Guest Stars Sianoa Smit-McPhee as Annie Phoebe Neidhardt as Annie Douglas Smith as Young Man Maddie Corman as Phyllis Ivory Aquino as Cecilia Chung T.R. Knight as Chad Griffin Jayne Taini as Elouise Todd Weeks as Tom Ammiano Pauley Perrette as Robin William Sadler as Chuck Cooper Matthew Del Negro as Mayor Newsom Phylicia Rashad as Yvette Flunder Mary McCormack as Roberta Kaplan Henry Czerny as David Boies Rob Reiner as Mr. Blankenhorn Jack Plotnick as Gilbert Baker Richard Schiff as Judge Vaughn Walker Debra Winger as Justice Kagan Alexandra Grey as Seville Luis Jose Lopez as Victor Arliss Howard as Ted Olson Juan Riedinger as Jandro Jeremiah Birkett as Paul Sandy Steier as Themselves Larry Guli as Justice Scalia Alex Reznik as Mitch Larissa Laskin as Roma's Sister Jazzmun as Bobbi Jeff Zarillo as Himself Paul Katami as Himself Kris Perry as Himself Prado Yvel Gomez as Trans Singer Carla Pauli as Staffer