Timothy "Dildo/Dunph" Dunphy (Shawn Hatosy), is in the Class of 1974 in his high school senior year living in Pawtucket, Rhode Island, comes from a troubled single parent working-class family, and is friends with those that have aspirations which do not exceed smoking marijuana at the water tower that has a view of the town. His father, Pat (Alec Baldwin), suffers from his wife committing suicide and appears naïve when the boys come back to the Dunphy's house to get a bong. A regularly held poker game is in progress. Pat insists that the boys be respectful and come in to say hello. The boys' intention is undetected by Pat that they are using drugs when Dunph's wheelchair-using younger brother, Jackie (Tommy Bone), attempts to hand off the bong wrapped in Dunph's coat. It falls to the floor. Jackie suggests that it is a musical horn which Pat's friend, Joey (George Wendt), asks Dunph to demonstrate, only able to make sounds about which Pat is dismissive. Pat's friends chuckle at Pat's reaction. Off the boys go on their adventures.
The guys head home with Dunph at the wheel but he is unable to see the road with the cloud of marijuana smoke filling the cab. He rear-ends a police vehicle. Pat's poker game player, Caveech, uses his influence with a local judge to replace a reform school sentence with the stipulation of parole graduating high school at Cornwall Academy, a Connecticut boys' boarding school with a sister school nearby under the same name. Failure to graduate vacates the terms of parole and he will serve a one year jail sentence.
He meets the rigid dorm master, Mr. Funderburk (Timothy Crowe), who emphases learning the school rules book. Dunph learns that new friend Wheeler and other new schoolmates, a class of people that seem to have more opportunities than himself, are involved in their own mischief just like the boys back home. Billy Fu is one particular example. He is a middle eastern exchange student with "the best reefer on campus". He routinely misses classes without repercussion because his father pledges a large donation to the school on the condition that Billy graduate.
Dunph is no longer just any student at the school when "Drugs" Delaney (Jon Abrahams), writes Dunph with his particular colorful words and addressing the letter in the most simplest of ways that the school has to open it to learn of the contents; Dunph has low regard for both the school and Mr. Funderburk. Dunph routinely gets sanctioned with work hours as punishment for his school rules transgressions. He also develops a friendship with a sister school student, Jane Weston (Amy Smart), regarded as "hands down, the coolest girl in school". A romance develops and through her advice he learns about personal fulfillment which could be achieved by an education.
She and others are found out by Mr. Funderburk smoking marijuana and drinking alcohol in a dorm room of the boys' dorm. The incident is resolved, unknown to Dunph's knowledge until too late, with Jane expelled for school rules violations. Dunph feels responsible for dashing Jane's goal of attending Brown University following graduation. He concludes: Wheeler's acceptance at Yale University is weighed heavily by a letter of recommendation from Funderburk and Wheeler was caught with marijuana during an earlier raid; therefore Wheeler made his own deal with Funderburk to inform on others which resulted in Jane being expelled. Dunph resolves to see Jane's college plans revitalized by speaking with the Dean at Brown University, as he explains that she was the innocent party in the incident.
Dunph comes to terms with his father's apprehension discussing the death in the family because the latter felt responsible for imposing on her a life that she could not handle; she being too young when they married, depressed and agoraphobic. Dunph refuse to shake Funderburk's hand at the graduation ceremony in the auditorium and exits after asking his classmates for his "luggage". He then meets up with his father and Jackie as they arrive. Pat hands over an acceptance letter from the Rhode Island Junior College where Dunph points out that everyone is accepted although he could then transfer to a "senior college...where people sleep over and shit." Pat congratulates Dunph for being the first of the family to go to college and the younger brother not to be trumped surmises the possibility that it just very well may be that Jackie himself may be the first to graduate.
An alternate ending is found on the DVD, which has Dunph leaving the graduation ceremonies, meeting Jackie and Clopsy, their three-legged dog. Also showing up is Jane, whom Dunph shares a passionate kiss with, which annoys Funderburk, who wastes no time in rebuking both Dunph and Jane. Dunph responds by punching Funderburk, knocking him to the sidewalk.Shawn Hatosy as Timothy "Dildo/Dunph" Dunphy
Amy Smart as Jane Weston
Alec Baldwin as Old Man Dunphy
Jon Abrahams as Drugs Delaney
Jonathan Brandis as Mousy
Adam LaVorgna as Tommy the Wire
Jesse Leach as Decenz
Gabriel Mann as Jack Wheeler
Jack Ferver as Irving "Jizz" Waltham
Richard Jenkins as Barney
Mike Cerrone as Caveech
George Wendt as Joey
Eric Brown as English teacher
Timothy Crowe as Mr. Funderburk
The exterior prep school scenes were filmed at the University of Rhode Island, with interior scenes filmed in the Cranston Street Armory in the west end of Providence. The Brother Adelard Ice Hockey Arena at Mount Saint Charles Academy was used for a brief scene.USA 16 August 1999 (Warwick, Rhode Island) (premiere)
USA 1 September 1999
Iceland 8 October 1999
Australia 28 October 1999
Netherlands 28 October 1999
Sweden 3 December 1999
Finland: 2000 (DVD premiere). Titled: "Elämää oppimassa"
Belgium 5 January 2000
Norway 18 February 2000
Argentina: 22 February 2000 (video premiere). Titled: "Lejos de Providencia".
Spain: 30 June 2000. Titled: "No puedo perderte por algo tan tonto como el sexo"
Slovenia 24 August 2000
Hungary: 17 October 2000 (video premiere). Titled: "Jótanácsok kamaszoknak"
Brazil: Deixa Rolar
France: Les années lycée
Greece (TV title): Anexigiti pronoia
Greece (video title): O eparhiotis
Italy: Outside Providence
The film recouped costs within the first month of release, with revenue exceeding the $7 million budget by $300,000.
Rotten Tomatoes gives the film a score of 50% based on 74 reviews.