Guest Stars Julie White as Maddie Biggs Alicia Sable as Tammy Stackhouse Brooke Bloom as Julie Carrell Ben Rameaka as James Whippy Kobi Libii as Aaron Stimson Natalie Gold as Katherine Sims Amy Sedaris as Louise Laffer Willa Fitzgerald as Lola Laffer Richard Cox as Graydon Talbot Cynthia Nixon as Senator Carly Armiston Kenneth Tigar as Senator Paul Mower Owen Campbell as Dilly DeSantis Jonathan Fried as Counsel Howard Fineman as Themselves Jonathan Alter as Himself Joseph Dellger as Senator Popper Chris Matthews as Himself Christine Lin as Reporter #3 Cadden Jones as Reporter #5 Eric Stafford as Reporter #1 Charles Schumer as Himself Regina Schneider as Reporter #2 Mellini Kantayya as The Nurse Michael Dean Morgan as Reporter #4 Andy Powers as Matthias