One of the most languorous and sumptuously atmospheric films in Sydney Pollack’s long career, Havana updates Casablanca for the early 1990s, by way of a period piece set on the eve of the Cuban Revolution. Robert Redford plays Jack Weil, a professional gambler who becomes embroiled with Roberta “Bobby” Duran (Lena Olin), the wife of revolutionary Arturo Duran (Raul Julia), after assisting her on the boat from Miami to Havana. From thereon, he finds himself more and more drawn to Bobby, even as he increasingly tries to extricate himself from the political situation gathering momentum around her and Arturo. As the film proceeds, Pollack sketches out a rich tapestry of Havana figures and institutions, some real and some factual, as Jack is forced to confront the legacy of his many years of wandering and his own status, as an American, in a country that is on the verge of reinventing himself. When Arturo Duran is abducted and – apparently – executed by the government, Jack’s concern for Bobby sees him immersing himself in the Revolution more than he would ever have thought possible, as well as revising the solitary, melancholy, hardboiled stance that suffuses his presence in the opening scenes of the film.

As might be expected from a plot that so closely resembles Casablanca and To Have and Have Not, much of Havana plays as a reflection on classical Hollywood, with Redford and Olin clearly channeling Humphrey Bogart and Ingrid Bergman respectively. In addition, Olin’s address and register often seems to be bringing Audrey Hepburn into the mix, as I found myself wondering whether these ghostly shadows of Bogart and Hepburn were part of what inspired Pollack to remake Billy Wilder’s Sabrina a couple of years later. Not surprisingly, then, cinema is the first common experience that these two characters stumble upon, since Bobby has only ended up in Cuba after failing to make it in Hollywood (she was inspired by Greta Garbo in Camille), while Jack is a fan of westerns, admitting that “I don’t know what they have to do with anything, but I like them.” While Havana might represent the very margin of their cinematic fantasies, that also makes it feels quite attuned to all the fringes of the American empire that were so precious to classical Hollywood around the late 30s and early 40s, exotic and treacherous in equal measure. Indeed, one of the stylistic achievements of the film is that, despite running for close to three hours, Pollack’s version of Havana never feels settled or stabilised, but is instead always becoming more marginal to itself, more collapsed into its imminent transformation.

In that sense, the opening scene between Jack and Bobby on the boat from Miami, and its dreamy sense of displacement, is a good precursor to the film as a whole. Invoking a whole range of 1950s romances set on water – Gentlemen Prefer Blondes, The Mississippi Gambler, An Affair to Remember – as Pollack not only establishes one of the instantaneous charismatic communions that galvanised classical Hollywood, but sets the entire film adrift in a kind of hypothetical, transitional space that never feels quite as tethered to history as you might expect. Within that space, Havana often plays as a commentary on New Hollywood as much as classical Hollywood, especially The Godfather Part II, which is also, in large part, set in Havana in 1958. While the address and lexicon might be straight out of Casablanca, then, the atmospherics are more oneiric and existential, as if a series of classical tropes were jettisoned from their original context and set amidst the heightened atmospherics and languorous melancholy against which Pollack and Redford both came of age.

Of course, by 1990, New Hollywood was hardly new, and so it makes sense that Havana takes place at a time when the very relationship between present, past and future was up for grabs. With most of the film occurring on the very cusp of the Cuban Revolution, it’s clear that some characters are already inhabiting the future, some are already consigned to the past, and some are still trying to negotiate both the futurity and pastness of the present, producing a state of flux that both Jack and Bobby try to mobilise in very different ways. On the one hand, Bobby, and Arturo, work to shape the impending sense of unrest into the revolutionary momentum needed to usher in a properly communist government, while Jack is aware that times of turmoil can be profitable to the professional gambler, and works hard to insinuate himself into the last remaining card games that are being played. With more and more people leaving the island every day, these games are only conducted amongst the wealthiest and most established people in Havana – or at least the most entrenched in their views – and so it’s no coincidence that these turn out to be some of the key players in the Revolution as well – both facilitating or resisting it – as the film proceeds.

Throughout these early sequences, it quickly comes to feel as if Pollack is both trying to envisage Redford in a classical Hollywood film and to pay some kind of homage to his New Hollywood legacy at the same time. In some sense, Jack is the only character in the film, and even then he is not quite a character but a series of stances that seem to search for some kind of common denominator between classical and New Hollywood on the cusp of the 1990s – the real fringe space that animates the narrative propulsion of the film. At moments, it is almost as if Pollack is trying to envisage what lies beyond New Hollywood, or what will be the next stage in the ongoing revision of classical Hollywood, which is perhaps why Havana often feels like an elegiac gesture as much as anything else, a way of enshrining and preserving the legacy of the 60s and 70s much as the directors of the 60s and 70s enshrined and preserved the legacy of the 40s and 50s. More specifically, this means that Havana is also Pollack’s tribute to his working relationship with Redford, and marks the last of their seven films together before Harrison Ford started to supplant Redford in Pollack’s filmography, much as Redford had supplanted Burt Lancaster before him.

Nevertheless, Ford and Lancaster were both bookends, since it was with Redford, who worked with him from 1966 to 1990, that Pollack moved from the late studio era to a full-blown New Hollywood aesthetic and finally, in Havana, to something beyond it. In that sense, Havana not only feels like the last truly New Hollywood outing in Pollack’s filmography, but one of the very last New Hollywood films full stop, with only Robert Towne and Jack Nicholson’s sequel to Chinatown, also released in 1990, coming close. It’s not surprising, then, that Pollack’s next two films (Presumed Innocent and The Firm) would be adaptations of contemporary potboilers, nor that he would only be able to return to both classical and New Hollywood from this point onwards through pastiche (Sabrina and The Interpreter), with Random Hearts standing out amidst all of these late works as his most anarchic and startling effort to craft a genuinely post-New Hollywood aesthetic. One of the biggest cues that New Hollywood took from classical Hollywood was its sense of disillusion, disenchantment and futurelessness, and yet the paradox of New Hollywood was that this very distrust in a future – or at least the future promised by the American government – was what guaranteed its such endurance and longevity. Something of that same paradox occurs her as well, with Pollack appearing to foreclose any further evolution of his style in the name of an ennui that seems suddenly and strangely pregnant, with Jack observing, in one key scene that “A funny thing happened to me last week, Joe. I realised I wasn’t going to die young.”

In the same way, Havana takes the hermetic hardboiled stance of the 1940s – and its stylised revival in the 1970s – and expose it to scenarios that seem to affirm and implode it in the same breath. Much of that revolves around Jack’s existential witticisms, which grow more brilliantly aphoristic with every scene, to the point where the film almost plays out as a series of superb one-liners. Given that most of these pithy observations evince a distaste and disregard for politics, the aphoristic and the apolitical quickly converge into the same mode of address, with Jack’s very style of delivery signalling his refusal to be bound by any of the revolutionary or reactionary movements that he sees escalating in the city streets around him. At the same time, however, Jack finds it harder and harder to maintain this foothold “outside” politics, as his hardboiled detachment comes to implicate him more than even the most modest investment in the events transpiring before him ever would have. After all, the film begins with him making the archetypical “apolitical” act of classical Hollywood – helping a beautiful woman in distress, regardless of her character or affiliations – only for him to spend the rest of the narrative trying to extricate himself from the escalating political ramifications of that opening act.

Pollack’s depiction of Havana therefore often seems to oscillate between Jack’s fantasy of Havana and the material realities of the city itself, or between Jack’s fantasy of abstracting Roberta from the city and her increasing inextricability from the city, with the streetscapes seem to personify both of them at different times and in different ways. On the one hand, this is a monadic, almost oneiric metropolis, perfectly suited to Jack’s proclivities, a city in which it initially seems possible for a man – especially an outsider – to remove himself from the world to focus purely and exclusively on his appetites. Not surprisingly, this incarnation of Havana revels in set design and Hollywood artifice, and yet as the film proceeds Pollack cuts more and more seamlessly between sets and location shooting, subsuming even the most monumental and theatrical set pieces into a wider and more anarchic burlesque texture that eventually buries his enormous sound stages in a tipsy, promiscuous, queer sensuality. Whereas the early parts of the film cut quite pointedly between bodies and streetscapes, it becomes harder to distinguish between the two as the story proceeds. By the third act, Pollack’s lithe, limber pans have completely internalised the rhythm of the heaving, intertwining bodies masses, as if to invoke a revolutionary crowd that has somehow worked its way into Jack’s most private, hermetic and solitary moments.

In other words Pollack only constructs such a lavish simulation of 1950s Havana for the sake of dismantling it – not, to be sure, in a destructive or sudden manner (there is no alienation effect here), but by way of an escalating porosity that renders it harder and harder for Jack to exempt himself from the events unfolding around him. It’s not just Pollack’s visuals that effect this either, but his beautifully curated soundscapes, whose ambient tones are just distant enough that Jack can’t fully fathom them, but just close enough to prevent him ever fully ignoring them either. At times, these subliminal snatches of melody seem to stand in for everything about the city that refuses to be contained or domesticated by Jack’s pithy one-liners, especially in the later parts of the film, when the nightlife decelerates and the revolution gathers momentum. For the first time, Jack appears to be presented with exactly the kind of silence and isolation he craves, even as the hush that settles over Havana also crystallises a more elusive and revolutionary openness that defies all his efforts to extract himself from it. In some ways, these later scenes are the most consummate parts of the film, with Pollack managing to capture the cessation of tourist momentum and escalation of political momentum in the same shot, as Jack tries – and fails – to position himself at the exact nexus between these two contradictory rhythms.

Of course, this awareness of being implicated – and complicit – in political events was always part of the trajectory of the classical hardboiled hero as well. Yet whereas that often encouraged the men of classical Hollywood to double down on their bitter disillusionment, here that isn’t really a possibility, since it simply ends up making Jack more enmeshed in the events he is trying to escape. Similarly, whereas the women of classical Hollywood tended to be inexplicable by virtue of their beauty, or some ineffable core of femininity, here it’s Bobby’s commitment to a cause that finally flummoxes Jack, especially when she demands pragmatic assistance in lieu of all his romantic efforts to save or redeem her. Even when they do finally engage in a fleeting romance, her ongoing refusal to differentiate between personal and political imperatives just intensifies her mystique for Jack, who at this point still seems to expect that she will consummate his search for a space outside politics, rather than embedding him back within it. No doubt, hardboiled Hollywood had no problem with a woman rousing a man’s ethical and political conscience, but it was rarer for her to do it from squarely within the field of politics itself, let alone to be an actual political revolutionary as she is here (she is the only person we see tortured), especially once Arturo is executed and she has to organise his troops herself.

That romantic tension, and the tension around what Jack expects from a romance, culminates with an incredible sequence in which he heads into the Cuban countryside in search of Bobby after she has fled from the city. As he moves through one war zone after another, he is presented by spaces that have just felt the brunt of the revolution – or are about to – as the rebels make their way towards the capital. For the first time in the film, his cool, calm, hardboiled haptics are utterly disrupted, as he is presented with victims of war, especially children, whose blank disillusion exceeds even his coolest and studied poses, rendering his own body language quite frantic and hysterical by comparison. Even or especially as Jack wants to engage with the political situation, then, he finds himself impossible to comprehend what he is seeing, with one of his American confreres reminding him shortly after that “This isn’t our business, it’s their business – you’re not poor, you’re not hungry and you aren’t Cuban.” Watching this scene, I realise that the detachment of hardboiled protagonists is premised on the assumption that they could engage if they want to – they just don’t want to – and that their melancholy demeanour is itself a sign of privilege, the privilege of being able to choose not to engage with the political process. By thwarting the very moment at which Jack chooses to shed his hardboiled shell, then, Havana refuses to allow him a moment of tragic or redemptive nobility and instead consigns him to an even more hermetic prison, a prison that is no longer of his own making.

In the process, Pollack offers a kind of revisionist neo-noir in which the hardboiled protagonist is trapped by his textual and affective legacy, building to an oddly atonal conclusion in which the Revolution is presented as a triumph of sorts, but a triumph that has left Jack behind, and has exceeded what he can comprehend. Concomitantly, the film makes it clear that this hardboiled stance will prove even more inadequate to understanding the events of the next few decade, with one of Jack’s contacts in Havana departing for Vietnam, and another world: “Indochina, where’s Indochina?” “It’s a long way away, Jack.” In these last few moments, if almost feels as if Pollack is trying to make Redford’s address and manner feel dated, with Roberta also observing, during these final scenes, that his perennial greeting of “kiddo” always felt old-fashioned, more at home in the 1920s than the 1950s (let alone the 1990s). While Havana may initially seem to approach the conclusion of Casablanca – Jack remaining but ferrying Roberta to safety – it takes a final, abrupt turn, as it is revealed that Arturo is in fact still alive and that Roberta will be remaining behind to assist his revolutionary plans, with Jack instead heading back to the United States alone.

From there, we move to an epilogue, set in 1963, in Key West, in which we see Jack waiting, hope against hope, for Roberta to arrive, as he reflects that “It’s a new decade – things are different. We got our own revolution going on.” By this stage, there’s no doubt that Jack is well and truly old, and yet this was also the period when Redford himself was starting to make his first inroads into cinema. As he is subsumed back into the matrix from which he initially emerged as an actor, there’s a beautiful and poetic sense of coming full circle, a final contemplation of how the world beyond New Hollywood might continue to be sustained by Hollywood, even if New Hollywood is in itself no longer adequate to that world either. In the most gorgeous utterances of the film, Jack’s aphorisms finally reach the splendid isolation they have been yearning for, even as they consign him to a genuine – and genuinely melancholy – irrelevance, as opposed to the hardboiled affectations of the opening acts. Just as Pollack reconstructs Havana for the sake of deconstructing it, so it feels as if he has only strained for the broad, novelistic sweep of New Hollywood (and The Godfather Part II in particular) for the sake of finally dissociating it into these last elliptical fragments, the perfect coda to the long 1970s in American cinema, and one of the most lyrical sequences in both his and Redford’s careers.