Zach Siler (Freddie Prinze, Jr.) is the hottie popular soccer player and Class President of his high school. On the day back from Spring Break, his popular prom queen shoe-in girlfriend Taylor Vaughn (Jodi Lynn O'Keefe), dumps him for the slimey big-headed TV reality star Brock Hudson (Matthew Lillard). In react, Zach alleges that Taylor is replaceable by anyone else, once placed in the right situation. That's when Zach's best friend, Dean Sampson (Paul Walker), says it's impossible. He challenge Zach to make a bet on whether or not Zach can turn any girl he chooses into prom queen within six weeks. While walking around the school, Dean picks out Laney Boggs (Rachael Leigh Cook) as his choice for Zach to turn into prom queen. Laney is a no-mother keen art geek who’s taking care of her little brother Simon (Kieran Culkin) her father Wayne (Kevin Pollack) after the death of her mother.

Zach embarks on the mission to turn Laney from a nobody into a prom queen. The first time Zach tries to approach Laney, she leaves him feeling weird. He goes to the fast food where she’s working, and ask her to help him with his passion for art. Thanks to the intrusion of her friend Jesse Jackson (Elden Henson) Laney accepts to go out with Zach for an art performance. Zach feels uneasy at the impressive show where she has a part, until the main artist calls him on stage for a little taste of his art. Nervously Zach start to play with a little ball, representing his uncomfortable feeling about always come up to people expectations. The day after Zach convinces Laney to go to the beach with him, but they’re joined by Zach’s friends. After a day spend playing beach volley, Dean invites Laney to join them to the night party in the house of  Zach’s friend Preston (Dulé Hill). She first accepts the invitation. But she change her mind, and tells Zach that she’s busy, that she must clean the house.

Zach arrive at her home with the kids of the young soccer team he’s training, and with his sister Mackenzie (Anna Paquin), to arrange the house and Laney respectively. Mackenzie helps Laney to take awareness of her womanliness and beauty, changing her hairstyle and turning her into a hot girl.Though once Laney scraps her glasses, does her hair, and gets into decent rags, Zach finds himself taking rather a lot of notice of her. At a party, Zach notice the presence of Taylor and her crazy boyfriend. When Taylor notice Laney, she confronts her, spilling her drink on Laney’s dress. Laney run off, followed by Zach. The next day, at school Laney founds that she was nominated for Prom Queen, the same news come into Taylor’s hears, while she’s upset because Brock dupms her just after the party.

After a soccer training, Dean accuses Zach of mixing business with pleasure and he doesn't mind if he gets a little action himself from Laney. Zach and Dean have a little push and shove. In the cafeteria, Zach defends Laney’s brother Simon, who’s working in there, form two jerky bullyboys, but his bet is preventing him from his true feelings with Laney, so he’s avoiding her. Dean comes to Laney’s workplace where he asks her to the Prom, but she refuse. Dean put some doubts in her mind about Zach’s real feelings, and the day of the Prom, when Laney is  talking with Dean, she’s confronted by Zach about going to the prom with Dean instead of him, and Dean reveals the bet to Laney. Laney is so upset that she refuses to go to her senior prom, but Dean shows up to pick her up. Taylor ask Zach to the Prom, but he decide to take his sister.

At the prom, Laney is approached by her art teacher and said that she was proud of Laney's final project. The teacher tells Laney also that whatever has brought that spark out in her to not let it go. Laney looks at Zach, dancing with Taylor, with emptiness. Meanwhile, Mackenzie meets Jesse, and they found to have a lot of things in common. In the bathroom, Jesse overhears Dean telling everyone that he’s reserved an hotel room and that he's going to get 'lucky' with Laney that night. Jesse and Mackenzie runs to tell Zach. The Prom King and Queen are announced. Zach is picked Prom King. The announcer says that it was a close race, but Taylor eventually wins Prom Queen. Zach finds out about Laney and Dean too late; they had already left.

Laney arrives at her house. Zach is revealed to be there as Laney explains how she fought Dean off using a device that is as loud as a foghorn, which she put next to his ear. Zach reveals his true feelings for Laney and asks for forgiveness.

The film was one of the main inspirations for the parody Not Another Teen Movie.

The school, Torrance High School, was also used for filming Not Another Teen Movie. The school has served as Sunnydale High in Joss Whedon's TV series, Buffy the Vampire Slayer and also appears as the high school in Beverly Hills 90210.

Freddie Prinze's foot double in the Hacky-Sack scene was professional footbagger "Big Add" Chad Devlahovich.

Rachael Leigh Cook's character's name, Laney Boggs, is a combination of the names of two characters played by Winona Ryder: Kim Boggs in Edward Scissorhands (1990) and Lelaina "Laney" Pierce in Reality Bites (1994). This is an apparent nod to Cook's and Ryder's physical resemblance.

In one scene, a copy of John Irving's book "The Cider House Rules" is visible in the background behind Kieran Culkin. Culkin played Buster in The Cider House Rules (1999).

Zach doesn't want to go to his Dad's alma mater, Dartmouth. His dad is played by Tim Matheson who starred in Animal House (1978), which was partly inspired by one of its writers time at Dartmouth. At the end of Animal House, Matheson is said to move to California and become a Doctor... which he is in She's All That.

Sarah Michelle Gellar make a cameo in the cafeteria.

Kevin Pollak is repeating the ongoing joke, which is about guessing wrong in jeopardy all the time. He originally did this in Truth or Consequences, N.M. (1997).

The Prom dancing sequence originally wasn't scripted and wasn't going to be filmed. It was added in at the last minute to make the movie go a few extra minutes.

The character "Brock Hudson" was actually named after a real life student of the same name at St. John's School in Houston, Texas. (The same school where Rushmore  was filmed). The screenwriter Lee Fleming went to this school, along with Wes Anderson (director of Rushmore and Bottle Rockets) and Will Wallace (The Thin Red Line and I am Sam) where the phrase "what kind of name is Brock Hudson?" was commonly heard.

M. Night Shyamalan reportedly did a script polish for this film.

The film contains several hidden references to the pop group Hanson, aisde from the photograph during Taylor's campaign. The two main characters are named Taylor and Zach - two of the members of Hanson. Mackenzie, and Jesse - two minor characters, were younger members of the Hanson family.

Zach Siler: Has anyone see Taylor?
Chandler: What?
Zach Siler: You know, Taylor, my girlfriend?
Dean Sampson: Kinda tall, yells at everyone?

Dean Sampson: I mean, the girl's an institution in this place. Every girl wants to be her, and every guy wants to nail her.
Preston: Basically she's you, with tits.

Dean Sampson: One second, you're Zach Siler, class president, stand-out athlete, all-around bad-ass mamba-jahamba; the next thing you know, you're Zach Siler, bitch-boy.

Dean Sampson: His dad owns Harrison Ford.
Laney Boggs: The actor?
Dean Sampson: No, the car dealership.

Dean Sampson: Is that a no?
Laney Boggs: That's a hell no.