It took a long time for Sean Connery to agree to make a second Highlander film – and even then, his appearance came with a few challenges.

In the book that lists all of the great movie sequels, you’d need a bloody good pair of glasses to find a reference to Highlander II: The Quickening. A film so messed around by financiers that its director walked out of its premiere, whose reviews were hostile to the point of declaring it one of the worst movies ever made. Even whose fans admit that it’s, well, ‘troubled’.

One or two alternate cuts have since tried to repair some of the damage of the 1991 film, but for a much-anticipated sequel, Highlander II remains a tough film to love.

It was also a brutally difficult film to make. At some point we’ll come to it in a podcast episode, but it’s worth zeroing in on the challenges both of luring Sean Connery – arguably the original film’s highest profile star – back for the sequel, and then the further pressures when he arrived on set.

The original film had featured 18 minutes of Connery in the role of the immortal Ramirez, and it was something of a coup to get him involved (appreciating his latest career revival at that stage was still a couple of years off). Christopher Lambert took the lead, and upon release in 1986, the Russell Mulcahy feature seemed to struggle. A $19m production budget returned $12.9m at the box office. There was little appetite for a sequel.

But then word of mouth spread, and the movie became a sizeable video hit. To the point where a sequel not only was coming together, but a handsome budget of over $30m was to be spent on it (although the original plan was around $22m).

Christopher Lambert and Russell Mulcahy both agreed to return as star and director, but to raise the money and to keep the film’s global appeal, the backers knew that Sean Connery was needed too. An offer went out to him, but he hardly bit their hand off.

After a year of script revision work, and a lot of toing and froing over the screenplay, Connery would – as Film Review magazine reported back in October 1990 – sign his contract after 30 weeks of will he/won’t he. He’d been unhappy for some time about the lack of humour in early drafts, and it took a lot of work to get him to a point where he would commit. But commit he eventually did.

Some of the crew were a bit nervous too. Connery by reputation was never one to suffer fools gladly, and the fact that the movie was having to shoot far away in Argentina wasn’t going to help. It wasn’t Mulcahy’s first choice of location, and it caused the production no end of problems too when the exchange rate of local currencies fluctuated wildly against the American dollar during production.

“It got to the point where banks closed for five days, and no retailer would sell us vital raw materials because the price could double tomorrow, production designer Roger Hall said at the time.

With Connery then, in the end he inked a contract worth $3m in exchange for just two weeks of filming time. That was their lot. Mulcahy assembled a core crew of British and American technicians for the Argentinian shoot (who would have an idea what to expect from the star), but also knew that Connery would only work 12 hours a day under the regulations imposed by local filmmaking authorities.

To maximise his time, a helicopter was therefore hire at extra expense to cut out the two hour drive he’d otherwise have to do every day to the location. Because all concerned knew too that they needed to get at least 20 minutes of Connery into the final cut of the film for that $3m price tag. Some feat that was going to be too, with just two weeks of filming time on a complex science fiction film to land the necessary footage of him.

But it was a target that absolutely had to be hit, for this was a condition of the pre-selling to overseas distributors, that had raised the budget for the film in the first place. Connery’s name, bluntly, had been used to get a chunk of their production budget. That said, the production team hedged their bets by employing the services too of Rocky Taylor, Connery’s regular stunt double. The plan being to get a further ten minutes of footage that way.

It was difficult, but work got underway. Yet something of a disaster meant extra expenditure. More money had to be found when a crane shot involving Connery – a complex setup – was filmed and processed, only to come back damaged. A scratch on the negative had rendered it completely unusable. That whole shot thus had to be setup and done again, with the already tired crew’s day off cancelled one Sunday. Fortunately in the end, the insurance agreed to cough up the funds for reshoot.

Yet also, Connery agreed to work over for free one day to get a particular speech in the can too. In fact, Mulcahy would go on, in the aforementioned Film Review piece, to say that Connery was a lot more fun to work with on the second film (having won his Oscar for The Untouchables between the two movies). Some crew members had still been nervous about working with Connery, and on his first day, there was reportedly a lot of tiptoeing about. One crew member was apparently so keen to make a good impression with the actor that she ended up calling him “his Sean-ness”.

Connery for his part would insist that “anybody who’s professional has no problems with me”, and that would bear out. He and Lambert in particular were said to have got on very well.

But in spite of jumping through the assorted hoops to get Connery involved – and to get the movie itself completed in very, very testing circumstances – the film itself would stumble. The box office returns, following the bloating of the budget and the critical evisceration of the movie, were below expectations and hopes. It’d over time cover its costs, but only just.

This time, though, there was an olive branch for Highlander, in the shape of a television show that’d earn far more acclaim and a lot more success, debuting in 1992. It’d also re-ignite the franchise, and to this day, chatter continues of even more films to go with the six made to date (a reboot has been in development hell for years).

As for Connery, his time in Argentina would be his last on the Highlander franchise. And Ramirez would remain the only character – outside of James Bond – who he played more than once on the big screen…

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