Guest Stars Asia Kate Dillon as Taylor Mason Kelly AuCoin as "Dollar" Bill Stearn Jeffrey DeMunn as Chuck Rhoades, Sr. Dan Soder as Dudley Mafee Ben Shenkman as Ira Schirmer Ilfenesh Hadera as Deb Kawi Matt Servitto as Bob Sweeney David Strathairn as Jack Foley Daniel Cosgrove as Dan Margolis Shaunette Renée Wilson as Stephanie Reed Marc Kudisch as Dr. Lenny Gustaferson Scott Aiello as Tommy Barkow Jason Babinsky as Theo Tammy Blanchard as Judo Partner Ben Folds as Himself Kristina Cole as Martha Ken Marks as Roger Murray Co Starring Daniel K. Isaac as Ben Kim Kira Visser as Donna Zina Wilde as Helena Frank Bowman as Abraham Jose Guns Alves as Delivery Man Hunter Canning as Desk Jockey Brian Patrick Murphy as A.R. Juan Luis Acevedo as Domingo
