Guest Stars David Paymer as Rueben Bauer Peter Coyote as James Alan Pierce Brooke Nevin as Shelby Coulson Joanna Cassidy as Ruby Josh Braaten as Derek Shelton Jim Garrity as Detective Malone James Madio as Officer Timmy Russo Jude Ciccolella as Imaginary Detective Chris Tardio as Detective Gomez Darin Heames as Lomax Gareth Williams as Brian McGrath Max Decker as Pete Clifford Morts as Judge Horford Michael Bunin as Kevin Gillespie Co Starring Bruno Oliver as Prison Guard Stephen Jordan as Prosecutor Larkin Campbell as Desk Officer James Thomas Gilbert as Defendant Ryan Dooley Cleo Anthony as Court Clerk