Guest Stars Daniel K. Isaac as Ben Kim Dan Soder as Dudley Mafee Louis Cancelmi as Victor Mateo Stephen Kunken as Ari Spyros Allan Havey as Karl Allerd Will Roland as Winston Sarah Stiles as Bonnie Barella Zachary Unger as Kevin Rhoades Clancy Brown as Waylon 'Jock' Jeffcoat Jade Eshete as Lauren Turner Samantha Mathis as Sara Hammon Matt Servitto as Bob Sweeney Jack Gilpin as Sean Ayles Jerry O'Connell as Steven Birch Nina Arianda as Rebecca Cantu Tijuana Ricks as Tonelle "T" Burton Harry Lennix as Franklin Sacker Lily Gladstone as Roxanne Michael Rispoli as Richie Sansome Saul Rubinek as Hap Halloran Tanis Parenteau as Jane Halftown Sam Morril as Sam Co Starring Dhruv Maheshwari as Tuk Lal Zina Wilde as Helena Lilly Moran as Peach Alexa Jacqueline Swinton as Eva Rhoades Timothy Davis as Chef Ryan David Shih as Dr. Zhang Lei Marguerite Stimpson as Brienne Jim Chanos as Himself Scott Wapner as Himself Joshua M. Brown as Himself Deontay Wilder as Himself Christine Cartell as Dollar Bill's Wife #2 John G. Willink as Himself Jeff Yass as Himself Stipe Miocic as Himself Bob Menery as Himself Stacey Cunningham as Herself Matthew Baiamonte, Jr as Referee Bill Beydoun as Cop Tom Delgado as Husband Sherin Shetty as Coffee Runner Tim Ferriss as Himself (Timothy Ferriss) Meredith Travers as Wife Rich Eisen as Himself