Guest Stars Anthony Edwards as Alan Reed Gabriel Sloyer as Gabriel Calatrava Ben Rappaport as Billy McFarland K.K. Moggie as Banker India Ennenga as Julia Reed Tracy Pollan as Sherry Reed James Waterston as Squash Partner Co Starring Chris Cafero as David Morrison Richie Herschenfeld as Richie Notar Winslow Bright as Jenny Whitley Jason Schuchman as Lavin Niraj Arjan as Gavin Peterson Austin Ku as Michael Xufu Huang Nicholas Calhoun as Reggie Walsh Cristala Carter as Female Suit Ben Beckley as Male Suit Esco Jouléy as Kehinde Max Chernin as Hipster Migs Govea as Yakub Matthews Mary Jo Mecca as Housekeeper Michael Zegarski as Attendant Tony Neil Butler as Squash Attendant Justin Ariola as Security Guard Nurit Monacelli as Lawyer Amelia Hammer Harris as Sade Lawrence Ballard as Jaffe Usama Siddiquee as Ron Wheaton Alex Bartner as Mark Nikka Graff Lanzarone as Blaine Desi Domo as Alison Nick Ong as Admin Alex Weisman as Alan's Assistant