Guest Stars Clark Gregg as Arthur Sackler, Sr. Sam Anderson as Raymond Sackler Jack Mulhern as Tyler Kryger Brian Markinson as Howard Udell Ana Cruz Kayne as Brianna Ortiz Ron Lea as Bill Havens Carolina Bartczak as Lily Kryger John Ales as Dr. Gregory Fitzgibbons Noah Harpster as Dr. Curtis Wright Tyler Ritter as John Brownlee Matt Baram as Dr. Robert Kaiko Johnny Sneed as Dr. Tim Cooper John Murphy as Michael Friedman 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 Kafi Pierre as Nurse Erin Natalia Gracious as Dr. Cooper's Receptionist Joy Megan Vincent as Carol Brewster Fuad Ahmed as Phil Emidio Lopes as 7-11 Cashier Megha Sandhu as Jenn Nabil Khatib as Pill Mill Security Guard Brendan Stevenson as Dr. Cooper Protestor #1 Lisa Auguste as Plushie Dancer #2 Tatiana Orlova as Dr. Cooper Protestor #5 Ingunn Omholt as Dr. Cooper Protestor #4 Ana Locherer as Dr. Cooper Protestor #3 Wayne Gwillim as Backstage Usher Cleve Schmalz as Guy at Pill Mill Cactus Simser as Cactus Maxine Adjeleian as Cheerleader #1 Eva Tzirtziganis as Cheerleader #2 Christopher Hong as Dr. Cooper Protestor #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 Kalliane Brémault as Plushie Dancer #3 Jamie Mac as Connecticut Deputy #1 Scott Edgecombe as Pawn Shop Owner Daniel Henkel as Young Raymond Daniel J. Watts as Security Guard Barney Dustin Faith as Pool Waiter Zenna Davis-Jones as Other Connecticut Deputy Lily McEvenue as Plushie Dancer #4 Richard Brisco as Deborah's Doctor David Kohlsmith as Young Richard Anastassia Aksjonova as Woman in Bathroom Kalie Hunter as Plushie Dancer #1 Scott Gerard as Pink Bartender Tracy Baker as Sex with Plushie #1 Stacey Kay as Plushie Singer Keanu Nunes as Plushie Having Sex #1 Mike Mitton as Pill Mill Older Doctor Watson Rose as Other Rep Malcolm Roberts as Security Guard Benji Stephanie Miller as Roller Rink Aide