Guest Stars Jeffrey DeMunn as Chuck Rhoades, Sr. Stephen Kunken as Ari Spyros Glenn Fleshler as Orrin Bach Susan Misner as Terri McCue Arthur Nascarella as Bruno Capparelo David Cromer as Donnie Caan Louisa Krause as Lou Scott Cohen as Pete Decker Kate Arrington as Maria Saldana Annapurna Sriram as Tara Mohr Austin Pendleton as Albus Melissa Errico as June Raichlein Tamara Tunie as Amelia Kate Jennings Grant as Evelyn Benson Jeremy Bobb as Hutch Bailey III John Henry Cox as Jerome Purkheiser Mark Gessner as Jacobsen Co Starring Daniel K. Isaac as Ben Kim Kelly AuCoin as "Dollar" Bill Stearn Ilfenesh Hadera as Deb Kawi Malachi Weir as Lonnie Watley Frank Harts as Dale Christo Kaliswa Brewster as Shari Strang Catherine A. Callahan as Lilly Smith Philip Hoffman as Lawyer Susan Kelechi Watson as Wilma "Billie" Keen Nicholas J. Coleman as Mark Jessica Rush as Christine Jose Soto as Basilio Bustamante Jessica Keenan Wynn as Cheryl Richard Toth as Elder Board Member Bobby Kruger as Lifson Scott C. Robertson as Board Member Cameron Colley as Boy Decker Paige Fitzgerald as Girl Decker Graig Guggenheim as Umpire