Guest Stars Rex Linn as Detective Frank Tripp Sofia Milos as Detective Yelina Salas Michael Whaley as Detective Bernstein Aaron Paul as Ben Gordon Dayton Callie as Adams - Parole Officer Rena Sofer as Alison Eric Ladin as Jeff Wilton Chris Penn as Pete Wilton Whip Hubley as Nick Gordon Co Starring Hayden Tank as Raymond Caine, Jr. Tasia Sherel as DAN Tech Robert Alan Beuth as Principal Roland Chad Gordon as Mark Hubbard