Guest Stars Jonathan Lemire as Himself Katty Kay as Herself Andrew Ross Sorkin as Himself Lisa Rubin as Herself John Heilemann as Himself Charlie Sykes as Himself Vaughn Hillyard as Himself Chris Matthews as Himself Pablo Torre as Himself Mark Leibovich as Himself Lauren Leader as Herself Jared Moskowitz as Himself Matt K. Lewis as Himself Daniela Pierre-Bravo as Herself Gretchen Whitmer as Herself Brian Klaas as Himself Kathryn Kolbert as Herself Julie F. Kay as Herself Simon Shuster as Himself