Guest Stars Will Chase as Michael Friedman Mare Winningham as Diane Mallum Ray McKinnon as Jerry Mallum Phillipa Soo as Amber Collins Ian Unterman as Jonathan Sackler Brendan Patrick Connor as Howard Udell Lawrence Arancio as Raymond Sackler Arischa Conner as Leah Turner Jake McDorman as John Brownlee Alan Campbell as Dr. Paul Goldenheim Alayna Hester as Elizabeth Ann McClung Aaron Serotsky as David Haddox Meagen Fay as Sister Beth Davies Adam Grupper as Purdue Lawyer Susan Elaine Knight as TBD Andrew Polk as Stephen Bark Co Starring Deadra Moore as Karen Johnson R. Keith Harris as Martin Willis WIlliam Flaman as Logan Parker Ray Dooley as Dr. Art Van Zee Annabelle Toomey as Thompson Brownlee Erin Dangler as Marianne Skolek Serena Ebhardt as Sue Ella Kobak Van Zee Steven Reddington as Brownlee's Assistant Abigail Jackson as Nan Goldin Alpha Trivette as Judge Jones Cuyle Carvin as Pimp Jeff Campanella as Purdue Lawyer #4 Andrea Laing as TV Reporter Darryl Handy as Parent #2 Olivia D. Dawson as Probation Officer Maggie Toomey as Thompson Brownlee (Age 7) Maura Mazurowski as Prostitute Yinka Olagbegi as Purdue Security Eliana Ghen as Brownlee Reporter Jasmine Shea as Kaitlyn Cutler Dustin Lewis as Parent #1 Brian Kurlander as Purdue Lawyer #3