In the stereotypical high school community of John Hughes High in Southern California, attractive Priscilla (Jaime Pressly) (mainly based on Taylor Vaughan (Jodi Lyn O'Keefe) from She's All That, Big Red (Lindsay Sloane) and Torrance (Kirsten Dunst) from Bring It On, and Angela Hayes (Mena Suvari) from American Beauty), a popular cheerleader, separates from her talented football star but slacker boyfriend, Jake Wyler (Chris Evans) (("The Popular Jock"), mainly based on the characters Zack Siler (played by Freddie Prinze Jr.) from She's All That and Jonathan Moxon (played by James Van Der Beek) from Varsity Blues). After Jake discovers that Priscilla is now dating timid and weird Les (Riley Smith) (("The Beautiful Weirdo"), mainly based on Ricky Fitts (Wes Bentley) from American Beauty) just to spite him. Jake claims that given the right looks anyone can be prom queen, one of Jake's friends, Austin (Eric Christian Olsen) (("The Cocky Blond Guy"), mainly based on Dean Sampson, Jr. (Paul Walker) from She's All That and Steff McKee (James Spader) from Pretty in Pink), makes a bet with him to turn Janey Briggs (Chyler Leigh) (("The Pretty Ugly Girl"), mainly based on the characters Laney Boggs (played by Rachael Leigh Cook) from She's All That, Katerina Stratford (played by Julia Stiles) from 10 Things I Hate About You, and Andie Walsh (played by Molly Ringwald) from Pretty in Pink), a "uniquely rebellious girl," into the prom queen. Priscilla takes in Sandy Sue (JoAnna Garcia) (("The New Girl in School"), mainly based on Sandy (Olivia Newton-John) from Grease) as the new cheer girl in her group. Sandy has Tourette's syndrome. Jake is traumatized by events on the football field last season, when he went against his coach, to give the ball to a rookie during an end game play, and the rookie got clobbered by 2 defenders, splitting his body right down in half. Janey talks to her dad if she should go out with Jake, given that he has ignored her for 6 yrs. Her dad says yes, only if Jake is in it for the sex. Jake goes by Catherine's advice to win over Janey, but things go wrong (he punches Janey's brother Mitch when Mitch punches Jake after he saves Mitch from bullies. Jake sings a song "Janey's got a gun", which gets her arrested. He invites Janey home for a snack, and then proceeds to come out naked covered in whipped cream, and Janey leaves in disgust) Jake attempts to court Janey's love, but faces adversity from his own sister, Catherine (Mia Kirshner) (("The Cruelest Girl") mainly based on Kathryn Merteuil (Sarah Michelle Gellar) from Cruel Intentions and Mackenzie Siler (Anna Paquin) from She's All That), who is sexually attracted to him; Janey's unnoticed admirer and best friend, Ricky Lipman (Eric Jungmann) (("The Obsessed Best Friend"), mainly based on Duckie Dale (Jon Cryer) from Pretty in Pink); and memories from his past football career. Catherine eventually assists her brother by "drastically" altering Janey's appearance (which is simply removing her glasses and ponytail), instantly making her drop-dead gorgeous. Meanwhile, Janey's younger brother, Mitch (Cody McMains) (("The Desperate Virgin"), mainly based on Kevin Myers (Thomas Ian Nicholas) from American Pie and Simon Boggs (Kieran Culkin) from She's All That, as well as John Bender (Judd Nelson) from The Breakfast Club), and his friends Ox (Sam Huntington) (("The Sensitive Guy"), mainly based on Oz (Chris Klein) from American Pie) and Bruce (Samm Levine) (("The Wannabe"), mainly based on Daniel LaRusso (Ralph Macchio) from The Karate Kid, Jim Levenstein (Jason Biggs) from American Pie and Kenny Fisher (Seth Green) from Can't Hardly Wait), make a pact to lose their virginity by graduation despite still being in their freshman year. Mitch tries to impress his longtime crush, the beautiful yet perverted Amanda Becker (Lacey Chabert) with a love letter. Bruce says that he does not have a chance with her, mockingly stating, "Keep dreaming!" Jake takes Janey to a party after her "transformation". There Catherine hooks up with a 60+ years old woman who is a new student at the high school. Meanwhile Priscilla drops a bottle of water on Janey and calls her a loser. She cries and goes home. Jake goes after her and tries to console and kiss her in her basement. Later, the next day, Jake asks Janey out for prom, and she is also nominated for Prom Queen. As the prom draws near, Jake draws infamy among his peers after he fails to lead his football team to victory at the state championship game the year before (he blows the last pass). The situation is further worsened when Austin tricks Jake into telling Janey about his bet to spite Priscilla by pretending to whisper the secret bet in Janey's ear, causing her to immediately leave Jake in anger. During prom night, Austin and Janey go together; a jealous Jake and Catherine have a dance-off with Austin and Janey, with Catherine dancing in a sexual manner. Janey runs off crying. Meanwhile, Mitch and his friends are having a lousy time at the prom until Amanda (Lacey Chabert) (("The Perfect Girl"), mainly based on Amanda Beckett (Jennifer Love Hewitt) from Can't Hardly Wait) arrives and Mitch gives her the letter (to which she responds that she does not have sex with every loser who does such, but will give them hand jobs), horny Bruce hooks up with the equally horny international student Areola (Cerina Vincent) (("The Foreign Exchange Student"), mainly based on Nadia (Shannon Elizabeth) from American Pie), and Ox later hooks up with Catherine after sharing a romantic and rather odd connection. Jake is awarded prom king and the principal (George Wyner) reads out that the votes for prom queen are tied. Everyone thinks that it is between Janey and Priscilla, but they are shocked to find that Kara (Samaire Armstrong) and Sara Fratelli (Nectar Rose), conjoined twins, win prom queen. During the traditional prom king and queen dance, Janey supposedly left with Austin to go to a hotel. Jake goes to the hotel room where he finds Austin having wild sex with a girl but is shocked to find that it is Priscilla and not Janey, while Les videotapes them with his pants down. Austin tells Jake that Janey "ran home to her daddy." Jake coldly punches Austin and Priscilla, knocking them unconscious for their part in Janey's humiliation. He then punches Les for "being really weird" (he also punches a plastic bag that happens to be floating next to Les); afterwards he runs to Janey's house only to learn from her father that she is going to Paris for art school. Jake arrives at the airport and confronts her before she can board the plane but uses a plethora of cliched lines from other films (such as She's All That, Cruel Intentions, American Pie, The Breakfast Club, American Beauty, 10 Things I Hate About You, Can't Hardly Wait, and Pretty in Pink) to convince her to stay home in America. His final (and only original) speech suggests they would be better off separated, but Janey mistakenly believes he is quoting The Karate Kid, and she decides to stay with him. In a mid-credits scene, Janey's father Mr. Briggs (Randy Quaid) drunkenly assaults himself with pies in his kitchen. In a post-credits scene, an earlier seen Albino Folk Singer (Joy Gohring), a student with an Afro and with a guitar, reveals that she has become blind and calls out for assistance upon completing her song, while an audience member calls for another to assist in stealing her guitar.
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