Guest Stars Daniel K. Isaac as Ben Kim Dan Soder as Dudley Mafee Louis Cancelmi as Victor Mateo Ben Shenkman as Ira Schirmer Glenn Fleshler as Orrin Bach Corey Stoll as Michael Prince Daniel Breaker as Roger 'Scooter' Dunbar Will Roland as Winston Eva Victor as Rian Rob Morrow as Adam DeGiulio Jade Eshete as Lauren Turner Matt Servitto as Bob Sweeney Roma Maffia as Mary Ann Gramm Rick Hoffman as Dr. Swerdlow Chelcie Ross as Robert "Hard Bob" Beaufort Caroline Day as Chelz Polly Draper as Senator Marcia Vandeveer Co Starring Dhruv Maheshwari as Tuk Lal Lilly Moran as Peach Alexa Jacqueline Swinton as Eva Rhoades Tom Colicchio as Himself