Guest Stars Julie White as Maddie Biggs Alicia Sable as Tammy Stackhouse Brooke Bloom as Julie Carrell Kobi Libii as Aaron Stimson Ben Rameaka as James Whippy Natalie Gold as Katherine Sims Amy Sedaris as Louise Laffer Wanda Sykes as Senator Rosalyn DuPeche Haley Joel Osment as Shelby Mellman Willa Fitzgerald as Lola Laffer Richard Cox as Graydon Talbot Bjorn Dupaty as Hakeem Agabi Cynthia Nixon as Senator Carly Armiston William Thomas Evans as Senator Lamar Farkus Kenneth Tigar as Senator Paul Mower Ted King as Al Hickok Amy Hohn as Tess Sofiya Akilova as Marta Stjepanovi-Majdandzic Bill Murray as Senator Vernon Smits Marnie Schulenburg as Crystal Marylouise Burke as Betty Mower Owen Campbell as Dilly DeSantis Howard Fineman as Themselves Jonathan Alter as Himself Chris Matthews as Himself Frank Deal as Teddy Bungemack John Keating as Edward Grottlemeyer Ed Herbstman as Zeke Brubaker Matt Lauer as Himself Shae D'Lyn as April Mandela Steven Hauck as Dr. Albert Hydell Michelle Best as Constance Jakob Hawkins as Officer Joseph Kolinski as Clemont "Clem" Castles Erin Gann as Dylan Mayfair Evelyn McGee as Booker Jane Pauley as Herself