S5 EP2: Sean Penn on dining with Jack Nicholson and Putin, run-ins with the paparazzi, and his relationship with Zelenskyy

41 snips

May 13, 2025

In a candid conversation, Sean Penn, an Oscar-winning actor known for his powerful roles in films like Milk, shares tales from his vibrant life. He recounts dining with legends like Jack Nicholson and Vladimir Putin, and discusses his relationship with Ukrainian president Volodymyr Zelenskyy. The challenges of dealing with paparazzi and the emotional toll of fame also feature prominently. Penn reflects on the intersection of Hollywood and politics, raising profound questions about truth, identity, and the complexities of celebrity culture.

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INSIGHT

Trump’s Perception of Truth

Sean Penn believes Trump truly thinks what he says, even if it is a lie.
Trump doesn't distinguish between truth and falsehood, focusing solely on what benefits him.

INSIGHT

Hollywood’s Avoidance of Ukraine Films

Films about Ukraine’s war often lack distribution due to financial interests in Russia.
Hollywood prioritizes money over timely, important stories, revealing its pervasive cowardice.

INSIGHT

Zelensky’s Rise and Stance

Zelensky rose to popularity as a comedian and actor before becoming Ukraine's president.
His moderate stance suggested peace with Russia, contrasting prior leaders' hawkish views.

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