Guest Stars Jonathan Lemire as Himself Katty Kay as Herself Andrew Ross Sorkin as Himself John Heilemann as Himself Molly Jong-Fast as Herself Claire McCaskill as Herself Symone Sanders-Townsend as Herself Steve Kornacki as Himself David M. Drucker as Himself Jaime Harrison as Himself David Rothkopf as Himself Sherrod Brown as Himself Ben Mezrich as Himself Kaouther Ben Hania as Herself Angela Ferrell-Zabala as Herself Chris Willman as Himself