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| Freddie Prinze Jr. | Zach Siler |
| Rachael Leigh Cook | Laney Boggs |
| Matthew Lillard | Brock Hudson |
| Paul Walker | Dean Sampson |
| Jodi Lyn O'Keefe | Taylor Vaughan |
| Kevin Pollak | Wayne Boggs |
| Anna Paquin | Mackenzie Siler |
| Kieran Culkin | Simon Boggs |
| Elden Henson | Jesse Jackson |
| Usher Raymond | Campus DJ |
| Kimberly ''Lil' Kim'' Jones | Alex |
| Gabrielle Union | Katie |
| Dulé Hill | Preston |
| Tamara Mello | Chandler |
| Tim Matheson | Harlan Siler |
| Clea DuVall | Misty |
| Jarrett Lennon | Naylon |
| Chris Owen | Derek Funkhouser Rutley |
High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson . Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.
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