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Sat 22 August 2026 18:15, UK
Movies have the potential to change the world in many different ways, and Michael Caine was so confident that one of them would join the club that he bet one whole British pound on it.
It wasn’t the riskiest wager he could ever place, but he nonetheless put his money where his mouth was, even if it wasn’t very much money, and his mouth turned out to be wrong when the film’s impact on the cultural consciousness and the planet at large was negligible at best.
The two-time Academy Award winner starred in many great pictures during his legendary career, and more than a couple of masterpieces, but he was never in anything that could genuinely be called a game-changer or an industry-shaker, never mind any flick that turned the culture upside down.
With that in mind, maybe he wasn’t in the most knowledgeable position to comment, and his association with cinema was tenuous at the time, seeing as 1996 was the year that Jack Nicholson convinced him not to permanently retire from acting to make Blood and Wine instead, which reinvigorated Caine’s creative juices.
As mentioned, movies have the power to move figurative mountains, whether it’s instigating real-world change, shining a mainstream spotlight on timely issues, spawning a thousand imitators, or, in the case of titles like Rebel Without a Cause, Clueless, The Matrix, and Breakfast at Tiffany’s, made the look of their characters an aspirational goal, inspiring far too many people to start copying their ensemble.
The latter might not be the most important way for a movie to leave a lasting imprint on culture and society, and speaking of folks who’ve left a lasting imprint on culture and society, Madonna fits neatly into that camp, and Caine was convinced that the best performance of an otherwise horrendous acting career was destined to kill two birds with one stone.
“I’ll bet you a pound right now,” the veteran declared, shortly before Alan Parker’s Evita was released in December ’96. “I’ll bet you a pound that within weeks of that film coming out, every girl will be walking around with an Evita hairdo and dress. Bet you a pound, right now! And it’s going to be the whole Evita thing, with the funny shoes from the ’40s and the whole look.”
Further reading: Cutting Room Floor
Caine was so confident that he even doubled down. “Madonna was in that costume for months before they even started the movie, and all the girls are picking up on it,” he insisted. “So there you are. Pound. Right now!” He saw a sea change coming, but did Evita become such a juggernaut that it really did change the world, as the Italian Job star had prophesised? In short, did it fuck.
It wasn’t a great movie, and it wasn’t a massive hit, but it did claim the Oscar for ‘Best Original Song’ and win Madge a Golden Globe for ‘Best Actress – Comedy or Musical’. In terms of the footprint it left on the world beyond its run in theatres, it was virtually non-existent, but at least he didn’t bet more than a quid on it.
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