Guest Stars Jeffrey DeMunn as Chuck Rhoades, Sr. Ben Shenkman as Ira Schirmer Rob Morrow as Adam DeGiulio Susan Misner as Terri McCue Frank Harts as Dale Christo Louisa Krause as Lou Clara Wong as Mistress Kate Arrington as Maria Saldana Kathryn Erbe as Roma Co Starring Daniel K. Isaac as Ben Kim Dan Soder as Dudley Mafee Ilfenesh Hadera as Deb Kawi Kaliswa Brewster as Shari Strang Marisa Brau-Reyes as Carrie (Babysitter) Sal Rendino as Hall's Associate Jenna DiMartini as Hot Twenty Something Yinka Adeboyeku as Driver Cliff Samara as Anil William Connell as Trader Terence Lorino as Bouncer Ashley Blankenship as Waitress Kyle Klaus as Other Trader