Guest Stars Joel Johnstone as Archie Cleary Bailey De Young as Imogene Cleary Brian Tarantina as Jackie Aaron Serotsky as Howard Fawn Nathan Thomas Williams as Washington Square Park Kid Steve Rosen as Marty Kahn Carolee Carmello as Loretta Co Starring Nunzio Pascale as Ethan Cynthia Darlow as Mrs. Moskowitz Holly Curran as Penny Pann Jack O'Connell as Jerry David Bluvband as Virgil Patrick O'Neill as Oz Alison Smith as Jane Jacobs Ambrose Martos as Ambrose / Comic Berry Basile as Mother Andrea Boehlke as Girl Singer Ashley Bryant as Janet Chaz Lamar Shepherd as Darius Jeffrey Litman as Acoustic Musician Allen Lewis Rickman as Red Skelton Daren Kelly as Elevator Operator Bobby Sanabria as Band Leader Timothy Basom as Acoustic Musician Dillon Kondor as Acoustic Musician Steven J. Cambria as Customer #1 Tony Manna as Table Guy Kate Wetherhead as Polly Sarah Bisman Storm as Customer #2 Harry Zittel as Lanie Michael X. Martin as Doorman Uncredited Scott Mena as Washington Park Bystander