In the summer of 2003, Disney executives were extremely nervous about the film that had been earmarked as that season’s big picture: Pirates of the Caribbean. Part of the reason for their fear was that its star Johnny Depp was apparently giving an unhinged and quixotic performance in the lead role, but the greater concern was the appalling financial track record of swashbuckling films about buccaneers.

Many of those that had been made over the previous decades – Steven Spielberg’s Hook; Roman Polanski’s Pirates; even the Graham Chapman vehicle Yellowbeard – had been significant critical and commercial disappointments. But none came close to the infamy of Renny Harlin’s 1995 picture Cutthroat Island. It became the biggest flop in the history of cinema, bankrupting its production company in the process and destroying the careers of its director and stars.

In the end, Pirates of the Caribbean was an enormous hit, in large part because of Depp’s unique interpretation of Captain Jack Sparrow, and it resurrected the genre. This was entirely what Carolco Pictures had been hoping for when they decided to make Cutthroat Island, a pirate adventure film starring Michael Douglas and Geena Davis, in 1993. Carolco had enjoyed significant success in the Eighties and Nineties with such male-focused films as Basic Instinct (with Douglas) and Terminator 2: Judgement Day, but it had also lost a vast amount of money due to ill-conceived foreign sales and a naïve belief in the power of paying movie stars huge amounts to sell their films. Get the big names, the logic ran, and audiences will come in droves.

To a point, this had succeeded, but the casting of Michael Douglas in Cutthroat Island as the con artist protagonist William Shaw – as much comic relief as heroic lead – seemed an odd choice, and the decision to pay him an astronomical $13 million was bold, to put it mildly. The powerful Douglas rewrote the script to his own specifications, and seemed happy with the result, saying "I was looking for a romp, for a sort of positive change away from the dark films I'd been doing." Renny Harlin, an action specialist who had had big hits with Die Hard 2 and Cliffhanger, was signed up to direct, and he brought in his new wife Geena Davis as the female lead, the pirate Morgan Adams.

Pre-production initially went smoothly enough, but problems soon arose. The first was that Douglas believed that the script was being weighted against his character in favour of Davis’s. As he later said, "I just was not comfortable with the part. The combination of not seeing it on the page and not knowing where it would go. I was feeling uncomfortable, and I wanted out." He also felt that the relationship between Harlin and Davis would make compromise difficult.

"I said 'Renny, you're married to the leading lady. Don't you think you have to do something to make me comfortable with this?' He agreed. There had to be something there." Eventually, Harlin said he would not alter the script, and Douglas replied: "God bless you. I'm not." In July 1994, shortly before filming was due to begin in Malta, the actor pulled out. It would be the wisest career decision he ever made.

Under normal circumstances, filming would have been delayed indefinitely until an actor of equal calibre had been recruited, but Carolco was in the unfortunate position that it was only surviving as a company due to the foreign sales that it had pre-sold with Cutthroat Island to the tune of $50 million. In a situation that bore unfortunate parallels to the central scam in Mel Brooks’ The Producers, Carolco had to make the film, whatever its quality, or face immediate bankruptcy.

After cancelling its other planned blockbuster, the Arnold Schwarzenegger vehicle Crusade that was to have been directed by Paul Verhoeven and losing millions in the process, Carolco had no other option but to proceed with the picture. Neither Harlin nor Davis had any interest in making the film since Douglas’s departure, with Harlin later commenting: "We begged to be let go. We begged that we didn’t have to make this movie. We begged that we not be put in this position. Geena was scared mindless about headlining this film. We felt that a pirate movie with a female lead was suicidal, but we were contractually obligated."

Davis said shortly after its release, "I, of course, assumed the whole project would be cancelled. It was all based on Michael Douglas being in it. To my horror, I learned not only would they not cancel but that I had a legal obligation to go ahead, unlike Michael. I tried desperately to get out of this movie. The ludicrous thing was that the only reason I was there was because of Michael. I never wanted to carry this movie."

The script was rewritten once again, this time to make Davis's character Morgan the hard-bitten but heroic protagonist, and then pre-production recommenced in Malta at vast expense without a lead actor. Virtually every male actor of appropriate age was approached to play Shaw, from the understandable (Keanu Reeves, Mel Gibson) to the bewildering (Jeff Bridges, Tim Robbins). Everyone turned it down.

And then, finally, Matthew Modine, at that point best known for his appearance in Kubrick’s Full Metal Jacket, was cast. He was considerably cheaper than Douglas, but even Modine would have conceded that he did not have the star power to bring an audience to a film like this, putting even more pressure on Davis and Harlin.

When production began, Harlin told his crew that "I want to see the most spectacular and eye-popping sets, the most interesting and unusual props, and especially weapons and special effects that leave the audience gasping in awe and stunts that no one thought possible before". Instead, however, virtually everything that could go wrong went wrong.

The producer David Nichols quit, the cinematographer broke his leg, which led to his departure, and Davis repeatedly injured herself while performing her own stunts. At one stage, the actors found themselves swimming in a water tank into which raw sewage had leaked: a fitting metaphor for the creative process. Most of them then fell ill from food poisoning.

Some light relief, at least, came with the casting of Oliver Reed as the notorious pirate Mordechai Fingers. He appeared in Malta the day before filming, and celebrated his arrival by becoming rip-roaringly drunk in a Maltese bar in front of the cast and crew, including Davis and Harlin. As the evening progressed, Reed exposed his penis to show off an eagle tattoo, to Davis's great horror.

The next morning, Reed received a letter from the production company informing him he had been fired "for inappropriate behaviour related to alcohol". (Clearly, Malta did not agree with Reed. When he returned a few years later to film a role in Gladiator, he died following a drinking binge in which he challenged sailors a third of his age to an arm wrestle.)

The production for Cutthroat then moved from Malta to Thailand, at extortionate expense. The ships each cost $1m to build: full-sized replicas of 17th-century sailing vessels with 20 cannons on each side. Horses were flown in from Austria. By the time it wrapped on April Fool’s Day 1995, the total cost was $100 million, which meant that it would need to make around $250 million to return any kind of profit.

But the rushed production and hacked-about script had taken their toll, and the final film was released with minimal publicity and to dreadful reviews. The New York Times called it "too stupidly smutty for children and too cartoonish for sane adults". The Washington Post went harder: "It takes a two-hour act of will to keep facing the screen during this moribund movie."

Modine, a sensitive soul who had predominantly played roles in arthouse pictures, was especially horrified by its reception. He remembered that, after the premiere, "The papers were all outside my door. And I thought, ‘Well, I’ll read one of ‘em.’ And it was horrible! And then I thought, 'There’s got to be one that’s good.' And it was just one after the other that was horrible, horrible, horrible. And I went downstairs to have breakfast and I felt like everybody in the café was looking at me going like, ‘Oh my God! The walking dead,’ you know."

He even went on to confess that "I went up to my room, and I’m not going to lie. I didn’t want to kill myself, but I wanted to hang myself in the bathroom so that when the cleaning lady came in to do the room, that she’d find me and say, ‘Oh my God!’ and call. Because I wanted people to know how much that hurt — that I did the very best that I could on the film, as did everybody that was working on the film."

It was a massive financial disaster, losing around $100 million, and finishing off Carolco in the process. The film was pulled from US cinemas after two weeks with just $10m of sales. It may still be the biggest box office failure in Hollywood history, and reputations were damaged beyond repair. Davis and Harlin’s next collaboration, the far superior Long Kiss Goodnight, was also a financial failure, and it is perhaps unsurprising that the couple eventually divorced in 1998. Modine, while acknowledging that Cutthroat Island did his career no favours, loyally defended it, saying years later that ‘it’s actually a really fun pirate movie, [and] Renny Harlin did a good job.’ Does he have a point?

Watched again, 25 years after it originally came out, there are undeniably things to enjoy about Cutthroat Island, despite its 40 per cent Rotten Tomatoes rating. Frank Langella is marvellously camp and OTT as the film’s villain, Dawg Brown, and it is one of the last grand examples of pre-CGI filmmaking. Harlin’s desire that the money should be visible on screen was largely fulfilled, even if some of the action scenes do not so much strain credibility as destroy it entirely.

Why, for instance, in an elaborate carriage chase scene involving Davis and Modine’s characters, should a naval frigate be firing at the carriage, destroying half the town in the process? And John Debney’s stirring score has been a mainstay of trailer music ever since, giving the film at least some afterlife.

But the central problem is that the chaotic production caused flaws on virtually every level. The storyline makes next to no sense, and is not helped by its terrible script (co-written by Marc Norman, who would later win an Oscar for co-writing Shakespeare in Love) and wooden performances. Davis looks frightened most of the time, which is understandable, given the behind-the-scenes circumstances, but something of a drawback when playing a ruthless pirate.

Meanwhile Modine seems bemused at the sheer inanity of most of his dialogue. It is also alternately frenetic and dull, inspiring alternate yawns and sniggers. By the time Davis dispatches Langella with the line "Bad Dawg!’" it is all one can do not to wish that the audience can be put out of its misery, too.

All the same, for all of its innumerable faults, Cutthroat Island is well worth watching, both for its many moments of unintentional hilarity and as a cautionary tale of Hollywood excess. Harlin put it best when he said, much later, "It was a good reminder that when you start believing in yourself too much, and thinking that you’re a genius, that someone brings you down and says, like, 'OK, you’re definitely not a genius, and you’ve had a good run, but you have to be humble and play by the rules.’ We did the best we could under the circumstances. So, was it painful when it all came crashing down? Yes. Did we learn a lot? Yes.’ He has now received five Golden Raspberry Award nominations for Worst Director – Cutthroat Island being his second – but continues to work prolifically.

As for Davis, she managed an impressive second act in her career, winning a Golden Globe for her role as America’s first female President in television drama Commander in Chief in 2006, and the honorary Jean Hersholt Humanitarian Award at the Oscars in 2019. And, when reflecting on what happened many years later, she remained philosophical. "I mean, I got to play a pirate captain! I got to do every type of role, even if the movie failed."

If only she had slurred her speech, worn heavy eyeliner and hinted at strange sexual peccadilloes a la Captain Jack Sparrow, the role, and the film, could have been an extraordinary success, after all.