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 Malachi Weir as Lonnie Watley Christopher Denham as Oliver Dake Eric Bogosian as Lawrence Boyd Jerry O'Connell as Steven Birch Shaunette Renée Wilson as Stephanie Reed Erinn Ruth as Mo Marc Kudisch as Dr. Lenny Gustaferson Dennis Boutsikaris as Kenneth Malverne Ritchie Coster as Donald Thayer Ross Partridge as Tom McKinnon Shannon Koob as Marriage Counselor Jake Robards as Michael Arendt Tammy Blanchard as Judo Partner Carolyn McCormick as Banker Mike Starr as Nicky Pawlowski Julee Cerda as Sam Brandt Co Starring Daniel K. Isaac as Ben Kim Kira Visser as Donna Zina Wilde as Helena 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 David Neal Levin as Clarence Fiedler Angela Marie Roy as Shayleen McKinnon Kabe Park as Sung Brian Distance as Home Aide Katlyn Carlson as Bonnie Brian Faherty as American Manager David Chang as Himself Richard DeDomenico as Custom Tailor Faron Salisbury as Early 40s Prick Suzanne Johnson as Linda Boyd Edward Murphy Kelahan as Phillip Carroll Alexandra Wilson as Segment Producer