Francis Ford Coppola’s second film, You’re a Big Boy Now, was a major step forward from Dementia 13, and still feels like one of the most personal and spontaneous films of his whole career, especially in contrast to the stately classicism of his 70s output, and then the stagnant classicism that settled over much of his 80s output as he tried to recover his heyday. Based on the novel by David Benedictus, the film follows Bernard Chanticleer, a young New Yorker played by Peter Kastner, as he moves out his parents’ house and tries to find love and meaning in New York in the midst of the swinging sixties. His father, I.H., is played by Rip Torn, and runs the Incunabula section of the New York Public Library, while his mother, Margery, is played by Geraldine Page, and constantly worries about Bernard’s fate when he arrives in the Big Apple. Yet while both parents maintain some hold on their son after he moves into a rooming house owned by Miss Nora Thing, played by Julie Harris, he quickly discovers two potential love interests – Barbara Darling, a member of the New York artistic underground, played by Elizabeth Hartman, and Amy Partless, a school friend who now works in the Incunabula section of the New York Public Library, played by Karen Black.

As this rich cast might suggest, You’re a Big Boy Now is very much a film about generational shifts, directed at the first generation where they was no real expectation or illusion that young people should save themselves for marriage. The opening shot of the film foreshadows this generational divide, starting in the reading room of the New York Public Library, where a decorous silence, stylised symmetrical composition and stately pan down the middle aisle quickly gives way to polymorphous mechanics that take place behind the scenes. As the theme song of the film – “You’re a Big Boy Now,” by the Lovin’ Spoonful – ushers in the credits, we enter a zany world of pneumatic tubes, roller skates and dumb waiters that force the library workers to contort their bodies into ever more perverse and unlikely positions to service the silence upstairs, which is most pronounced around I.H.’s office. From the outset, Coppola not only creates a pointed contrast between the raucous sensuality of the post-war generation and the staid conservatism of the pre-war generation, but also suggests, more provocatively, that the pre-war generation is just as perverse in its own way – or at least depends on the same perverse impulses that drive the younger generation, just as the serene reading room depends on the polymorphous activity below.

Since Bernard works downstairs in the library, his need to distinguish himself from his father, and move out of home, initially plays as his need to dissociate himself from the library. Indeed, we only get a small glimpse of the library during these opening moments, which culminate with Bernard questioning whether to call I.H. “Father,” “Dad” or “Daddy,” before seeking respite in New York City, where he can finally escape the nickname of “Big Boy” that his parents insist on attributing to him. Both big and a boy at the same time, Bernard is oppressed by the arrested development of the baby boomer generation, seeming at once too old and too young for his age, especially whenever his parents are present. Restless to remake the world around him, and escape the categories of his parents’ generation, his first precious forays into New York City suffuse the film with a frantic, picaresque sense of space that makes this one of Coppola’s brightest, breeziest and most vivd efforts, which is perhaps why it sometimes seems to exude the momentum of a television series, or some other serial format that could extend exuberantly and indefinitely.

Initially, Bernard finds himself playing around with official language in the city, simplifying the names of things or imagining that abbreviations and acronyms have different meanings. For the first part of the film, we follow him as he creatively appropriates and repurposes the signage of the Big Apple, often by revealing the deeper assumptions lying beneath apparently benign or neutral phrases that are part and parcel of the everyday urban lexicon. At one point, he imagines the sign to a W.C. as standing for “war crimes,” and then “welcome communists,” as if to envisage a subway bathroom as the repository of all the most abject and scatological fears in American culture at this point in time. At another point, he sees that someone has scrawled “n—-rs go home” on the subway, and then lapses into a chain of surreal associations in which he recalls that “home is where the heart is,” but also that his “heart is in the highlands,” leading to a bizarre dream sequence of African-Americans parading across the Scottish moors in kilts – a feverish vision of the hallucinatory and heightened performance of whiteness that black folk had to endure in order to be taken seriously within the cultured New York spaces Bernard moves through in these first scenes.

Through this constant wordplay, Bernard adopts a provisional, cruisey line of flight from the received wisdom of the time, which Coppola finally visualizes as a series of long, ambling walks around New York City at night. These walks are the most accomplished part of the film, and still one of the high points of Coppola’s career, and crystallise around the peep shows and adult cinemas in Times Square, which become the starting-point for a new kind of cinematic language, not unlike the mercurial cityscapes of the French New Wave. Bernard first meets Amy here while his tie is caught in a film reel at a peep show, ushering in a hushed romantic sequence in which whispered conversations slip in and out of the diegesis, anticipating the complex soundscapes of The Conversation, and its fixation with hiding in plain sight in the midst of a massive metropolis. Here, however, Coppola is considerably more optimistic, envisaging Times Square as the site of a new kind of mediation, and a place where the conventional distinctions between diegetic and non-diegetic sound, and between onscreen and offscreen space, have collapsed, gesturing towards a post-cinematic futurity.

Accordingly, Bernard romances Amy by mediating their conversation through the Times Square nightscape in increasingly ingenious and beautiful ways. At one point, they talk from adjacent phone booths, at another point they watch themselves watching themselves – “See Yourself on Television” – outside a store with a live camera feed. When they have their first kiss, Times Square lights up in synergy, while their body language imperceptibly fuses while silhouetted against the never-ending backdrop of windows and entrances, most of which are selling some kind of quasi-cinematic spectacle. During these gorgeous scenes, Coppola reimagines the screwball project of rehabilitating marriage for a post-war era. No longer, as in the screwball era, can marriage be restored by retreating from the city, or from within the realms of analog media, as occurred in so many of the great newspaper dramas that comprise the screwball canon. Instead, romance can only be revived through the mercurial eroticism of a new and more provisional notion of what media entails, epitomised here by the flickering of surfaces, signage and interfaces across the Times Square landscape.

In order to evoke this landscape, Coppola remediates his own first film, compressing Dementia 13 into a series of images that are projected onto the walls of the rave where Bernard first encounters Barbara. Stripped of their original context, the free-floating images flicker in the background as the Lovin’ Spoonful plays the film’s soundtrack live, unfolding as multicolored bodies dance and writhe in stark contrast to the black-and-white print. In Dementia 13, Coppola offset Gothic horror, and its reliance on strong sequestrations of diegetic and non-diegetic space, with a more amorphous and ambient slasher potential. Here he takes that process of diegetic devolution a step further, as Dementia 13 literally and materially becomes the zone at which diegetic and non-diegetic space merges, since Coppola’s own shifting camera angles sometimes immerse us back into the events of his first film, but just as often flatten them into a mere ornament to the scene playing out here.

In other words, the residual classicism and conventionality of Dementia 13 is now deflected into a new multimodal happening that muddles diegetic boundaries, as Coppola intercuts images from his first film into his second, while interspersing them with overexposed and oversaturated images that turn the film strip itself into a key component of the spectacle. Beyond a certain point, it becomes impossible to separate the naturalism of the film from the materiality of the film strip, as Coppola uses this happening, and the Times Square nightscape, as the starting-point for a journey across the city in which he tries to involute and invert everything we know about New York from cinema – to turn it inside out and shoot it from angles we’ve never seen before. This urban reinvention corresponds to the elastic space, for Bernard, between “Daddy” and “Dad,” which grows more diffuse as the film proceeds. The further he gets from I.H.’s influence, the more buoyant his passage across the city, and the less hampered by the usual channels and trajectories. In one of the most beautiful and exuberant scenes, he loses a kite in Central Park, and chases it with glee, moving fluidly across every conceivable demographic and activity, turning Central Park into a line of flight from the city, a site where he can continue Times Square into daylight hours.

As the film proceeds, Coppola fixates on Barbara as the harbinger of this new media image, continually surrounding her with reflections and refractions of herself, and framing her with prostheses, part-objects and eccentric décor that prevents her presenting herself in a stable or static way to Bernard. We first meet her in the library, where she works, at the epicentre of all its polymorphous communication systems, before Bernard glimpses her dancing in a glass booth at the Dementia 13 happening, and then seeks her out in an experimental play that blurs the distinction between stage and audience. Gradually, Coppola’s lines of flight from conventional depictions of New York also constellate around Barbara – Bernard imagines himself walking in Times Square while composing his first letter to her, while his first letter from Barbara ushers in his most exuberant trajectory yet, sending him out into streets on roller-skates where the letter flies up into the air, mirroring the passage of the kite across Central Park earlier in the film. Like the kite and the letter, Bernard responds to Barbara with a buoyant energy that seems to expand space above and below him until he is almost floating, cruising through a virtual city that recombines the familiar sights and sounds of New York into a neon fever dream that is always contiguous with Times Square.

This eroticized urban texture culminates when Barbara undresses for Bernard for the first time, as Coppola reverts to the same handheld spontaneity, fluid camera work, and semi-continuous jump cuts that accompany Bernard on his nocturnal walks through the city, as if to condense the flickering, fugitive images of a new media regime to the threshold of Barbara’s body. Yet unlike his first two exploitation films, Coppola doesn’t simply treat women as a spectacle, devoting the second half of the film to Barbara’s perspective, and to the events that led to her appearing in happenings and experimental plays in New York. Coppola is particularly interested in Barbara’s time at boarding school, where she learned to love film – she considers it the most important part of her education – but also learned older men would do anything they could to exploit her, starting with one of her educators.

In other words, Barbara learned two critical lessons from school – to love film, and to distrust an older generation of men – motivating her to free cinema from the previous generation, and reconceive it as a happening, an event that takes place in a broader public sphere. Like Bernard, Barbara is searching for a new way to mediate desire that is both cinematic but that also exceeds the spaces of traditional cinema, not unlike the involution of Dementia 13 from a discrete screening to a more indiscriminate event. Between these two characters, Coppola himself tries to bring the immediacy of the city into the cinema, and the intensity of the cinema into the city – to make city and cinema porous – resulting in a remarkably immediate experience that still feels unique in his filmography, which is now better known for the stately classicism of his 70s work, and the often turgid ways in which he tried to revive that classicism in the 80s and 90s. In its own way, You’re a Big Boy Now feels more modern than anything he has produced since, so it’s disappointing that it seems to be one of his most difficult films to access, and one of the least viewed in his catalogue.

That’s not to say that You’re a Big Boy Now feels incongruous exactly, since it establishes many of the concerns with post-war masculinity that would filter into The Godfather trilogy, The Conversation and Apocalypse Now. Yet Coppola’s second film is arguably even more irreverent and playful – less angst-ridden – about the intense masculinity that preoccupies these later films, condensing their macho impulses into the rooster that lives on the top floor of Bernard’s boarding-house, and who only attacks attractive women. Like the house itself, this rooster is an arcane residue of pre-war masculinity, and indeed was raised before the war by Miss Thing’s family, who believed a woman should be chaperoned on early dates with a man – a lesson she tries to pass on to Bernard as he pursues his dual romances with Barbara and Amy. To some extent, Miss Thing’s relationship with Bernard is gradually displaced by Barbara, who becomes a kind of maternal figure, as Coppola anticipates The Graduate by falling back upon a mother-son relationship in lieu of any real certainty about how post-war masculinity should look. Like Faye Dunaway’s character, Barbara treats Bernard as a case of arrested development, preparing him milk and accidentally trapping him under her bed, but her attitude is ultimately more schizoid, as she alternates between comforting Bernard as a son and chastising him for his infantile disappointments as a lover.

The net result is that You’re a Big Boy Now never settles into the liturgical nostalgia for pre-war masculinity that characterises The Graduate, no matter how much this might seep into the stylised palettes of the first two films in The Godfather trilogy. Instead, Coppola maintains his line of flight from conventional masculinity right up until the brilliant final twist, which reveals that the older generation was always just as libidinal and polymorphous in its desires, meaning that the younger generation doesn’t even have to go through the angst of defining itself against its forebears. Initially, Miss Thing seems like a paragon of old-world femininity – her boarding house could easily be the backdrop for a family-friendly series – but our last glimpse of her is in a steamy embrace with a policeman, knocking down the photograph of her father that hangs above her bed in the midst of their love-making. Fatherly law and civil law give way to a rampant sensuality that only intensifies with Bernard’s final confrontation with his father, when we learn that the majority of his Incunabula is in fact rare erotic,a and that I.H.’s career at the New York Public Library amounts to curating, maintaining and oneirically relishing his own private stash of content.

Given that raucous conclusion, I wasn’t quite sure how to read the film’s final turn, in which Bernard ends up choosing Amy over Barbara. This is effectively presented as a spatial choice, as we return to the night walks that Bernard initially had with Amy, while leaving  Barbara with a magnificent chase scene that takes her and Bernard through every conceivable nook and cranny of a giant department store. While Amy is physically situated in Times Square, Barbara seems to embody Times Square’s energy in her zany and eccentric trajectories, which often reminded me of the oblique urban passageways of the French New Wave, and of Louis Malle’s Zazie in the Metro in particular. Add to that the fact that Amy is considerably more conventional than Barbara, and it’s hard not to feel that Coppola has retreated from the originality of his vision – or was forced to retreat – in the final few seconds, meaning that You’re a Big Boy Now ends up fleetingly prefiguring many of the elements in Coppola’s subsequent work that it initially seems so remote from. Still, it remains wonderfully fresh and spontaneous in its vision of a new romantic media – the smiley face that Bernard traces on the side of a phone booth like an inchoate emoticon – and one of the most underrated and gorgeously original films in Coppola’s body of work.