Guest Stars Rebecca Pidgeon as Charlotte Canning Ryan Bre Blair as Joss Morgan Benito Martinez as Benjamin Castillo Hugh Fitzgerald as Cartwright Barry Corbin as Carson Sandy Martin as Woman with Cane Lori Lively as Tom Ryan's Mother Dayton Callie as Middle Aged Man Natalie Avital as The young Girl Barbara Perry as Old Woman Silvia McClure as Reception Nurse Maz Siam as Prosperous Fellow Azdine Melliti as Fierst Bodyguard Jackson Fox as 9 Year-old Tom Ryan Mary Eileen O'Donnell as Nurse Scott Barry as Man with Dog Caleb Steinmeyer as 15 / 19 Year-old Tom Ryan Eric L. Haney as Recruiting Sergeant Kevin Fry as Tom Ryan's Stepfather Jack Betts as Old Priest Nigel Gibbs as General Hayes