It features Chyler Leigh, Chris Evans, Jaime Pressly, Eric Christian Olsen, Eric Jungmann, Mia Kirshner, Deon Richmond, Cody McMains, Sam Huntington, Samm Levine, Cerina Vincent, Ron Lester, Randy Quaid, Lacey Chabert, Riley Smith and Samaire Armstrong.

The general plot is primarily derived from She's All That,[3] as well as 10 Things I Hate About You,[3] Can't Hardly Wait,[3] Pretty in Pink, and Varsity Blues.

[4] It is also filled with allusions to other films featuring teen and college-aged characters, such as American Beauty,[4] American Pie, Bring It On, Can't Buy Me Love, Cruel Intentions,[5] Dazed and Confused, Fast Times at Ridgemont High, Ferris Bueller's Day Off, Grease, Jawbreaker, Lucas, Never Been Kissed, Risky Business, Road Trip, Rudy, and Sixteen Candles, while Paul Gleason reprises his role as Vice Principal Vernon from The Breakfast Club.

Discovering she is now dating timid and weird Les to spite him, one of Jake's friends, Austin, makes a bet with him to turn nerdy Janey Briggs into the prom queen.

Catherine assists him by "drastically" altering Janey's appearance (removing her glasses and ponytail), instantly making her drop-dead gorgeous.

The musical number, "Prom Tonight", written by Ben Folds, Michael G. Bender, Adam Jay Epstein and Andrew Jacobson, is a parody of Grease.

[7] A karaoke version of the ending to "Can't Fight this Feeling" by REO Speedwagon is used each time Amanda Becker enters a scene.

Songs not included on the soundtrack include "Line Up" by Elastica, "In Between Days" and "Turning Japanese" by Face to Face, "Lucy", "Don't You Forget About Me", "Everybody Knows Everything" and "Friends" by Sprung Monkey, "Yoo Hoo" by Imperial Teen, "Double Dare Ya" by Bikini Kill, "Rock Star" by Everclear, "Oh Yeah" by Yello, "Kiss Me" by Sixpence None the Richer, "Let's Go" by the Cars, "Pacific Coast Party" by Smash Mouth, "Let's Begin (Shoot the Shit)" by Bad Ronald, "True" and "King of Yesterday" by Jude, "900 Number" by The 45 King, "My Hero" by Foo Fighters, "I Want Candy", "Put Your Head on My Shoulder" and "Footloose" by Good Charlotte, "Space Age Love Song" by No Motiv, and "If You Were Here" by Thompson Twins.

[11] Roger Ebert of the Chicago Sun-Times gave the film two stars out of a possible four, and admitted to laughing a few times but not as much as he did for American Pie or Scary Movie.

[12] Robin Rauzi of the Los Angeles Times called it "a 90-minute exercise in redefining the word 'gratuitous'" and suggested it is most likely to appeal to fourteen-year-olds – "who of course [are] not supposed to be seeing this R-rated movie".

[5] Dennis Harvey of Variety criticized the film for its "overall tendency to mistake mere bad taste for outrageousness, and plain referentiality for satire" but praised Evans, Pressly, and Olsen for giving performances better than the material.