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Five high school students from different walks of life endure a Saturday detention under a power-hungry principal. The disparate group includes rebel John, princess Claire, outcast Allison, brainy Brian and Andrew, the jock. Each has a chance to tell his or her story, making the others see them a little differently -- and when the day ends, they question whether school will ever be the same.
After high school slacker Ferris Bueller successfully fakes an illness in order to skip school for the day, he goes on a series of adventures throughout Chicago with his girlfriend Sloane and best friend Cameron, all the while trying to outwit his wily school principal and fed-up sister.
Two unpopular teenagers, Gary and Wyatt, fail at all attempts to be accepted by their peers. Their desperation to be liked leads them to "create" a woman via their computer. Their living and breathing creation is a gorgeous woman, Lisa, whose purpose is to boost their confidence level by putting them into situations which require Gary and Wyatt to act like men.
Buck Russell, a lovable but slovenly bachelor, suddenly becomes the temporary caretaker of his nephew and nieces after a family emergency. His freewheeling attitude soon causes tension with his older niece Tia, loyal girlfriend Chanice, and just about everyone else who crosses his path.
With the occasion all but overshadowed by her sister's upcoming wedding, angst-ridden Samantha faces her 16th birthday with typical adolescent dread. Samantha pines for studly older boy Jake, but worries that her chastity will be a turnoff for the popular senior. Meanwhile, she must constantly rebuff the affections of nerdy Ted, who is unfortunately the only boy in school who seems to take an interest in her.
Andie is an outcast, hanging out either with her older boss, who owns the record store where she works, or her quirky high school classmate Duckie, who has a crush on her. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realize that dating someone from a different social sphere is not easy.
Bill is a penniless drifter who scams strangers out of just enough money to feed himself and his partner in crime, an orphan girl known as Curly Sue. Bill and Curly Sue target Grey, a yuppie lawyer, but their con takes an unexpected turn when the successful woman begins to like the ramshackle duo. But there's one problem—Grey's jealous, conniving boyfriend, Walker.
It's vacation time for outdoorsy Chicago man Chet Ripley, along with his wife, Connie, and their two kids, Buck and Ben. But a serene weekend of fishing at a Wisconsin lakeside cabin gets crashed by Connie's obnoxious brother-in-law, Roman Craig, his wife, Kate, and the couple's two daughters. As the excursion wears on, the Ripleys find themselves at odds with the stuffy Craig family.
Jake and Kristy Briggs are newlyweds. Being young, they are perhaps a bit unprepared for the full reality of marriage and all that it (and their parents) expect from them. Do they want babies? Their parents certainly want them to. Is married life all that there is? Things certainly aren't helped by Jake's friend Davis, who always seems to turn up just in time to put a spanner in the works.
A group of teenagers wish to rebel against the administrators and teachers (the system) in their suburban Chicago high school called New Port South