Guest Stars Rae Dawn Chong as Betty Currie Judith Light as Susan Carpenter-McMillan George Salazar as George Conway Christopher McDonald as Bob Bennett Cobie Smulders as Ann Coulter 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 James Thomas Gilbert as Jerome Marcus Jamie Baer as Colleen Emil Beheshti as Joe Cammarata Jeff Elam as Gil Davis Tim Redmond as Tim Russert Theo Wilson as Newsweek Guy #2 Arthur Richardson as Magazine Stand Guy Tamra Meskimen as Anne Farris Jung Park as Shopper Dennis Atlas as Sales Associate Rebecca Bujko as Receptionist Eli Revivo as Spa Stylist Grace Edwards as Teen