Jessalyn Gilsig Actor Chi McBride Principal Steven Harper Actor Fyvush Finkel Harvey Lipshultz Actor Anthony Heald Vice Principal Scott Guber Actor Joey Slotnick Actor Tom McCarthy Actor Sharon Leal Marylin Sudor Actor Nicky Katt Actor Loretta Devine Marla Hendricks Actor Rashida Jones Actor Daniel Kountz Guest Star Gregg Henry Guest Star Bianca Kajlich Guest Star Mike Pniewski Guest Star Chris Evans Guest Star David E. Kelley Executive Producer