Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Al Sharpton as Himself Katty Kay as Herself Andrew Ross Sorkin as Himself John Heilemann as Himself Claire McCaskill as Herself James Stavridis as Himself Elise Jordan as Herself Vaughn Hillyard as Himself Chris Matthews as Himself Steve Kornacki as Himself Alexi McCammond as Herself Tim Kaine as Himself Tim Walz as Himself Uché Blackstock as Herself (Dr. Uché Blackstock)