Guest Stars Sonny Valicenti as Matt Cohler Darren Pettie as Hendricks Ian Alda as Peter Fenton Mousa Kraish as Fawzi Kamel Noah Weisberg as Quentin Joel Kelley Dauten as Ryan Graves Annie Chang as Angie You Rama Vallury as Tahir Khan Damon Gupton as David Drummond Chelcie Ross as David Bonderman Erinn Ruth as Olivia Lungociu Virginia Kull as Jill Hazelbaker Amanda Brooks as Rachel Whetstone Brian Howe as Donald Kalanick Jessica Hecht as Amy Gurley Mishka Thébaud as Cory Kalanick Jeremy Howard as Anthony Levandowski Mark Gessner as Gil Hill Harper as Eric Holder Nick Fondulis as Dan O'Sullivan Co Starring Quentin Tarantino voices Himself (Tarantino's Voice) Alex Skinner as Matt Joy Corrigan as Woman 1 Anna MacDonald as Woman 2 Adam Foster Ballard as Roommate London Kim as Uber Employee #2 Lisa Roumain as Sonya Steve Holm as Uber Employee #1 Jonte as Uber Tech #1 Al Bayan as Uber Tech #2 Brandon Hudson as Uber Employee #3 Will Green as Hugh