Guest Stars Mustafa Shakir as Big Mike Andrea-Rachel Parker as Bernice Kim Director as Shay Ralph Macchio as Officer Haddix Thaddeus Street as Black Frankie Anwan Glover as Leon Aaron Dean Eisenberg as Todd Lang Alysia Reiner as Kiki Rains Diana Bologna as Fran Dwyer Katrina Cunningham as Christina Fuego Michael Gandolfini as Joey Dwyer Corey Stoll as Hank Jaffe Zoe Kazan as Andrea Martino Ryan Farrell as Greg Taylor Calvin Leon Smith as Reggie 'Reg' Winhorn Kelcy Griffin as Jennifer Preston Armand Assante as Mr. Martino E.J. Carroll as Fat Mooney James Ciccone as Carmine Patriccia Jimmy Palumbo as Robert DiBernardo Olli Haaskivi as Dr. Oser Cate Bottiglione as Dr. Karen Wells Bryan Coffee as Sean Howard Karen Giordano as TBD