Guest Stars Mare Winningham as Diane Mallum Will Chase as Michael Friedman Ray McKinnon as Jerry Mallum Phillipa Soo as Amber Collins Brendan Patrick Connor as Howard Udell Raúl Esparza as Paul Mendelson Andrea Frankle as Beth Sackler Arischa Conner as Leah Turner Linda Powell as Karen Moles Rebecca Wisocky as Cynthia McCormick Aaron Serotsky as David Haddox Nicholas Logan as Walt Frank Wood as Doctor Trevor Long as Rudy Giuliani Co Starring R. Keith Harris as Martin Willis Morgan Brown as Gregg Wood Vince Pisani as David Gauvin Terrence Clowe as Cali Kire Elsasser as Lucas Kyle Findley as Rehab Resident #2 Ben Peck as Asa Hutchinson Tommy McNulty as Bro Rep Travis John Powers as Rehab Patient / Resident #1 Lowrey Brown as Rehab Counselor Annie Humphrey as Chemist Patrice Fisher as Methadone Clinic Nurse Rose Bianco as Therapist Parker Sack as Dirk David Alexander as Jay McCloskey Shelly Townsend as Vivian Charles Green as Betsy's Pastor Rabon Hutcherson II as Purdue Rep #1 Athena McDowell as DEA Lab Analyst Ja'Corey Jones as Rehab Resident #3 Jay Thompson as Kentucky Pharmacist Joe Knezevich as Matt Erickson
