In 1996, actor Michael Caine confidently bet a pound that Alan Parker's musical Evita, starring Madonna, would spark a worldwide fashion trend, with women everywhere copying its 1940s-inspired hairstyles and dress. Caine's prediction, made shortly before the film's December 1996 release, reflected his belief that Madonna's performance and styling would leave a lasting cultural mark, though he had no notable track record himself of appearing in genuinely trend-setting films.

The prediction proved wrong: Evita neither triggered a mass fashion revival nor became a major box-office phenomenon, though it did win the Oscar for Best Original Song and earned Madonna a Golden Globe for Best Actress in a Comedy or Musical. Caine made the bet around the same period Jack Nicholson persuaded him to abandon retirement and star in Blood and Wine, reigniting his acting career. Ultimately, his wager cost him little, as he had only staked a single pound on the outcome.