Guest Stars Mustafa Shakir as Big Mike Andrea-Rachel Parker as Bernice Thaddeus Street as Black Frankie Genevieve Hudson-Price as Jocelyn Diana Bologna as Fran Dwyer Michael Gandolfini as Joey Dwyer Zoe Kazan as Andrea Martino Ryan Farrell as Greg Taylor Larisa Polonsky as Shana Calvin Leon Smith as Reggie 'Reg' Winhorn Paloma Guzmán as Pilar