Set in the fictional John Hughes High School, Not Another Teen Movie is a parody of popular teen films from the 1980s and 1990s. The story follows Jake Wyler (Chris Evans), a stereotypical high school jock, who accepts a bet to transform Janey Briggs (Chyler Leigh), an βunattractiveβ and artistic girl, into the prom queen. Janey, of course, fits every clichΓ© of an overlooked girl: glasses, a ponytail, and paint-stained overalls.
Jake’s bet is initiated by his ex-girlfriend, Priscilla (Jaime Pressly), the quintessential mean cheerleader. Jake teams up with his friend Austin (Eric Christian Olsen) to win the bet while navigating the antics of their classmates. These include Malik (Deon Richmond), the token Black friend who constantly reminds everyone of his stereotype, and Ricky Lipman (Eric Jungmann), Janeyβs overly obsessed childhood friend. The film also introduces Catherine (Mia Kirshner), Jakeβs seductive stepsister, who provides inappropriate advice.
As Jake spends more time with Janey, he begins to genuinely like her, complicating his bet. Meanwhile, the film delivers a constant stream of parody, mocking iconic moments from teen movies such as Sheβs All That, 10 Things I Hate About You, American Pie, and Never Been Kissed. Highlights include a hilariously exaggerated football scene, a musical cafeteria number reminiscent of Grease, and Janeyβs infamous slow-motion prom entrance after her makeover.
At the prom, Jake confesses his feelings for Janey but is exposed for his original bet, causing her to reject him. However, after a series of comedic and over-the-top events, Jake redeems himself by recreating a grand romantic gesture, parodying Say Anything and Canβt Hardly Wait. Janey forgives him, and they share a kiss, while the other characters resolve their storylines in similarly absurd and exaggerated ways.