Guest Stars Will Chase as Michael Friedman Mare Winningham as Diane Mallum Phillipa Soo as Amber Collins Ray McKinnon as Jerry Mallum Brendan Patrick Connor as Howard Udell Raúl Esparza as Paul Mendelson Arischa Conner as Leah Turner Andrea Frankle as Beth Sackler 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 Kire Elsasser as Lucas Terrence Clowe as Cali Patrice Fisher as Methadone Clinic Nurse Annie Humphrey as Chemist Rose Bianco as Therapist Kyle Findley as Rehab Resident #2 Athena McDowell as DEA Lab Analyst Lowrey Brown as Rehab Counselor Ja'Corey Jones as Rehab Resident #3 Jay Thompson as Kentucky Pharmacist Travis John Powers as Rehab Patient / Resident #1 Rabon Hutcherson II as Purdue Rep #1 Tommy McNulty as Bro Rep Ben Peck as Asa Hutchinson Shelly Townsend as Vivian Parker Sack as Dirk David Alexander as Jay McCloskey Charles Green as Betsy's Pastor Joe Knezevich as Matt Erickson
