Guest Stars Carolina Bartczak as Lily Kryger Jack Mulhern as Tyler Kryger Brian Markinson as Howard Udell Clark Gregg as Arthur Sackler, Sr. Sam Anderson as Raymond Sackler Ana Cruz Kayne as Brianna Ortiz Ron Lea as Bill Havens John Ales as Dr. Gregory Fitzgibbons Noah Harpster as Dr. Curtis Wright Tyler Ritter as John Brownlee Johnny Sneed as Dr. Tim Cooper John Murphy as Michael Friedman 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 Megan Vincent as Carol Brewster Kafi Pierre as Nurse Erin Natalia Gracious as Dr. Cooper's Receptionist Joy Fuad Ahmed as Phil Emidio Lopes as 7-11 Cashier Megha Sandhu as Jenn Daniel J. Watts as Security Guard Barney Brendan Stevenson as Dr. Cooper Protestor #1 Lisa Auguste as Plushie Dancer #2 Nabil Khatib as Pill Mill Security Guard Tatiana Orlova as Dr. Cooper Protestor #5 Wayne Gwillim as Backstage Usher Ingunn Omholt as Dr. Cooper Protestor #4 Cleve Schmalz as Guy at Pill Mill Cactus Simser as Cactus Maxine Adjeleian as Cheerleader #1 Eva Tzirtziganis as Cheerleader #2 Ana Locherer as Dr. Cooper Protestor #3 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 Kalie Hunter as Plushie Dancer #1 Jamie Mac as Connecticut Deputy #1 Scott Edgecombe as Pawn Shop Owner Daniel Henkel as Young Raymond 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 Kalliane Brémault as Plushie Dancer #3 Christopher Hong as Dr. Cooper Protestor #2 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 Anastassia Aksjonova as Woman in Bathroom