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Kevin O’Leary’s Shocking Hollywood Debut in Benny Safdie’s New Film

A casual afternoon on his dock led to an Oscar-worthy opportunity. How Kevin O’Leary’s bold move won over Hollywood’s elite—and critics.

The image shows a nurse shark swimming in the ocean near a coral reef. The shark is surrounded by a...
The image shows a nurse shark swimming in the ocean near a coral reef. The shark is surrounded by a variety of colorful fish and coral, creating a vibrant underwater scene.

Kevin O’Leary’s Shocking Hollywood Debut in Benny Safdie’s New Film

Businessman and TV personality Kevin O’Leary has revealed an unexpected turn in his career—an offer from director Benny Safdie to star in a Hollywood film. The proposal came while O’Leary was relaxing on his dock one summer afternoon. Safdie, known for Marty Supreme, reached out to O’Leary with a role in his upcoming project, featuring Timothée Chalamet and Gwyneth Paltrow. The part, originally intended for actor Abel Ferrara, was that of Milton Rockwell. Instead of traveling to meet the filmmakers, O’Leary insisted they fly to him from New York if the offer was genuine. His performance eventually earned high praise from critics and audiences alike. Sharing the screen with established stars, O’Leary’s acting debut stood out as a surprise success. The film marked O’Leary’s first major acting role, proving his ability to transition from business to entertainment. His involvement in the project added a unique twist to Safdie’s star-studded cast.

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