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| D. J. Qualls | Dizzy |
| Eliza Dushku | Danielle |
| Zooey Deschanel | Nora |
| Lyle Lovett | Bear |
| Jerod Mixon | Kirk |
| Illeana Douglas | Kiki Pierce |
| Parry Shen | Glen |
| Kurt Fuller | Mr. Undine |
| Julius Carry | Coach |
| M. C. Gainey | Clem |
| Eddie Griffin | Luther |
| Sunny Mabrey | Courtney |
| Ross Patterson | Conner |
| Matt Gogin | Ed Ligget |
| Horatio Sanz | Dance Instructor |
| Tony Hawk | Himself |
| Jerry O'Connell | Highland High Party Twin #1 |
| Charlie O'Connell | Charlie |
| Gene Simmons | Reverend |
| Tommy Lee | Himself |
| Kool Mo Dee | Ted |
| Jermaine D. Maudlin | Jermaine |
| Josh Todd | Rudy |
| Vanilla Ice | Music Store Employee |
| Henry Rollins | Warden |
| David Hasselhoff | Himself |
In jail, a teenager meets another inmate who shows him how to act cool at his high school.
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