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- Hollywood Checkmate explores the difficulties of how young artists get their first break in the entertainment industry. Great qualifications, years of training, and a college degree may look good on a resume, but don't always equal a job. The Hollywood dream has become a nightmare for some. Can the next generation of creatives change the status quo and revoke the catch twenty-two that blocks them from starting a career? We'll meet with experienced veterans of the industry whose words of wisdom give solutions and inspire hope to the next generation.