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 Amy Sedaris as Louise Laffer Natalie Gold as Katherine Sims Haley Joel Osment as Shelby Mellman Wanda Sykes as Senator Rosalyn DuPeche 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 Sofiya Akilova as Marta Stjepanovi-Majdandzic Amy Hohn as Tess Marylouise Burke as Betty Mower Marnie Schulenburg as Crystal Bill Murray as Senator Vernon Smits Jonathan Alter as Himself Owen Campbell as Dilly DeSantis Chris Matthews as Himself Howard Fineman as Themselves 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