 film Pretty Woman.

At the graduation ceremony, Zach must make good on his bet with Dean by appearing nude on stage. After his name is called, Zach heads to the stage, carrying a soccer ball to cover himself, but then tosses the ball to Laney.