Guest Stars Joel Johnstone as Archie Cleary Bailey De Young as Imogene Cleary Reid Scott as Gordon Ford Alfie Fuller as Dinah Rutledge Will Brill as Noah Weissman Justine Lupe as Astrid Weissman John Scurti as Nicky Gideon Glick as Alfie Erik Palladino as Frank Kayli Carter as Gloria Dominic Jay Will as James Jackie Hoffman as Gitta Marceline Hugot as Molly Milo Ventimiglia as Sylvio Sarah Stiles as Angry Wife Co Starring Matteo Pascale as Ethan Clark Gayton as Wolford Band Member Andy Stein as Wolford Band Member Jon Kellso as Wolford Band Member Kirsten Wyatt as Mitzi Allison Guinn as Bunny Gregory Jones as Wolford Band Member Stewart Cutler as Wolford Band Member Aaron Heick as Wolford Band Member Rich Pagano as Wolford Band Member Jillian Schmitz as Philomena Raven Bowens as Tilly Paulina Yeung as Jukebox Vocalist Aaliyah Butler as Cissy Kyle Keyes as Thomas Shedrick Mitchell as Wolford Band Member Zurin Villanueva as Lill Nancy Nagrant as Julie Kenton Chen as Jukebox Vocalist Loriel Hennington as Dorothy Abigail Donaghy as Sixteen-Year-Old Midge Deborah Guyer Greene as Luncheon Woman Rebecca Knowles as Luncheon Woman Ivory Fox as The Wicked Witch Armand Anthony as Alden Christa Scott-Reed as Spa Voiced Lady Autumn Withers as Ethel Kennedy Daniel Harray as Priest Hilary Maiberger as Jackie Kennedy Amy Greenspan as Luncheon Woman Jeremy Carlisle Parker as Luncheon Woman
