In 1974 Pawtucket, Rhode Island, Tim Dunphy (SHAWN HATOSY) is a deadbeat seventeen- year-old who likes to hang out with his friends, including "Drugs" Delaney (JON ABRAHAMS) and Mousy (JONATHAN BRANDIS), getting high and thinking about sex. That's when he's not helping his wheelchair bound younger brother, Jackie (TOMMY BONE), deliver papers or trying to avoid his stern and rough around the edges father (ALEC BALDWIN) who not-so- affectionately calls him "Dildo."
When Tim rear-ends a parked police car while high on pot, old man Dunphy, who spends his time either playing poker with his buddies, including Joey (GEORGE WENDT), or eating ice cream from the carton while watching TV, sends Tim off to a prep school -- Cornwall Academy for Boys -- to prevent his son from serving any time for his crime.
Although he initially sticks out like a sore thumb, with the help of his new roommate Irving "Jizz" Waltham (JACK FERVER), blue-blooded student Jack Wheeler (GABRIEL MANN) and Billy Fu (ALEX TOMA), whose father's pending multimillion-dollar donation allows him to get away with anything, Tim soon begins to fit in. That's actually more so with the school's other troublemakers, much to the chagrin of Mr. Funderberk (TIMOTHY CROWE), the dorm resident director.
Things begin to look up for Tim when he spots and then falls for Jane Weston (AMY SMART), a pretty blond who's looking forward to attending Brown college. While she initially rebukes his advances, the two soon become an item. As the school year unfolds, Tim finds that he must balance that relationship while coping with his dad and the daily tribulations of attending a private and very strict boy's academy, all while learning a thing or two about growing up.