Molly Ringwald — Passed on Pretty Woman

Molly Ringwald turned down the lead role of Vivian Ward in “Pretty Woman,” which grossed $463 million worldwide and catapulted Julia Roberts to become the highest-paid actress, earning over $250 million. Ringwald, a 1980s teen icon from “The Breakfast Club” and “Pretty in Pink,” saw her adult film career stall without this pivot. Unlike #4’s missed role, her decision cost her a $250 million franchise and a benchmark transition: Roberts reigned as America’s Sweetheart, while Ringwald’s star dimmed, illustrating the challenge of shedding teen fame.