Guest Stars Aya Cash as Joan Simon Nate Corddry as Neil Simon Kelli Barrett as Liza Minnelli Rick Holmes as Fred Weaver Bianca Marroquín as Chita Rivera Christiane Seidel as Hannah Paul Reiser as Cy Feuer Evan Handler as Hal Prince Co Starring Chandler Head as Nicole Fosse Heather Lang as Sandy Justin Gazzillo as Young Bobby Anthony Rosenthal as Charlie Grass Tessa Grady as Wendy Stephen Plunkett as Paul Grantner Haylee Roderick as Kit Kat Girl Rachel Hilson as Jane Kaitlynn Edgar as Kit Kat Girl Victoria Ratermanis as Karin Alexa Poller as Gerde Georgina Pazcoguin as Fandango Girl Skye Mattox as Kit Kat Girl Ryan Fielding Garrett as Cabaret Pianist Claire Camp as Fandango Girl George Bamford as Robert Surtees Beth Dzuricky as Carrie Tarik Davis as Sweet Charity Assistant Director Andrew Kober as Tom Jim Schubin as Cabaret Production Assistant Fiona Horrigan as Costume Designer Ian Blackman as Roger Laura Osnes as Shirley MacLaine