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