Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Lisa Rubin as Herself John Heilemann as Himself Jennifer Palmieri as Herself Molly Jong-Fast as Herself Claire McCaskill as Herself Chris Matthews as Himself Barbara McQuade as Herself Chris Christie as Himself David M. Drucker as Himself Christopher Krebs as Himself James Clyburn as Himself Carlos Curbelo as Himself Erik Larson as Himself Keegan-Michael Key as Himself Jake Sherman as Himself David Jolly as Himself Brendan Buck as Himself Andrea Bernstein as Herself