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 Louis Cancelmi as Victor Mateo Ben Shenkman as Ira Schirmer Terry Kinney as Hall Keith Eric Chappelle as Everett Wright Ilfenesh Hadera as Deb Kawi Malachi Weir as Lonnie Watley Jack Gilpin as Sean Ayles David Strathairn as Jack Foley Shaunette Renée Wilson as Stephanie Reed Ritchie Coster as Donald Thayer Co Starring Daniel K. Isaac as Ben Kim Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Tijuana Ricks as Tonelle "T" Burton Ellen Adair as Graff Lucas Calhoun as Ferguson Frank Bowman as Abraham Ross DeGraw as Mayor Julia Brothers as Crowd Member Margot Avery as Council Member Southside Johnny & The Asbury Jukes as Themselves Uncredited Scott Mena as Party Guest