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 Shaunette Renée Wilson as Stephanie Reed Daniel Cosgrove as Dan Margolis Marc Kudisch as Dr. Lenny Gustaferson Scott Aiello as Tommy Barkow Tammy Blanchard as Judo Partner Jason Babinsky as Theo Kristina Cole as Martha Ken Marks as Roger Murray Ben Folds as Himself Co Starring Daniel K. Isaac as Ben Kim Zina Wilde as Helena Kira Visser as Donna 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