Shane Smith sits down with Hollywood titan Barry Diller, the media mogul behind Paramount Pictures, 20th Century Fox, QVC, Expedia, and IAC, for a sweeping journey through one of the most remarkable careers in modern entertainment. From his mailroom days at William Morris to creating the “Movie of the Week” at ABC, Diller recounts how failure, luck, and relentless curiosity shaped his path to becoming one of the most powerful figures in media. He opens up about his nervous breakdown at 19, the creative chaos of running Paramount during Grease, Raiders of the Lost Ark, and Beverly Hills Cop, and how he embraced technology early, spotting the potential of interactivity decades before the internet boom. Shane and Barry dive into the lost art of creative confrontation, the decline of instinct in Hollywood, and the tectonic shift from storytelling to data-driven content. Diller also shares deeply personal reflections on his relationship with Diane von Furstenberg, his sexuality, and how a lifetime of contradictions, the shy kid who became a global powerbroker, has defined him. Along the way, there are stories of Beverly Hills scandals, the Munich Olympics tragedy, near misses with Amazon stock worth billions, and why Barry still believes his greatest bet was always on curiosity itself.

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