Cast and Characters
| Actor | Character | Seasons | Role |
|---|---|---|---|
| Chi McBride | Steven Harper | 1–4 | Principal |
| Anthony Heald | Scott Guber | 1–4 | Vice Principal |
| Jessalyn Gilsig | Lauren Davis | 1–2 | Social Studies teacher; left Winslow to teach at a private school |
| Nicky Katt | Harry Senate | 1–3 (episodes 1–49) | Teacher of "the Dungeon"; quit in episode 49 |
| Loretta Devine | Marla Hendricks | 1–4 | Social Studies teacher |
| Sharon Leal | Marylin Sudor | 1–4 | English teacher and music instructor |
| Fyvush Finkel | Harvey Lipschultz | 1–4 | History teacher |
| Rashida Jones | Louisa Fenn | 1–2 | Secretary |
| Thomas McCarthy | Kevin Riley | 1 (episodes 1–13; special guest appearance in episode 18) | Football coach; fired in episode 13 |
| Joey Slotnick | Milton Buttle | 1 (episodes 1–13; special guest appearance in episode 15) | English teacher; fired in episode 13 |
| Kathy Baker | Meredith Peters | 1–2; recurring in season 1 | Teacher |
| Jeri Ryan | Ronnie Cooke | 2–4 | Teacher; assistant vice principal (end of season 3); guidance counselor (season 4) |
| Michael Rapaport | Danny Hanson | 2–4 | Teacher |
| China Jesushita Shavers | Brooke Harper | 2–3; recurring in season 2 | Student |
| Jon Abrahams | Zach Fischer | 3 | Physics teacher |
| Joey McIntyre | Colin Flynn | 3 | English Teacher |
| Michelle Monaghan | Kimberly Woods | 3 (episodes 49–57; not featured in opening credits but receives "also starring" billing) | Teacher; transferred to a school in another state to avoid a dangerous, obsessed student in episode 57 |
| Cara DeLizia | Marcie Kendall | 3 (not featured in opening credits but receives "also starring" billing) | Principal's assistant and student |
| Natalia Baron | Carmen Torres | 4 | Physics teacher |
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