Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Andrew Ross Sorkin as Himself John Heilemann as Himself Eugene Robinson as Himself Sam Stein as Himself Vaughn Hillyard as Himself Chris Matthews as Himself Ali Vitali as Herself Raf Sanchez as Himself Jen Psaki as Herself Sahil Kapur as Himself Mychael Schnell as Herself Michael Tomasky as Himself Sarah Longwell as Herself Maggie Hassan as Herself