Special Guest Stars Rosie O'Donnell as Judge Madeline Summers Guest Stars Ben Feldman as Fred Brooke D'Orsay as Deborah "Deb" Dobkins Gabriel Olds as Simon Dewey / Jake Garner Ron Clinton Smith as Richie Sagansky Robert Herrick as Ken Hall Chuck Woolery as Dream Judge / Host Steven Barnes as Gary Monroe Mark Wilson as Attorney Steve Browers Dekori Trevon Robinson as Michael Mason Co Starring Gregory Alan Williams as Judge Warren Libby Melissa Ponzio as Selette Garner Charlotte Haynes Hazzard as Angie Mason Caroline McKinley as Dr. Lois Farrar