Guest Stars Hillary Clinton as Herself Julia Louis-Dreyfus as Herself (Moderator) Lawrence O'Donnell as Himself Cory Booker as Himself (Sen. Cory Booker) Claire McCaskill as Herself Michael Steele as Himself Jon Meacham as Himself James Carville as Himself Steve Schmidt as Himself Jill Biden as Herself Julián Castro as Himself Charlie Sykes as Himself Tammy Baldwin as Herself (Sen. Tammy Baldwin) Ayanna Pressley as Herself (Rep. Ayanna Pressley) Karine Jean-Pierre as Herself