Guest Stars Bailey De Young as Imogene Cleary John Scurti as Nicky Emily Bergl as Tessie Erik Palladino as Frank Austin Basis as Alvin Eddie Kaye Thomas as Adam Michael Cyril Creighton as Mel Lucas Kavner as Cecil Josh Grisetti as Ralph David Paymer as Harry Drake Peter Friedman as George Ben Rosenfield as 29-Year-Old Ethan Will Sasso as Carmine Streeto Sean Gunn as Stewart Jones Darren Criss as Taylor Danny Strong as Aaron Lebowitz Danny Garcia as Ray Ortiz Co Starring Malika Samuel as Dorie Steve Routman as Alan Yael Chanukov as Chava John Viener as Benny Clara Stack as Francesca Tuffy Questell as Dennis Adam Heller as Rabbi James Cribbins as Caddy Alanna Fox as Heather Eric Rizk as Morie Richard R. Henry as Cake Baker Jose Monge as Second Assistant Cook Elli Meyer as Cantor Christina Catechis as Linda Rory Scholl as Doubtful Guy Jesse Sharp as Len Blixton Genesis Oliver as Dougie Renata Friedman as Ruth Johnny Sanchez as Head Chef Sebastian Beacon as Record Executive Chris Cafero as Cameron Rob Cantrell as Doubtful Guy Don Noble as Sol Todd Faulkner as King Swing Pedro Morillo Jr. as First Assistant Cook R.J. Foster as Agent Scanlon Jason Babinsky as Tommy