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 Katrina Cunningham as Christina Fuego Diana Bologna as Fran Dwyer 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 Armand Assante as Mr. Martino Kelcy Griffin as Jennifer Preston E.J. Carroll as Fat Mooney James Ciccone as Carmine Patriccia Jimmy Palumbo as Robert DiBernardo Cate Bottiglione as Dr. Karen Wells Bryan Coffee as Sean Howard Olli Haaskivi as Dr. Oser Karen Giordano as TBD