Plot
Timothy "Dildo/Dunph" Dunphy (Shawn Hatosy), is a high school senior living in Pawtucket, Rhode Island, in 1974. He hangs out with a group of friends, mainly to smoke marijuana at the water tower overlooking town. His friend, Drugs Delaney (Jon Abrahams), suggests going out to a local bar called "The Edge,", which a sexually promiscuous classmate known as Bunny Cote is known to frequent.
Accepting the idea, Dunph and his friends head back to his house to pick up his bong. Dunph tries to get his wheelchair-using younger brother, Jackie (Tommy Bone), to smuggle it out of the house, but they are slowed down by Dunph's father Pat (Alec Baldwin), who insists that they all come inside and greet his poker-playing friends. While they are exchanging pleasantries, Jackie shows up with the bong wrapped in Dunph's jacket. The bong falls on the floor, and Pat picks it up asking what it is. Jackie tries to fool him by saying it is a horn..."a music horn". Pat's friend, Joey (George Wendt), asks Dunph to demonstrate his playing abilities. Dunph tries, but blows air, and Pat, having heard enough, lets them leave. Pat's friends all know what the device is, but choose not to inform on Dunph and his friends.
After "The Edge", Dunph and his friends get into a car (with him at the wheel) and drive off, with a big cloud of marijuana smoke fogging up the passenger compartment. Unable to see where he is going, Dunph rear-ends the back of a marked police car, with its occupant inside. Kaveech, one of Pat's poker-playing friends, has influence with a local judge, and manages to negotiate a plea to keep Dunph out of reform school. He is shipped off to Cornwall Academy, a Connecticut boys' boarding school with a segregated all-girls school nearby under the same name. As a condition of parole, Dunph must finish his senior year and graduate from Cornwall, or spend a year in jail. Though Dunph makes a sincere effort to stay out of trouble, it quickly catches up with him. The first incident is when Jack Wheeler (Gabriel Mann), a preppy blonde student who comes from an obviously privileged life, introduces Dunph to Billy Fu, a middle eastern exchange student with "the best reefer on campus". The trio fashions a bong out of a 55-gallon drum hidden in a large bush, and smokes about half a bag of marijuana. Dunph later learns that Billy Fu routinely misses classes and gets away with it, because his father promises to donate a large amount of money to the school, on condition that Billy graduates.
It does not take long for Dunphy to incur the wrath of Mr Funderburk (Timothy Crowe), his rigid dorm master, and Dean Bill Mort, who receives a letter simply addressed to the school, but meant for Dunph's eyes. The letter is from Drugs Delaney, revealing Dunph's hatred of the school and of Funderburk, who routinely assigns "work hours" to students who misbehave. Eventually, Dunph accumulates more work hours than he has class days. Dunph also manages to make friends with Jane Weston (Amy Smart), whom Wheeler calls "hands down, the coolest girl in school". The pair eventually develop their relationship from friendship to romance, but the relationship is brought to a screeching halt one day. This is the second part of an earlier incident when Dunph's room, shared by a boy named Irving (nicknamed Jizz by his classmates due to a masturbation-related prank), is raided by Funderburk. Wheeler's room is also raided.
The incident bringing Dunph's and Jane's relationship to a stop occurs when Dunph, Jane, Billy Fu, Jizz and Wheeler are in Dunph's room smoking marijuana with a bottle of alcohol present. Wheeler excuses himself to make a phone call. Moments later, Funderburk bursts into the room, catching everyone in the act of getting high and drunk. Funderburk orders Jane out of the room just as Wheeler shows up, innocently saying he was checking to see if anyone was studying. Funderburk orders him out as well. In the midst of a morality lecture on how he intends to turn everyone in as an incentive for them not to repeat such an incident in the future, Dunph stops Funderburk in mid-sentence, telling him to "shut the fuck up". Funderburk calls Dunph outside. Dunph reveals his knowledge of the deal with Billy Fu's father, and if Funderburk reports everyone but Billy, Dunph will in turn, report Billy. Funderburk counters by producing the marijuana he confiscated in the earlier raid. Dunph offers Funderburk a deal, he will let himself be expelled if everyone else gets work hours. Funderburk accepts.
When the boys are called to the Dean's office, they are surprised to learn that the only punishment was probation and work hours. Dunph eventually puts everything together and learns why: Funderburk gave him an even worse deal than they had worked out by having had Jane expelled from the school. Funderburk's actions also reversed her acceptance to Brown University the following year. Not long after, Dunph learns that Wheeler is accepted into Yale University by a letter of recommendation from Funderburk. Knowing that Wheeler was caught with marijuana during the first raid, Dunph concludes that Wheeler made his own deal with Funderburk to inform on everyone and have Jane expelled. Wheeler denies it, and Dunph threatens to throw Wheeler off the roof, where they are smoking marijuana one evening and Dunph reveals his knowledge of the situation. "Your life's gonna suck anyway," Dunph says to a visibly defeated and weak Wheeler. Dunph later makes his way into the Dean's office at Brown University, where he tells the Dean that he was the one responsible for Jane's expulsion from Cornwall, and that she was innocent of any wrongdoing. He convinces the Dean of Jane's innocence, which the Dean uses to influence the review board to overturn their decision to revoke Jane's admission.
The movie ends with Dunph graduating and even publicly defying Funderburk by refusing to shake his hand as customary at graduation, with his father and Jackie coming to school to pick him up. Dunph is given an acceptance letter from Rhode Island Junior College by his father. Dunph also reveals his intention to transfer to a "senior college...where people sleep over and shit."
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—John Ashbery (b. 1927)
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—Ralph Waldo Emerson (1803–1882)