Shane Smith Has Questions

Go There. With Sean Penn (2026x17)

Air date: Jul 16, 2026

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.