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. Subscribe to VICE News here: http://bit.ly/Subscribe-to-VICE-News Book your doctor's appointment at https://www.zocdoc.com/shane Get 50% off your first box, plus free breakfast for 1 year at https://www.factormeals.com/SHANE50OFF and use code SHANE50OFF #VICENews #news #sshq 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 More videos from the VICE network: https://www.fb.com/vicevideo ============================= Chapters 00:00 Welcome, Barry Diller! 05:20 Behind the Beverly Hills Image 11:02 OCD, Breakdown, and Anxiety 15:07 Barry's Side of the Story 19:53 Self-Reflection in Success 25:07 Confrontation the Key to Success 31:37 Embracing Technology into Art 33:25 The Best Ideas Started with a "No" 38:30 Introducing the Internet to the Business 42:30 Expidia and September 11th 45:35 The Exposure of Public Speaking 47:12 The Idea of Living in a Good Hotel 49:46 Barry and the Munich Olympics 52:30 Building Character 55:21 The Love Story Between Dion and Barry 1:00:12 The Reason Behind the Separation ============================= Why Hollywood Lost Its Soul ft. Barry Diller | Shane Smith Has Questions https://youtu.be/0pMQvKMw_cA