Guest Stars Clark Gregg as Arthur Sackler, Sr. Sam Anderson as Raymond Sackler Brian Markinson as Howard Udell Jack Mulhern as Tyler Kryger 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 John Murphy as Michael Friedman Matt Baram as Dr. Robert Kaiko Johnny Sneed as Dr. Tim Cooper Cody Porter as Dr. Paul Goldenheim Trenna Keating as Deborah Marlowe Yanna McIntosh as ER Doctor Co Starring Olivia Markowski as Toddler Kaylee Vivienne Markowski as Toddler Kaylee David Tompa as Conference Room Lawyer Darrin Baker as Dr. Hartman Laura Cilevitz as Richard's Secretary Jamaal Grant as Shawn Flowers Natalia Gracious as Dr. Cooper's Receptionist Joy Kafi Pierre as Nurse Erin Tara Samuel as Diane Shnitzler Laura Afelskie as Jess Brewster Megha Sandhu as Jenn Kyle Gatehouse as Riggs Fuad Ahmed as Phil Helen Taylor as Joan Pharmacist Billy Smith as Sheriff Wayne Julia Lalonde as Becky Sivaswamy Iver as Conference Doctor #3 Jessie Faye Lavin as Tango Dancer Woman Bryant Robert Lopez as Tango Dancer Man Thomas Richards as Tuba Player #1 Irina Harel as Conference Doctor #8 Renee Ziegenfuss as Conference Doctor #7 Bruce Harrott as Conference Doctor #6 Mario Araya as Conference Doctor #5 Svetlana Bolter as Conference Doctor #4 Alison J. Palmer as Janet John Hrajnik as Conference Doctor #2 Deborah Izzo as Conference Doctor #1 Seth Drabinsky as Macaroni Waiter Carly Street as Dr. Lorraine Sullivan Michelle Fisk as Coroner Tina Allan Dobrescu as Scraggly Guy Paul Aihoshi as UPS Guy