Set in the stereotypical high school community of John Hughes High, the movie unravels when Priscilla (Jaime Pressly), a popular cheerleader, separates from her boyfriend, Jake Wyler (Chris Evans). After Jake discovers that Priscilla is now dating strange and socially inept Les (Riley Smith) just to spite him, one of Jake’s friends, Austin (Eric Christian Olsen), suggests seeking retribution by making Janey Briggs (Chyler Leigh), a "uniquely rebellious girl", the prom queen. Jake attempts to court Janey's love, but faces adversity from his own sister Catherine (Mia Kirshner), who is sexually attracted to him, Janey’s unnoticed admirer and best friend Ricky (Eric Jungmann), and memories from his past football career. Catherine eventually helps her brother by slightly altering Janey’s appearance, ultimately making her more attractive to the other characters.
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, as he'd caused Marty's death a year before, when passing to him (against his coach's wishes), scoring a touchdown... and subsequently being ripped in two by the opposing team when they tackled him. The situation is further worsened when Austin tricks Jake into telling Janey about his plan to spite Priscilla by pretending to whisper the secret bet in Janey's ear, causing her to immediately leave Jake. During prom night, Janey eventually attempts to leave her troubles behind by leaving the country, and pursuing her life-long goal of being an artist in an art school in Paris. However, Jake confronts her before she can board the plane, and uses a plethora of clichéd lines from other movies (such as She's All That, Cruel Intentions, American Pie, The Breakfast Club, and Pretty in Pink) to convince her to stay in America. His final (and first original) speech suggests they would be better off apart, but Janey mistakenly believes he's quoting The Karate Kid, and she decides to stay with him, which is a nod to the ending of many teen movies.
Mia Kirshner as Catherine Wyler (The Cruelest Girl in School) - She is sexually attracted to her younger brother Jake, is very promiscuous, and helps other get popular. She teaches Sadie the basics in a reference to the 1999comedy, Never Been Kissed. Primarily based on Kathryn Merteuil (played by Sarah Michelle Gellar), in Cruel Intentions. Furthermore, she is partially based on the character of Mackenzie Siler (played by Anna Paquin) from She's All That.
Deon Richmond as Malik Token (The Token Black Guy) - He's just supposed to smile, stay out of the conversation, and say things like, "Damn!", "Shit!", and "That is whack!" A reference to Dule Hill's character Preston in She's All That.
Eric Jungmann as Ricky Lipman (The Obsessed Best Friend) - He is Janey's best friend who is also madly (and explicitly) in love with her, though Janey remains completely clueless (the only person in the school apparently not aware of his love for her). He also composes a list of the 10 Things I Love About Janey Briggs in a reference to 10 Things I Hate About You. A parody of Jon Cryer's Duckie in Pretty in Pink.
Ron Lester as Reggie Ray (The Stupid Fat Guy) - He has several concussions throughout the film (hit by a locker, crashing into a wall, hit in head with football). He is a parody of Lester's character from Varsity Blues.
Cerina Vincent as Areola (The Naked Foreign Exchange Student) - Although the school claims a strict dress code, she is naked throughout the entire film. Her accent also changes frequently throughout the movie, Janey notices this and Areola tells her she is a generic foreign exchange student whose country of origin is of little importance. An adaptation of the foreign exchange student Nadia (Shannon Elizabeth) in American Pie. Her name is also the word for the ring around the nipple.
Riley Smith as Les (The Beautiful Weirdo) - He is always seen with a video camera and a floating bag following him around known as "The Most Beautiful Thing I've Ever Seen", referencing the bag floating in the wind from American Beauty. A parody of Wes Bentley's character in American Beauty. His name may also be a reference to the main character of that film, Lester.
Beverly Polcyn as Sadie Agatha Johnson - A well-past-60-year-old undercover reporter who is taught how to make love by Catherine. She is a parody of the Drew Barrymore character in Never Been Kissed.
Many stars of recent teen movies as well as those highlighting the 1980s decade make credited and uncredited appearances. These include:
Molly Ringwald as The Rude Flight Attendant - A rude flight attendant at the airport near the end of the film who insults Jake and Janey. Ringwald starred in many '80s teen movies.
Kyle Cease as The Slow Clap Guy - A guy present throughout the film looking for the right moment to start the slow clap, he beats up Ricky for beating him to the slow clap at the end of the film. Cease played Bogey Lowenstein in 10 Things I Hate About You.
Paul Goebel as The Chef Who Ejaculated Into Mitch's French Toast - A brief cameo during the Prom Tonight musical number who told Mitch he ejaculated into his French toast. Parodies Horatio Sanz's character from Road Trip || Goebel is known as the TV Geek from Beat the Geeks.
Good Charlotte as The Band - The band playing at the prom.
China Shavers as The Rival Cheerleader - A black girl who Priscilla tells to "bring it!" A parody of "Bring it on." Shavers was in the teen drama Boston Public, and appeared as Dreama on Sabrina, the Teenage Witch.
Josh Radnor as The Tour Guide - Asks why hot girls always walk so slow. A parody of Tom Green's character, Barry Manilow in Road Trip.
Ean Mering as Marty, The Nerdy Boy Playing Football in the Daydream - Jake says, "I say we give the ball to Marty". Spoof of Lucas, a nerdy, intelligent glasses wearing geek who joins the football team in an attempt to impress a cheerleader, Maggie. Marty says, "That's okay guys, I'm just happy being on the field." Later an accident in the football game leaves him severely injured. Parody of Lucas and Rudy.
Extra footage
Alternate footage
Three scenes that appear on the R-rated trailer are not included in the film: a scene that spoofs Save the Last Dance where a girl is dancing at the big party, a scene that spoofs Never Been Kissed during the football game with Sadie standing on the football field with a microphone, probably speaking to Catherine, before the entire football team runs her down, and a small scene with Areola asking the principal if her breasts are perky (this scene does appear in the unrated cut of the film).
In the trailer for the film, Jake wears boxer shorts during the whipped cream bikini scene, whereas during that same scene in the film, his bare crotch is covered with whipped cream instead of the shorts.
Footage during credits
The film has three extra scenes at the end:
Mitch, Ox, and Bruce talking about what they learned from the whole experience. (This scene comes only in the unrated cut.)
Mr Briggs, in a parody of a scene from "American Pie", talks about a "three-way" while holding two pies. (This scene comes only in the rated cut.)
The albino folk singer sings about being blind, and her corneas being burned out by the sun. (This scene comes after all the credits have finished.)
DVD release
The R-rated version of the film was released on DVD on April 30, 2002 with the original 89-minute cut with special features including:
School's in Session: 3 behind-the-scenes featurettes
The Unrated Extended Director's Cut was released July 26, 2005 with all of the original special features including an added 10 minutes to the film adding up to 100 minutes.
Soundtrack listing
The soundtrack for the film features rock artists from the 1990s and 2000s, mostly covering songs from the 1980s, and this CD was released by Maverick Records in 2001.
Prom Tonight (Ben Folds, Mike Bender, Adam Jay Epstein and Andrew Jacobson) - Jake, Janey, Mitch, Ox, Bruce, Catherine, Priscilla, Mr. Briggs, Austin, Malik, Areola