Guest Stars Clark Gregg as Arthur Sackler, Sr. Sam Anderson as Raymond Sackler Brian Markinson as Howard Udell Jack Mulhern as Tyler Kryger Ron Lea as Bill Havens Ana Cruz Kayne as Brianna Ortiz Carolina Bartczak as Lily Kryger John Ales as Dr. Gregory Fitzgibbons Noah Harpster as Dr. Curtis Wright Tyler Ritter as John Brownlee John Murphy as Michael Friedman Johnny Sneed as Dr. Tim Cooper Matt Baram as Dr. Robert Kaiko Cody Porter as Dr. Paul Goldenheim Trenna Keating as Deborah Marlowe Stuart Hughes as Tony Joel Keller as Rick Mountcastle Austin Strugnell as Randy Ramseyer Maddy Hillis as Molly Dover Co Starring David Tompa as Conference Room Lawyer Darrin Baker as Dr. Hartman Laura Cilevitz as Richard's Secretary Natalia Gracious as Dr. Cooper's Receptionist Joy Kafi Pierre as Nurse Erin Megan Vincent as Carol Brewster Emidio Lopes as 7-11 Cashier Fuad Ahmed as Phil Megha Sandhu as Jenn Daniel Henkel as Young Raymond Lisa Auguste as Plushie Dancer #2 Brendan Stevenson as Dr. Cooper Protestor #1 David Kohlsmith as Young Richard Nabil Khatib as Pill Mill Security Guard Ingunn Omholt as Dr. Cooper Protestor #4 Cleve Schmalz as Guy at Pill Mill Tatiana Orlova as Dr. Cooper Protestor #5 Wayne Gwillim as Backstage Usher Cactus Simser as Cactus Maxine Adjeleian as Cheerleader #1 Eva Tzirtziganis as Cheerleader #2 Kirstie Cameron as Cheerleader #3 Nadia Barroso as Cheerleader #4 Sabrina Laplante as Cheerleader #5 Shaiann Roach as Cheerleader #6 Victoria Barrie as Cheerleader #7 Lindsay Aquin as Cheerleader #8 Gabriel Brito as Plushie Having Sex #2 Nicholas Fantauzzi as Plushie Having Sex #3 Erin Barkwell as Addict #1 Gustavo Valdez as Addict #2 Ashley Patitucci as Addict #3 Lily McEvenue as Plushie Dancer #4 Scott Edgecombe as Pawn Shop Owner Richard Brisco as Deborah's Doctor Zenna Davis-Jones as Other Connecticut Deputy Kalliane Brémault as Plushie Dancer #3 Kalie Hunter as Plushie Dancer #1 Scott Gerard as Pink Bartender Dustin Faith as Pool Waiter Tracy Baker as Sex with Plushie #1 Daniel J. Watts as Security Guard Barney Stacey Kay as Plushie Singer Ana Locherer as Dr. Cooper Protestor #3 Keanu Nunes as Plushie Having Sex #1 Mike Mitton as Pill Mill Older Doctor Jamie Mac as Connecticut Deputy #1 Watson Rose as Other Rep Malcolm Roberts as Security Guard Benji Stephanie Miller as Roller Rink Aide Anastassia Aksjonova as Woman in Bathroom Christopher Hong as Dr. Cooper Protestor #2