Guest Stars Daniel K. Isaac as Ben Kim Dan Soder as Dudley Mafee Louis Cancelmi as Victor Mateo Stephen Kunken as Ari Spyros Glenn Fleshler as Orrin Bach Allan Havey as Karl Allerd Corey Stoll as Michael Prince Daniel Breaker as Roger 'Scooter' Dunbar Will Roland as Winston Sarah Stiles as Bonnie Barella Keith Eric Chappelle as Everett Wright Rob Morrow as Adam DeGiulio Jade Eshete as Lauren Turner Samantha Mathis as Sara Hammon Matt Servitto as Bob Sweeney Roma Maffia as Mary Ann Gramm Mike Birbiglia as Oscar Langstraat Polly Draper as Senator Marcia Vandeveer Cindy Cheung as Ali Kashkhokh Darren Goldstein as Simon Shenk Mark Blum as Dr. Mark Rutenberg Co Starring Dhruv Maheshwari as Tuk Lal Zina Wilde as Helena Kira Visser as Donna Lilly Moran as Peach Henri Binje as Bram Longriver Bregje Heinen as Model Grace Su as Realtor Alok Tewari as Jules Hakli Missy Robbins as Herself Lou Lentino-Rodriguez as MC Hikaru Nakamura as Himself Ivy Askew as Herself Sean Feeney as Himself Kelsey Lea Jones as Brandi / Dancer