Havana, Cuba, 1959 and there are some new arrivals in the country's capital today. On the same aeroplane are Major Robert Dapes (Sean Connery) a Brit who is being brought in unofficially to assist the ruling Batista regime in solving their problems with the brewing revolution of Fidel Castro, and Larry Gutman (Jack Weston), an American businessman who thinks he sees an opportunity for profit here. They both have an interest in being there, but Dapes has another for fifteen years ago he had an affair with the Cuban Alexandra (Brooke Adams), and she happens to be in the city - the trouble for the Major is she's married.
Cuba, the film, was a troubled production with an equally troubled release, mainly because it set itself up to be nostalgically reminiscent of the classic Casablanca, but in effect was the anti-Casablanca when nothing in the plot works out romantically or heroically. This was one of the movies of Richard Lester where he took a long look at big screen heroism and found it lacking, making for an effort which may have suited the seventies, but was being put out just as the decade turned to the far more gung ho eighties, leaving it all at sea when your typical action flick of the day was far less complex in approaching its manly men protagonists. Perhaps that was the reason Lester and his star fell out in the making of this.
Mind you, given the script wasn't finished when they began shooting it's little wonder there may have been certain tensions. Not helping was an end result which when both critics and audiences got to see it left them baffled, trying in vain to work out some kind of plot or the state of play between the character relationships and finding it all fatally murky, blaming Lester for losing his grip on the work and allowing it to get out of hand. Yet when a director of a more recent vintage, self-confessed Lester fan Steven Soderbergh, began to champion Cuba as a flawed masterpiece some, not many, but some opted to give it another go, and it was true it was a film which improved on second viewing as you would have a better idea of what the goals were.
There's very little pulse pounding about the adventure here, not to mention the romance, the latter easily summed up as Alexandra telling Dapes that she wasn't some idealised lover for him to carry away from all this in his big strong arms because she has other, more independent paths to travel herself; she likes being in Havana no matter how dangerous it is getting and if that's a mistake it's hers to make. As for the former, there were certainly sequences where bullets flew and people shouted and ran and explosions were set off, but Lester kept a watchful distance from this, even ironically noting at points that simple one man against an army fearlessness isn't going to count for much in the confusion of actual conflict, and that included random terrorist activity.
There's a particularly grim scene where a genteel dinner party of the Havanan rich and powerful is brutally interrupted by machine gun-toting rebels who lay waste to about half of them before rushing off as quickly as they arrived. Dapes isn't even in the building when this happens, and shows up after it's over, trying to help and finding the survivors more interested in themselves than the other injured. The question about whether this was pro- or anti-Castro and the revolution could be summed up in this in that basically you could read it either way as the characters seem weirdly reluctant to engage with the issues, as if in denial about the massive upheaval fast encroaching on their lives, and this narrative neutrality could be another reason few got on with the film at the time. There's also a strange, distant mood where the settings seem to be curiously empty even when there are people around, as if reflecting their mindset and anyone trying to embark on a meaningful connection is doomed to chaos. Music by Patrick Williams.