Guest Stars Rae Dawn Chong as Betty Currie Judith Light as Susan Carpenter-McMillan George Salazar as George Conway Cobie Smulders as Ann Coulter Christopher McDonald as Bob Bennett Taran Killam as Steve Jones Danny Jacobs as Michael Isikoff Billy Eichner as Matt Drudge Elizabeth Reaser as Kathleen Willey Kim Matula as Laura Ingraham Co Starring Emma Malouff as Allison Tripp Jenny C. Paul as Susan Christopher Wallinger as Richard Porter Jim Rash as Ken Bacon Jamie Baer as Colleen James Thomas Gilbert as Jerome Marcus Jeff Elam as Gil Davis Emil Beheshti as Joe Cammarata Tim Redmond as Tim Russert Arthur Richardson as Magazine Stand Guy Theo Wilson as Newsweek Guy #2 Tamra Meskimen as Anne Farris Jung Park as Shopper Rebecca Bujko as Receptionist Dennis Atlas as Sales Associate Eli Revivo as Spa Stylist Grace Edwards as Teen