Guest Stars Will Chase as Michael Friedman Mare Winningham as Diane Mallum Phillipa Soo as Amber Collins Ray McKinnon as Jerry Mallum Ian Unterman as Jonathan Sackler Brendan Patrick Connor as Howard Udell Raúl Esparza as Paul Mendelson Andrea Frankle as Beth Sackler Lawrence Arancio as Raymond Sackler Jaime Ray Newman as Kathe Sackler Jake McDorman as John Brownlee Cleopatra Coleman as Grace Pell Winsome Brown as Theresa Sackler Walter Bobbie as Mortimer Sackler Alan Campbell as Dr. Paul Goldenheim Linda Powell as Karen Moles Rebecca Wisocky as Cynthia McCormick Kenneth Tigar as Arthur Sackler Meagen Fay as Sister Beth Davies Adam Grupper as Purdue Lawyer Amy Rutberg as Alice Fisher Brian Keane as Curtis Wright Co Starring Deadra Moore as Karen Johnson R. Keith Harris as Martin Willis Andres Erickson as Mortimer D.A. Sackler Alayna Hester as Elizabeth Ann McClung Morgan Brown as Gregg Wood Deja Dee as Stephanie Mountcastle Vince Pisani as David Gauvin Paden Fallis as Louis Melton Anthony Reynolds as Sheriff Travis Smith as Eric Miller Ray Dooley as Dr. Art Van Zee Serena Ebhardt as Sue Ella Kobak Van Zee Cory Scott Allen as Tim Kenny Alfonso as Medical Board Administrator Michael Silberblatt as Drug User at Bridge Nicole Burgess as New Sales Rep Mark Cabus as Senator Kefauver Jon Hayden as Senator Chris Dodd Mary Kraft as Dr. Deborah Leiderman Christie Duke as Receptionist Taylor Simmons as Drug User at House