Guest Stars Rich Sommer as Lenny Elizabeth Perkins as Constance Papadopoulos Gillian Jacobs as Maggie Josh Stamberg as George Robert Curtis Brown as Marshall Chris Riggi as Dustin Beau Minniear as JJ Co Starring David Lee Hess as Phil Lincoln A. Castellanos as Daniel Samantha Shelton as Lounge Singer Robert Maffia as Furious Mobster Jeremy Shouldis as Gerald Scott Guilford Adams as Blaine Peters Michele Greco as Ugo Sami Cavestani as Beatrice