Sean Penn has spent much of his life going places most people only experience through headlines — wartime Kyiv with Zelenskyy, Chávez's Venezuela, Castro's Cuba, Iran before the Green Movement, and deep inside cartel country in Mexico with El Chapo. In this conversation with Shane Smith, Penn reflects on meeting Volodymyr Zelenskyy in wartime Kyiv, traveling through Iran before the Ahmadinejad era, spending time with Hugo Chávez and Fidel Castro, and the infamous journey that led to his meeting with El Chapo while the cartel leader was still on the run. Along the way, they talk about propaganda, journalism, war, political mythmaking, and why the story almost always changes when you go there yourself. Penn explains why he skipped the Oscars after winning his third Academy Award, what Americans misunderstand about Ukraine, why he was drawn to Chávez and Cuba, and what decades spent around power and conflict have taught him about human nature. This isn't a conversation about politics as much as it is about proximity — to history, to power, and to the people we are told to fear. Get 20% off your first order at ⁠https://www.mood.com⁠ with promo code SHANESMITH Save 20% on your first online Lucy order at ⁠https://www.lucy.co/ QUESTIONS⁠ with promo code QUESTIONS! #SeanPenn #ShaneSmith #Ukraine #Zelenskyy #Zelensky #ElChapo #Cuba #Chavez #FidelCastro #Venezuela #Iran #Journalism #Documentary #Politics #Propaganda #SSHQ #ShaneSmithHasQuestions #VICE #VICENews Subscribe to VICE News here: http://bit.ly/Subscribe-to-VICE-News Check out VICE News for more: http://vicenews.com Follow VICE News here: TikTok: https://www.tiktok.com/@vicenews?lang=en Facebook: https://www.facebook.com/vicenews Twitter: https://twitter.com/vicenews Instagram: http://instagram.com/vicenews =========================== Chapters: 00:00 Ukraine cold open 00:55 Sean Penn and Shane on Iran 15:10 Introduction 15:55 Hugo Chávez and Venezuela 23:31 Meeting Fidel Castro in Cuba 30:23 Why Sean Penn keeps going there 34:26 The full El Chapo story 1:05:32 L.A. County Jail and Richard Ramirez 1:14:06 Ukraine, Zelenskyy and Superpower 1:20:31 Russia, misinformation and America 1:27:54 People beyond propaganda 1:33:04 Closing ================================ Sean Penn on Zelenskyy, El Chapo and Seeing the World Up Close | Shane Smith Has Questions https://www.youtube.com/@VICENews