Sylvester Stallone landed the biggest ever deal of its type for a movie star in the mid-1990s: but the three picture plan would splutter after one.

Most star names who have long careers in Hollywood – and still manage to land good roles – generally go through some ebbs and flows. The trick is then to pick the right comeback movie, and then capitalise on it. Look at Bruce Willis: he was coming off the back of two notorious flops – The Bonfire Of The Vanities and Hudson Hawk – and he took a gamble on a couple of supporting role projects. The ones that didn’t do the trick were Mortal Thoughts and Billy Bathgate. The one that did was Pulp Fiction. It was a full-on career reboot.

In the case of Sylvester Stallone, he’s been through a couple. Firstly, in 1993, he starred in Cliffhanger and Demolition Man, released within half a year of each other and putting his ventures into comedy – Oscar, Stop! Or My Mom Will Shoot! – firmly behind him.

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Both his new action ventures were hits of varying sizes, most importantly international hits at that. And off the back of his newly-rediscovered box office cachet, he landed a run of enormous movie star deals. One of which was the biggest of its kind at the time.

Contextually, and rather helpfully for Stallone’s bank balance, this was in the era when the star paypacket was skyrocketing. The independent production company Carolco had stunned Hollywood after all when it agreed to pay Arnold Schwarzenegger a whopping $15m to star in Terminator 2: Judgment Day at the start of the 90s, paying off part of his fee with a plane.

Then, the goalposts shifted dramatically when Columbia broke the $20m up front salary barrier for an actor. It paid the funds to Jim Carrey, oddly for the dark and decidedly uncommercial The Cable Guy, which arrived in 1996. Bottom line: movie stars, even though they wouldn’t know it, were at the height of the era when they could demand big salaries and get them. Stallone’s agent got to work.

Firstly, Savoy Pictures was looking to make a mark, and the best way to get instant attention was to pay big bucks. At the time known for indies such as Shadowlands and Serial Mom, in 1994 it agreed to pay gigantic money for blockbuster projects. It forked out $2m for the rights to Tom Clancy’s Without Remorse, for instance, a film that’s only just been made with Michael B Jordan in the lead. And it offered Stallone $20m for an undisclosed project that at the time had neither a script or a title.

Perhaps unsurprisingly, Stallone said yes, although the project in question would never be realised. The company got out of the movie business a year after its Stallone deal, selling on its slate of projects.

No matter for Sly, as other buyers were keen for his services. In particular, Universal wanted him for the lead in its new disaster film Daylight (pictured). Whilst Nicolas Cage was reportedly considered for the movie, in the end the studio wanted someone with worldwide commercial appeal, and a cheque for $17.5m was duly written for Stallone.

This, then, was the peak of Stallone’s second coming, if you will. And boy, did he capitalise on it.

In August 1995, with Daylight a month away from the start of production, Universal tripled down on the Stallone business. Separate to his Daylight deal, Stallone agreed to star in three further films for the studio, at $20m apiece. What’s more, this was a non-exclusive deal, so he could still shop projects to other studios. All done in the aftermath of Carrey’s groundbreaking The Cable Guy deal (and crucially, before The Cable Guy was actually released).

Stallone though, notwithstanding the fact that Demolition Man’s grosses had fallen a little short of expectations, had earned himself the biggest non-exclusive deal ever inked between a studio and actor at the time. Universal was banking on the fact that Stallone’s second wave would be a prolonged one.

And yet, that’s not how it panned out. His box office successes were about to run out.

Firstly, there was the small matter of another film Stallone had made for Warner Bros, Assassins. Penned by the Wachowskis but dramatically changed from their script (to the point where they tried to take their name off the film), Sly was paid $15m for his work in that. Yet the film spluttered at the box office in 1995, as had him taking the title role of Judge Dredd earlier that summer. No matter: movie stars brought with them solid international box office, and that was the case with Stallone.

Daylight would follow in 1996 and was generally pretty well received, but again, the numbers his films were attracting were falling some way short of someone like Arnold Schwarzenegger. Furthermore, that same year Hollywood had been taught the latest lesson in the universal box office appeal of visual effects, when Independence Day cleaned up. Was the money best spent on computers over human beings?

By the end of 1997, without a picture in production as part of the deal, doubts were being raised about Universal’s wisdom with its Stallone package. That said, there were still projects being juggled.

One was Into Thin Air, that Lili Fini Zanuck was said to be directing. Following his low budget drama Cop Land – one of Stallone’s most acclaimed roles – this would have been a witness protection programme drama, but it never got made. Then there was a serial killer thriller called Suspect Zero, that Zak Penn had penned the script to.

In the end, the project Stallone opted for was D-Tox, a psychological thriller mixed with horror – perhaps influenced by Schwarzenegger taking on the horror-tinged End Of Days – for I Know What You Did Last Summer director Jim Gillespie. The film duly shot in the first half of 1999, for a $55m budget. Yet when the studio test screened an early cut at the end of that same year, it knew it had a problem. A huge problem. It got to the point where reshoots were going to be required, and production company Imagine Entertainment reportedly took its name off the project. The film ended up in limbo (Stallone made the remake of Get Carter straight afterwards, and that was released first). Eventually, after three years lingering on the shelf unreleased, Universal cut its losses.

But it already had with its cash-rich Stallone deal by the time the film finally made its debut. In 2000, with one movie it’d never release made, the deal was scrubbed. D-Tox – entitled Eye See You for its UK release – didn’t even make it to 100 screens in the US, and its total worldwide gross of $7m brought Stallone’s career revival to a shuddering stop.

Still, he’d get his second – arguably even more successful – career revival in the mid-noughties, when he elected to revisit two of his most popular roles. It’d be fair to say that his return to the world of Rocky Balboa was more critically popular than his choice to resurrect John Rambo (he’d get Oscar-nominated in the end for playing Rocky again in Creed. This time, he bore the risk, with the projects lower budget, and any upside to him based on profits and back-end. Plus, he gathered his old chums together for a new action film called The Expendables, which did rather well too.

Both those are stories for another time…

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