In this episode of Monitoring the Situation, Marc Andreessen, Katherine Boyle, and Erik Torenberg dive into the movies that best explain America, from Once Upon a Time in Hollywood to Tropic Thunder to Fight Club. They explore how Tarantino’s revisionist masterpiece reimagines 1969 and the end of America’s cultural innocence, why Tropic Thunder was the last un-cancellable comedy, and how Fight Club evolved from a left-wing critique of capitalism to a right-wing prophecy about alienation and identity. Along the way, they trace the parallels between the counterculture of the 1960s and the internet culture wars of the 2010s, and debate whether we’re living through another great American cultural reset. 00:00 Intro 02:10 Los Angeles: The Ultimate “Fake It Till You Make It” Story 04:55 The 1960s Cultural Revolution 08:15 When the Dream Turns Dark: Manson and the End of the Sixties 10:40 Tarantino’s Twist on the Manson Murders 13:10 The Easter Eggs and Alternate History 16:00 Cliff Booth, Sharon Tate, and the Genius of the Ending 20:15 The Counterculture, Violence, and Comedy Collide 23:15 Why Audiences Laughed Through the Violence 26:30 What Tarantino Says About America 29:45 From Once Upon a Time to Tropic Thunder 33:10 Tropic Thunder: The Ultimate Hollywood Satire 36:30 Robert Downey Jr. in Blackface 40:50 Booty Sweat, Les Grossman, and the Genius of the Marketing 44:30 Satire, Offense, and How the Film Aged 48:20 Oppenheimer: Nolan’s Epic and Its Moral Dilemma 53:45 Was Oppenheimer the Hero or the Traitor? 01:03:00 The Morality of the Bomb and the Cold War Reality 01:08:40 AI, Scientists, and the Burden of Invention 01:12:30 Fight Club: Nihilism, Masculinity, and "Capital A" Art 01:15:30 Could Fight Club Be Made Today? 01:16:00 Closing Thoughts Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Thinking Big: https://www.goodreads.com/book/show/1161700.Thinking_Big Follow Marc on X: https://x.com/pmarca Follow Katherine on X: https://x.com/KTmBoyle Find a16z on X: https://x.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.