A prequel to the critically acclaimed series featuring Jerri Blank, a 46 year old ex-junkie, ex-con who returns to high school in a bid to start her life over.
| Actor | Role |
|---|---|
 Amy SedarisJerri Blank | Jerri Blank |
 Stephen ColbertChuck Noblet | Chuck Noblet |
 Paul DinelloGeoffrey Jellineck | Geoffrey Jellineck |
 Greg HollimonPrincipal Blackman (as Gregory Holliman) | Principal Blackman (as Gregory Holliman) |
 Philip Seymour HoffmanHenry | Henry |
 Ian HolmDr. Putney | Dr. Putney |
 Chandra WilsonInmate | Inmate |
 Deborah RushSara Blank | Sara Blank |
 Dan HedayaGuy Blank | Guy Blank |
 Joseph CrossDerrick Blank | Derrick Blank |
 Elisabeth HarnoisMonica | Monica |
 Alexis DzienaMelissa | Melissa |
 Carlo AlbanMegawatti | Megawatti |
 Allison JanneyAlice | Alice |
| DDolores DuffyIris Puffybush | Iris Puffybush |
 Maria ThayerTammi Littlenut | Tammi Littlenut |
 Sarah Jessica ParkerPeggy Callas | Peggy Callas |
 Matthew BroderickRoger Beekman | Roger Beekman |
 Chris PrattBrason | Brason |
 Justin TherouxCarlo Honklin | Carlo Honklin |
 Kristen JohnstonCoach Divers | Coach Divers |
| SSarah ThyreCoach Wolf | Coach Wolf |
 Ryan DonowhoStanley (uncredited) | Stanley (uncredited) |
| WWallace LittleTrace | Trace |
 David PasquesiStew | Stew |
 Christopher LarkinKim (uncredited) | Kim (uncredited) |