Guest Stars Daniel K. Isaac as Ben Kim Dan Soder as Dudley Mafee Dhruv Maheshwari as Tuk Lal Louis Cancelmi as Victor Mateo Ben Shenkman as Ira Schirmer Allan Havey as Karl Allerd Terry Kinney as Hall Will Roland as Winston Eva Victor as Rian Toney Goins as Philip Charyn Rob Morrow as Adam DeGiulio Piper Perabo as Andy Salter Harry Lennix as Franklin Sacker Rick Hoffman as Dr. Swerdlow Matthew Lillard as Ron Chestnut Co Starring Kira Visser as Donna Lilly Moran as Peach Susan Blackwell as Kristy Sandra Elizabeth Rodriguez as Older Lawyer Omar Ghonim as Another Lawyer Davide Borella as Artist Dipa Anitia as Teacher Questlove as Himself Mia Caress as Anne Linden Tailor as Busboy Michelle Sohn as Claire Colleen Clinton as Diana Samantha Sherman as Naomi Dara Adler as Linda