The disastrous movie Oliver Stone called “the biggest challenge of my life”

Passion projects can often be a double-edged sword, something Oliver Stone found out the hard way when a story he’d spent decades developing and poured every ounce of himself into turned out to be nothing but an unmitigated disaster.

Of course, in many cases, a filmmaker spending decades working on a single film can reap huge rewards and completely justify their decision to dedicate so much of themselves to the story, as Martin Scorsese’s Gangs of New York and Christopher Nolan’s Inception proved beyond any doubt.

However, there’s a thin line between a passion project and a vanity project, something Michael Cimino’s Heaven’s Gate and Kevin Costner’s The Postman found out to their massive detriment. With four Academy Award wins and a string of classics to his name, though, Stone was already firmly established as one of his generation’s foremost auteurs.

Thanks largely to the success of Gladiator, the historical epic was big business for the first time in a long time, which, on paper, presented Stone with the ideal opportunity to mount his blockbuster retelling of Alexander the Great’s rise and fall. One issue was that Baz Luhrmann was developing a very similar film at the exact same time, but the Platoon director stuck to his guns and eventually won that particular race.

Describing it as “the biggest challenge of my life” in an interview with the BBC, Stone admitted that his number one hope was that he “can do it some justice”. Explaining why it had taken him so long to get around to the movie, he said it was all about the story: “My race was always with the script. It was ‘how do you make a story’, because it’s a great story, but if you go for surface events it will never work.”

In a prophetic moment, Stone acknowledged not only how “it’s very hard to do,” but even though he wasn’t sure whether he had or not, he was “about to take the shot” anyway. Unfortunately, he missed his shot by miles, with Alexander going down as a catastrophic box office bomb that was torn limb-from-limb by critics.

Star Colin Farrell was so confident Stone had cranked out yet another masterpiece that he was dreaming of awards season glory, and while that was technically the case, six nominations at the Golden Raspberry Awards, including ‘Worst Picture’, ‘Worst Director’, and ‘Worst Actor’ wasn’t what anybody had in mind.

Adding insult to injury, Alexander bombed spectacularly at the box office, and not even an additional three cuts released by Stone could hammer it into serviceable shape. He may have called it the biggest challenge of his career, but it was hardly one that he proved himself up to in the long run.

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