Guest Stars David Jolly as Himself Harry Litman as Himself Molly Jong-Fast as Herself Basil Smikle as Himself Eddie Glaude as Himself Mini Timmaraju as Herself Marc Elias as Himself Paul Rieckhoff as Himself John Heilemann as Himself Ben Rhodes as Himself Greg Bluestein as Himself Nick Corasaniti as Himself Fiona Hill as Herself Ashley Parker as Herself