Guest Stars Matilda Szydagis as Zelda Stephanie Hsu as Mei LeRoy McClain as Shy Baldwin Will Brill as Noah Weissman Justine Lupe as Astrid Weissman David Paymer as Harry Drake Sterling K. Brown as Reggie Daniel J. Watts as Henry Liza Weil as Carole Keen Wallace Shawn as Herb Smith Lenny Venito as Angie Calibresi Co Starring Matteo Pascale as Ethan Nunzio Pascale as Ethan Markita Prescott as Martha Steven Hauck as Dawes Reggie Talley as Billy Alysha Deslorieux as Dede Harvey Morris as Slim Brennyn Lark as Dawn Lino Del Core as Craps Dealer Kevin Isola as Stage Manager David Deblinger as Charlie Grayson Berry as State Journal Reporter Bella Muller as Cece Dana Stern as Anne Lyn Philistine as Roberta Reji Woods as Stu Rayna Starr as Mandy Tony Nation as Reno Gazette Reporter Matt Grossman as Lounge Sound Guy Brian Hatch as Bellboy Matt Hurley as Howard Jennifer Perry as Berta's Friend Brian Sills as Arnold Erik Gratton as Ted Garth Kravits as Eddie Major Warren Bub as Blackjack Player Brian Faherty as Dice Shooter