Why Hollywood Lost Its Soul ft. Barry Diller | Shane Smith Has Questions
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October 23, 2025
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October 23, 2025
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1:04:46Now PlayingShane 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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Why Hollywood Lost Its Soul ft. Barry Diller | Shane Smith Has Questions
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