Special Guest Stars Charles Grodin as Brett Forrester Guest Stars Raúl Esparza as Rafael Barba Elizabeth Marvel as Counselor Rita Calhoun Marissa Matrone as Judge Maria Ana DeFeceo Brooke Hoover as Toni Apriel Starkweather as Young Woman Anthony Rapp as Nathan Elliott Gould as Walter Tompkins Jeremy Bobb as Vincent Moran Marc Webster as Damon Tijuana Ricks as Principal Buck Henry as Morton Frank Wood as Andrew Lennox Karen Shallo as Rose Matthews Jayce Bartok as Eli Fromson Robert Sella as Tompkins Former Student Alvin Epstein as Harold Lassiter Mason Pettit as Curt Brian Faherty as Frank Uncredited Steve Zirnkilton voices Opening Narration