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| Heath Ledger | Patrick 'Pat' Verona |
| Julia Stiles | Katarina 'Kat' Stratford |
| Joseph Gordon-Levitt | Cameron James |
| Larisa Oleynik | Bianca Stratford |
| David Krumholtz | Michael Eckman |
| Andrew Keegan | Joey Donner |
| Susan May Pratt | Mandella |
| Gabrielle Union | Chastity |
| Larry Miller | Mr. Walter Stratford |
| Daryl Mitchell | Mr. Morgan |
| Allison Janney | Ms. Perky |
| David Leisure | Mr. Chapin |
| Cameron Fraser | Trevor |
| Eric Reidman | Audio Visual Guy |
| Quinn Maixner | Beautiful Jock |
| Demegio Kimbrough | Coffee Kid #1 |
| Todd Butler | Coffee Kid #2 |
| Gil Junger | Teacher (uncredited) |
| Dennis Mosley | Cohort |
| Nick Vukelic | Drugged Out Loser |
| Bianca Kajlich | Coffee Girl |
| Alisa Mackay | Coffee Girl #2 (uncredited) |
| Benjamin Laurence | Wimpy Loser |
| Aidan Kennedy | Laughing Loser |
| Jesse Dyer | Screaming Loser |
| Jelani Quinn | Crying Loser |
| Joshua Thorpe | Jock |
| Tarance Houston | Derek |
A pretty, popular student can't date until her rebellious older sister gets a suitor of her own.
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