Curly Sue was John Hughes’ last film as a director, and it’s both his bleakest and his most sentimental work – in a word, his most dissonant. That’s all the more striking in that it is also his most programmatic film, or at least attempts to be. At the heart of it is a woman named Grey, played by Kelly Lynch, who has to choose between her upper-class boyfriend Walker, played by John Getz, and a homeless man named Dancer, played by John Belushi, along with his adoptive daughter Sue, played by Alisan Porter. Dancer and Sue live as grifters, pulling scams on richer folks, and moving from city to city. They meet Grey when Dancer pretends to be run over as she’s pulling out of her carpark at a corporate law firm. Shortly after, however, Dancer is actually hit by Grey, when she’s exiting the same carpark, and so she invites him and Sue back to her upscale apartment, where their presence makes her question her life.

From the outset, it’s clear that Hughes is attempting to depict a grittier Chicago than we see in his previous films – a world of all night eateries, pawn shops and junk yards, all set against the squalor of a Midwest winter. Much of it feels extrapolated from the homeless woman in Home Alone 2, or the bleak textures of Planes, Trains and Automobiles, except that there’s no longer any consoling fantasy of home to redeem it all at the end. Going even further back, Curly Sue recalls the fairytales of classical Hollywood, when the Great Depression was still in living memory, injecting an edge of bitterness into even the most feel-good fantasy moments. At times, this vision of Chicago also approaches the bleary desuetude of New Hollywood, as Hughes takes us through many of the same vistas that framed Ferris Bueller’s Day Out, including the carpark itself where Dancer is hit, but in a more minor and melancholy register.

Against that bleakness, Hughes offers us a forced choice between two figures, or scenarios, that were quite common during Hollywood at this time. Firstly Grey, who is really the protagonist of the film, falls squarely into the archetype of the inhuman professional woman. We first meet her telling a client how to grind her ex-husband into the ground, while proudly announcing that she doesn’t have a husband, a baby, or even feelings: “You won’t get emotion from me. I’m not an emotional person.” She has a PA to manage her romantic life, and a leading partner who continually reminds her of her singledom, enjoining her to think of her client’s marriage and kids, “things you wouldn’t know about.” As in Ferris Bueller, this shrivelled womanhood finds its counterpart in regular digs at effete male service staff, as if proper femininity had been leached by gay men, leaving corporate faux-women in its place.

Unlike Ferris Bueller, however, Curly Sue is never confident in its ability to offer a corrective to the situation. For while Dancer and Sue fall into the archetypes of family, hearth and home, they position themselves in such a cynical, manipulative and mercenary fashion that they seem to lay the entire sentimental apparatus of Hollywood itself bare in the process. It is as if the mechanics of Hollywood sentiment were paraded in full view, rather than tactfully dressed up in middlebrow affectations, which perhaps explains the way in which the film criticism community responded to it – with a virulence that was tantamount to disavowal. After Grey hits Dancer and Sue for the first time, they arrange to meet her at a restaurant, so she can make amends by buying them dinner. When she enters, father and daughter put their hands on their chin and stare wistfully into space, summoning the ghosts of Charlie Chaplin and Shirley Temple. This is all performance, yet when Dancer is left alone, later on, he adopts the same pose, despite the fact that nobody is watching. In moments like these, Curly Sue concedes that the sentimental-cynical manipulation of family values is fully automatic now.

Curly Sue thus starts off as a parable about men who are dispossessed, rendered homeless, by professional women – or, conversely, about women who have too much domestic space of their own. Everyone seems stunned by the size, or even the mere fact, of Grey’s apartment, whether it’s the doctor who lives downstairs, kisses her on the cheek, and laments that she lives alone, or Sue, who can’t believe that she needs so much space, so many clothes, or such a big double bed: “How come you don’t have any kids? You have enough dough for lots of them.” In response, Grey grows self-conscious about the amount of space she owns, which makes her feel more precarious, as a single women, in the broader spaces of her life. After she hits Dancer for the first time, she takes care to scrutinise the carpark upon getting into her car, in the same way the opening victim of a horror film might scan for a stalker or slasher.

Yet while Curly Sue may play into fears about professional women, it never quite congeals around its conservative message. That’s partly a reflection of the sheer baldness of the options we’re presented with here – evil professional women or manipulative family tableau. Both of these are cariacatured almost to the point of parody, making it hard to tell how seriously we’re meant to take key scenes, as when Sue reins in the extravagance of Grey’s enormous double bed by standing on top of it and singing “The Star-Spangled Banner.” Gradually, slapstick starts to intrude into the narrative, often puncturing the most sentimental moments, but not quite as a subversion effect or as light-hearted distraction – more as a way of processing the dissonance at the heart of the film’s forced choice between these two ridiculous archetypes. It makes sense that Sue herself is named after one of the Three Stooges, since Hughes often pulls back right when the conservative ideology is getting into full-gear for a more inane and braindead register that makes the tone quite difficult to parse.

All of this means that the film genuinely modulates into something considerably stranger than what it initially seems to be. For one thing, the head of Grey’s law firm, who initially seems synonymous with the voice of the film, turns out to be an antagonist, pressuring her to destroy a set of photographs so the husband of her client, a corrupt politican, can retain his property, children and job. Then, Dancer takes Grey on a tour of his Chicago, starting with a garbage bus ride around the city, and moving into a distant progenitor to Saul Goodman and Kim Wexler’s grift-romance in Better Call Saul. Rather than simply “learning” how the other half lives, Grey leans into the pleasure of the con, as she and Dancer crash a wedding, pretend to be guests, and both give speeches, before distracting a movie theatre usher by pretending to locate their tickets while Sue sneaks around the back and lets them in through the fire exit. Much as Grey and Dancer find common ground in the con, so their broad characterisation, and opposition, also starts to feel like a Hollywood con that Hughes can’t believe in anymore.

This leads to the centrepiece of the film – the film that Grey, Dancer and Sue con themselves into. It’s a Looney Tunes feature, which we only see reflected in the 3D glasses of an entirely full cinema that dodges, weaves, recoils and laughs in tandem. In other words the modernist cinematic crowd, the crowd of The Crowd, and Hughes’ paen to the movies as both the art of, and reprieve, from the hustle of American social class, right down to Dancer stealing popcorn and Coke from the couple next to them. Hughes may not be able to visualise class outside of the crudest of early 90s archetypes, but in this moment, with this crowd, he glimpses an affinity between poverty and cinema, that takes Grey and Dancer deeper and deeper into the Hollywood past as their date night proceeds, until they’re back at her place, leaning on her grand piano, singing “You’re Nobody Until Somebody Loves You.” Rather than address class, Curly Sue leans into Hollywood’s melancholy and reflexive inability to face class head on, as the couple intone that “The world is still the same, you’ll never change it,” pause for what feels like a change, but is only Sue continuing the song back on top of Grey’s huge double bed.

It’s a poignant synecdoche for Hollywood’s difficulties with class. Right when Grey and Dancer glimpse the horizons of Hollywood, the figure of the kitsch child has to foreclose it, collapse it back into the sentimental nationalism of her last rendition of “The Star-Spangled Banner” on this same bed. And that is the strange bind of Curly Sue – Hughes starts off by offering family values as a reprieve for America’s ills, realises he is trapped by them, but belatedly, leaving him nowhere else to go to in a film that becomes simultaneously more yearning, more cynical and more coldly mechanical as it goes on. No surprise, then, that it was the last film he directed, since it is late work in spirit, even if it didn’t come at the end of his career – a haunted realisation that all the questions his classic films “answered” were still wide open.