Guest Stars Mare Winningham as Diane Mallum Will Chase as Michael Friedman 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 Ben Peck as Asa Hutchinson David Alexander as Jay McCloskey Kyle Findley as Rehab Resident #2 Rabon Hutcherson II as Purdue Rep #1 Lowrey Brown as Rehab Counselor Patrice Fisher as Methadone Clinic Nurse Rose Bianco as Therapist Ja'Corey Jones as Rehab Resident #3 Travis John Powers as Rehab Patient / Resident #1 Jay Thompson as Kentucky Pharmacist Athena McDowell as DEA Lab Analyst Tommy McNulty as Bro Rep Shelly Townsend as Vivian Parker Sack as Dirk Charles Green as Betsy's Pastor Annie Humphrey as Chemist Joe Knezevich as Matt Erickson
