Guest Stars Mare Winningham as Diane Mallum Will Chase as Michael Friedman Phillipa Soo as Amber Collins Ray McKinnon as Jerry Mallum 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 Andrew Polk as Stephen Bark Susan Elaine Knight as TBD Co Starring Deadra Moore as Karen Johnson R. Keith Harris as Martin Willis WIlliam Flaman as Logan Parker Erin Dangler as Marianne Skolek Serena Ebhardt as Sue Ella Kobak Van Zee Annabelle Toomey as Thompson Brownlee Ray Dooley as Dr. Art Van Zee Cuyle Carvin as Pimp Jeff Campanella as Purdue Lawyer #4 Steven Reddington as Brownlee's Assistant Alpha Trivette as Judge Jones Abigail Jackson as Nan Goldin Olivia D. Dawson as Probation Officer Andrea Laing as TV Reporter Darryl Handy as Parent #2 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