Molly Ringwald — Passed on Pretty Woman

Ringwald was offered the role of Vivian Ward in Pretty Woman before Julia Roberts. She turned it down. The film grossed $463 million worldwide and made Roberts the highest-paid actress in Hollywood, launching a career that has earned over $250 million. Ringwald was the biggest teen star of the 1980s (Sixteen Candles, The Breakfast Club, Pretty in Pink), but her transition to adult roles stalled precisely when this role could have redefined her. Roberts became America's Sweetheart. Ringwald became a cautionary tale about the difficulty of aging out of teen stardom.