Guest Stars Jonathan Lemire as Himself Andrew Ross Sorkin as Himself John Heilemann as Himself Eugene Robinson as Himself Claire McCaskill as Herself Chuck Rosenberg as Himself Adrienne Elrod as Herself Pablo Torre as Himself Dave Aronberg as Himself Ken Dilanian as Himself Michael Steele as Himself Mark Leibovich as Himself Dan Goldman as Himself Michael Tomasky as Himself Walter Isaacson as Himself Jon Cryer as Himself Molly Ringwald as Herself Emmitt Smith as Himself Jill Wine-Banks as Herself Robert Draper as Himself Kenneth Womack as Himself Jim Windolf as Himself