Guest Stars Asia Kate Dillon as Taylor Mason Kelly AuCoin as "Dollar" Bill Stearn Dan Soder as Dudley Mafee Glenn Fleshler as Orrin Bach Allan Havey as Karl Allerd Keith Eric Chappelle as Everett Wright Ilfenesh Hadera as Deb Kawi Jack Gore as Gordie Axelrod Danny Strong as Todd Krakow Zachary Unger as Kevin Rhoades Christopher Denham as Oliver Dake Malachi Weir as Lonnie Watley Eric Bogosian as Lawrence Boyd Jerry O'Connell as Steven Birch Erinn Ruth as Mo Shaunette Renée Wilson as Stephanie Reed Marc Kudisch as Dr. Lenny Gustaferson Dennis Boutsikaris as Kenneth Malverne Ritchie Coster as Donald Thayer Shannon Koob as Marriage Counselor Ross Partridge as Tom McKinnon Tammy Blanchard as Judo Partner Jake Robards as Michael Arendt Mike Starr as Nicky Pawlowski Carolyn McCormick as Banker Julee Cerda as Sam Brandt Co Starring Daniel K. Isaac as Ben Kim Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Alexa Jacqueline Swinton as Eva Rhoades Timothy Davis as Chef Ryan Ellen Adair as Graff Lucas Calhoun as Ferguson Sean Ringgold as Security Guard Jabari Gray as FBI Agent John Danaher as Instructor Angela Marie Roy as Shayleen McKinnon David Neal Levin as Clarence Fiedler David Chang as Himself Richard DeDomenico as Custom Tailor Faron Salisbury as Early 40s Prick Kabe Park as Sung Brian Faherty as American Manager Suzanne Johnson as Linda Boyd Brian Distance as Home Aide Katlyn Carlson as Bonnie Edward Murphy Kelahan as Phillip Carroll Alexandra Wilson as Segment Producer