While many nostalgia and period pieces about the 1960s were released in the 1990s, few were aimed so steadfastly at the younger generation as Mermaids. Based on the young adult novel by Patty Dann, the story revolves around the Flax family – mother Rachel (Cher) and daughters Charlotte (Winona Ryder), and Kate (Christina Ricci) – over the latter half of 1963 and the first half of 1964. We’re first introduced to the Flaxes as they’re packing up to leave their home in Oklahoma, and as the action moves out on to the road, Charlotte, who narrates the film, paints a picture of a family on the move, and a mother who can never bring herself to stay in one place for very long. Whether because of professional dissatisfaction, romantic disappointment, or the general restlessness and wandering spirit of the 60s, it’s only a matter of time before “Mrs. Flax” – as she is always referred to in Charlotte’s narration – decides that it’s time to move on to the next town and the next adventure. While Kate is still a small child, and is fairly comfortable with the constant movement, Charlotte finds that the family’s itinerant lifestyle plays to all her teenage melancholic angst, always seeming to put more and more space between her and her long-lost father, even as it feels as if every change of location might draw him closer to her too.

When it comes to deciding where to move next, Mrs. Flax has a very simple method – she simply shuts her eyes and picks out a random point on a map of the United States. As luck would have it, she lights upon Massachusetts as the next port of call after Oklahoma – and so it’s only a matter of time before we arrive in Eastport, MA, the small rural town where the rest of the action unfolds. Over the late 80s and early 90s, mainstream American cinema specialised in creating bucolic visions of the small-town life that had been eroded in the wake of globalisation and the decline of local manufacturing industries, and Eastport is one of the most memorable of these confections. To some extent, that’s because of the particular pull that New England had on American nostalgia at this point in time, but it’s also because this particular small town doesn’t feel exclusively addressed to Baby Boomers anxious for an idealised and nostalgic version of their past either. While there is certainly an address to children of the 60s in the attention paid to pop music, costumes and period fixtures, the film, as a whole, is suffused with a bittersweetness that cuts across straight nostalgia – a soulfulness that feels drawn from the distinctive melancholy of what is often referred to as the golden age of American young adult fiction, a body of work that spans the 1970s to the the late 1980s, of which Dann’s coming-of-age story is one of the key novels.

Young adult novelists writing during this particular period – which included such luminaries as Katherine Paterson and Robert Cormier – were often Baby Boomers (or older) themselves, but their protagonists, crucially, were young people trying to navigate and make sense of the world in the wake of the Baby Boomer revolution, along with a world that in some ways had failed the promise afforded by the Baby Boomers in the first place. These young adult novels often addressed the strange silent space between the Baby Boomers and Gen X, along with the ways in which that shaped Gen X in turn, and often featured characters who were stifled, muted or debilitated in some form by the promises of the parental and paternal generation that had gone before them. While Dann’s novel does offer itself as a work of Baby Boomer nostalgia, then, it is even more directed at the legacy of that nostalgia for adolescents growing up in the 80s. That focus continues into the film adaptation too, thanks to the wholesale importation of slabs of Dann’s prose for Ryder’s internal monologues, turning the film itself into something of a late addition to this golden age of young adult fiction – a self-consciously literary and literate exercise in calibrating the adolescent precocity of the 80s and early 90s against its larger-than-life forbears of the 60s.

Key to that process, of course, is Ryder herself. While there can be no doubt that Ryder came to personify this strange silent space between the Baby Boomers and Gen X, and its impact upon Gen X melancholy and anxiety, it can be harder to pin down exactly how she managed to do so, or what gave her such cache. In part, that’s because she often seemed to offer a negative personification, or a negative characterisation, that was less about embodying a generation than embodying the sense of displacement that typified a generation, along with the sneaking suspicion that the teenagers she was representing would have fared much better as Baby Boomers – and perhaps might have been even more successful than Baby Boomers at sorting out the pitfalls of the 60s, if only, somewhat paradoxically, because they had the spectacle of declining Baby Boomers to learn from. Given that the Baby Boomers had effectively invented adolescence – or at least had been the first generation in which adolescence was a completely discrete category of experience – it was inevitable that the next generation of adolescents would feel somewhat displaced from that original moment, combined with a sense that the next generation had missed a formative opportunity to make good on the promise of adolescence as well. With an early career that alternated between teen films like Lucas and Heathers, and period pieces like 1969 and Great Balls of Fire!, it was only a matter of time before Ryder was cast in a film, like Mermaids, that would congeal all these tendencies into a fully-formed screen persona.

That she managed to do so, in Mermaids, is partly a testament to how fully Benjamin immerses us in Charlotte’s particular world, to the point where all the other period details, and Cher’s own reprisal of her 60s iconicity, are relegated to a muffled distance – not the muffled distance of straight nostalgia, but the muffled distance of second-hand nostalgia, nostalgia handed down as an oppressive legacy of the Baby Boomer experiment. For that reason, Mermaids has a curious timelessness, or feels curiously of its time, insofar as it feels set in the 90s more than in the 60s, offering up a scenario – a “radical” parent and “reactionary” teenager – that is probably a more accurate reflection of how family life looked at the end of the 80s than it did at the beginning of the 60s. As a result, this is also probably the film in which Ryder comes closest to playing herself, or to playing what she represented to her audience, since Mermaids feels less like a period piece than a demonstration of how a particular period had continued to make its presence felt to a younger generation. While the film made be nominally located in the 60s, then, it feels “set” in the 90s, and it is against this oddly dislocated milieu that Ryder’s oddly displaced screen persona and, in particular, her trademark soulful slouch, really starts to come into its own.

As a result, I’ve always found Ryder’s screen persona to be inextricable from Charlotte’s particular characteristics and the way in which they pit her against Mrs. Flax. As a simulacrum of her 60s self, Cher here plays a capacity for sensual pleasure and a optimistic radicalism that’s somehow unavailable to Charlotte, who is forced to frame her yearnings in much more ascetic and mystical terms. While those mystical leanings do align her with the 60s to some extent, the fact that they are framed as a specifically Christian mysticism also detaches her from the hedonistic exuberance of Cher, imbuing her with a different kind of introspection and angst – the agon that doesn’t necessarily come from resisting pleasure, but from the sense that all the best pleasures have been taken. It’s appropriate, then, that the closest that the film comes to a dramatic climax turns on Mrs. Flax’s seduction of Charlotte’s only love interest, a handyman who works at the nunnery located down the road, and whose appeal seems to stem more from his proximity to the nuns than anything intrinsic about his own personality and appearance. For the most part, he functions to draw us into the strange mystical sensuality of this nunnery, which recalls young adult films and series like The Princess Bride, The Dark Crystal and The Labyrinth in the way in which it stretches back to the medieval era to try to capture something of the abiding strangeness of 80s childhood (“it’s the last day ever…ever of this year”), while imbuing the entire film with something of a New England Gothic flavour as well. At times, it feels a bit like a companion piece to the Massachusetts transcendentalism of Gillian Armstrong’s Little Women, as the nunnery is gradually condensed to its central campanile, against which Ryder is utterly luminous, beatified by a camera that lingers and pores over her face but is never satisfied.

Where Mrs. Flax “doesn’t believe in ritual or tradition,” then, Charlotte has a deep and mystical fascination with all the traditions that appear to have been jettisoned from her family life, most notably the lack of a stable or traditional nuclear family structure that gives the film its momentum in the first place. Some of the most beautiful moments in the film are reserved for her aching, inchoate memories of her father – fragments that seem to descend upon her from another world as much as another time – while the biggest excursus sees her entering a fugue state and driving across Massachusetts to Connecticut in search of a “normal” family that can substitute for her own. However, this yearning for a long vanished paternal authority is most gorgeously dramatised around the assassination of John F. Kennedy, which forms the centrepiece and climax of the film. At first, the news plays to all Charlotte’s father-sickness (“I want to speak to my father…it feels as if there isn’t an adult left on the entire planet”) and, slightly later, leads to a whole series of speculations as to how he might have taken the news (“I miss my father…I wonder if he’s watching television. Maybe he’s in the jungles of Brazil and doesn’t even realise what’s happened”) as the assassination seems to transplant the action and the emotional kernel of the film into the present, as if to capture and evoke the epicentre of an ongoing Baby Boomer crisis that has not dissipated and refuses to be healed. Bookended by a classroom discussion of the pilgrims reaching Plymouth Rock and the subsequent broadcast of Kennedy’s speech about the Second Space Age, the tragedy seems to rock and displace time, transforming the Baby Boomer generation into a emblem of everything incomplete about the American Dream.

It’s also the assassination that prompts Charlotte to both question her faith and declare her love physically for the first time, as she retreats with her lover to the campanile and ravishes him with kisses, an experience that is quickly followed by an extended period of self-flagellation in which she not only berates her bodily urges but, martyr-like, takes the whole responsibility for the assassination upon her shoulders, while also assuming that she has become pregnant, despite not having removed her clothes once over the course of the encounter. In the way in which it presents the impact of the Kennedy assassination as skipping a generation and in its barely suppressed longing for an immaculate conception capable of restoring the Baby Boomer prophecy, it’s one of the most astute and moving depictions I’ve ever seen of this particular moment in American history. While most of this scene takes place in and around the campanile, it is also the one point in the film at which we hear about the original native inhabitants in the land, as European and Indian presences coalesce to displace space and time, spiralling Charlotte into the fugue state that propels her to New Haven, deep into the heart of the 80s nostalgia-image, in search of her father.

Still, for all that it contains these moments of ecstasy and agony, part of what makes Mermaids so memorable is that it never quite loses the quotidian, day-to-day vibe of its opening scenes. Soulful and sentimental incident may abound, but Benjamin never exploits them or lingers on them for long enough to disrupt the overarching sense of pace and momentum, while the lack of any clear moment of romantic or sexual catharsis for Charlotte means that the film never seems to come to any definitive conclusion or single moment of awakening. As a result, while the film may all be set in one place, it never loses the rhythm of being on the road, or loses sight of the possibility that Mrs. Flax might up and move and any moment, creating an incredibly buoyant and resilient sense of place that makes all the factors inducing the Flaxes to stay in Massachusetts feel just that little bit more precious and precarious, while ensuring that the film itself demands to be rewatched the moment you finish it. Even the most exceptional moments in the story never feel too far from the quotidian routines of this family, just because those routines are all about breaking established routines, or moving on from anything as soon as it starts to resemble a routine.

On the one hand, that gives even the most mobile and dramatic scenes a wonderfully cosy, lived-in quality, but it also means that the family’s gradual glimpses of a new stability is shot through with all the wondrous variety and sense of possibility that comes from being on the road. Key to that process is the way that the film never quite massages out or planes away Cher’s angularities – apparently she clashed with Benjamin on set, and her character never loses her spikiness either, making it hard to discern just how much we should like or love and preventing the film ever settling into any one groove for any sustained length of time. In that sense, Mermaids perhaps finally belongs with a film like Sidney Lumet’s Running on Empty in the sensitivity and deftness with which it considers how to remain true to the momentum and rhythms of the 60s while building a genuine sense of family and community – with the critical difference that Mermaids feels more directly aimed at a younger generation anxious to figure out how to conceive of social institutions, family life and romantic love in the wake of the lessons and frustrations of their Baby Boomer ancestors.