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| Shawn Hatosy | Timothy Dunphy |
| Jon Abrahams | Drugs Delaney |
| Tommy Bone | Jackie Dunphy |
| Jonathan Brandis | Mousy |
| Jack Ferver | Irving Waltham |
| Adam LaVorgna | Tommy the Wire |
| Jesse Leach | Decenz |
| Gabriel Mann | Jack Wheeler |
| Kristen Shorten | Bunny Cote |
| Amy Smart | Jane Weston |
| Alex Toma | Billy Fu |
| Timothy Crowe | Mr. Funderberk |
| George Wendt | Joey |
| Alec Baldwin | Old Man Dunphy |
| Samantha Lavigne | Chaps |
| Chris Jewett | Brackett |
| George Martin | Dean Mort |
| Sean Gildea | Math Teacher |
| Bernie Sheredy | History Teacher |
| Robert Turano | Fram |
| Jimmy Landi | Ticket Taker |
| Amy Van Nostrand | Mrs. Winston |
| Mark O'Connell | Jizz Flashback Boy #1 |
| Seth Meier | Jizz Flashback Boy #2 |
| Nicholas Cardi | Cornhill Student #1 |
| Vincent Mesolella | Cornhill Student #2 |
| Joshua Moore | Cornhill Student #3 |
| Scott Rabideau | Cornhill Student #4 (Slater) |
| David Vaillancourt | Cornhill Student #5 (Crane) |
| Mike Cerrone | Cavwich |
In this coming-of-age comedy, Tim Dunphy is leading a go-nowhere existence, spending his days smoking pot and hanging out with his best friend, Drugs Delaney . But Tim's lazy days of getting high are jettisoned after a brush with the law convinces his blue-collar dad to send him to a Connecticut prep school. The one saving grace of the new school is Jane, a fellow student Tim falls for immediately.
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