1. The arrival of a new world

Throughout this most intoxicating of 80s comedies, Ferris, Sloane and Cameron quiver on the verge of a world of images. Every scene is on the verge of becoming a montage sequence and every image is on the verge of dissociating from the rest of the film into a splendid self-referentiality, devoid of meaning or meaningful enough in itself, depending on how you look at it. The art gallery, with its collection of still images, most of which are abstract, shot in the midst of abstract white space, feels like the culmination of this world – a world in which images have replaced humans. As the sequence progresses, the gallery feels less and less as if it is designed for human consumption, and more and more like a space designed simply for the artworks to commune with and contemplate each other.

2. Heralds of the digital

The last step before the arrival of this new world seems to be an unprecedented fixation with looking, watching and staring. Throughout the film the characters are exhilarated and debilitated by the sheer number of things to see, and the autonomy and agency of images themselves. The gallery marks the point at which images start regarding people, just as the scene opens with Ferris, Sloane and Cameron being absorbed into a walking montage sequence. Sight is overwhelming, and the objects of sight are infinitely fractallated. When Cameron stares at Sunday Afternoon on the Island of La Grand Jatte, Georges Seurat’s pointillism suddenly reveals itself for what it always was – a form of pixellation.

3. The fragility and beauty of adolescence

Nowhere else in the film is the tremulous and fleeting power of teenage life so beautifully celebrated and undercut as in the mock-heroic poses with which Ferris, Cameron and Sloane confront the sculpture gallery. As the sequence proceeds, we move from painting to sculpture to the characters themselves, whose ironic distance is undercut by how much they already seem contained and sculpted by the gallery’s sightlines and spaces. They seem to be parodying the sculpture, but the critical distance of parody is impossible for them, undercutting their militaristic postures with something infinitely more poignant and fragile.

4. Leisure Rules

Fredric Jameson once wrote that the 1920s were the last time when American society enabled a conspicuously wasteful, ostentatiously decadent leisure class. The 1980s were the only time since then when the re-emergence of that leisure class really felt plausible – and Ferris Bueller’s Day Off revels in that plausibility. After all, Ferris isn’t escaping anything but the domestic and educational rituals of the richest suburban enclave in America at the time. He doesn’t yearn for freedom or mobility but space to expand and perform his leisure lifestyle with more decadence and abandon. Throughout the day, that commitment to leisure always threatens to stultify and stagnate the trio – it is only the incessant momentum of Ferris’ plans that prevents them from transforming into the relics of the aristocratic past into which they are briefly subsumed in this scene, artefacts in themselves even or especially as they try to differentiate themselves from the other gallerygoers with their edgiest and most stylised postures yet.

5. Love letter to Chicago

If Ferris Bueller’s Day Off is Hughes’ love letter to Chicago, then this is the perfumed kiss. Sears Tower may be sublime, the Chicago Mercantile Exchange may be spectacular, the shores of Lake Michigan may be tumultuous, but nowhere do you sense Hughes’ pure love for the city as deeply and romantically as you do here. In effect, Hughes has turned the whole city into an art gallery – by taking us deep within the Art Institute of Chicago, he suddenly turns every painting into a reflection and refraction of the city. For a moment, there, Chicago really was the centre of the world – and it still feels like it whenever I watch this sequence.

6. The end of American hegemony

Nobody could deny, now, that this is a racist, sexist and homophobic film. At every turn, Ferris, Sloane and Cameron encounter people who challenge their white entitlement. This isn’t a clever or knowing retrospective reading – it’s all there in Ferris’ direct, ironic addresses to the camera. But the film also yearns for an American whiteness that can include all these influences. Sometimes, as in the street parade, the results feel a bit dated. But the best sequences, and the gallery sequence in particular, suggest that this project of syncretic whiteness is already a thing of the past, already doomed to fail. Even as the Art Institute of Chicago is offered as the very best of twentieth century world art, it feels staid, claustrophobic – and the action has to move back outside once again.

7. The end of modernism

It’s clear that, for, Hughes, adolescent is a struggle between modernist and postmodern impulses, with postmodernism winning out. Taken in their totality, the artworks selected from the Institute’s collection trace a path from Gustave Caillebotte to Edward Hopper through Mary Cassatt, while the parade sequence takes us under and around Alexander Calder’s iconic sculpture at Federal Plaza. Combined with the plaintive score, they suggest a yearning for deeply introspective and irreducibly impersonal experiences that remain somehow beyond the reach of the characters, at least in any permanent way. However deeply they commune, a simple cut or shift of images is enough to break their reverie – and, sure enough, we’ve gone from the deepest solitude to the heart of the parade, a change so sudden that it feels as if we’ve been flung back into the heart of the Mercantile Exchange. That cut is my favourite in the whole film.

8. American Windows

Pablo Picasso is reported to have commented that, when Henri Matisse died, Marc Chagall would be “the last painter left who understands what colour really is.” And Hughes’ hyperactive, montage-driven, MTV-styled colourism certainly feels like a way of crafting an aesthetic commensurate to Chagall’s American Windows, against which Ferris and Sloane share a kiss, in the only utterly unironised moment of romance in the entire film. Commissioned by the Art Institute of Chicago in 1977, there’s no more poignant symbol than these windows for the legacy of modernism in America, the wealth created by its immigrant culture, and the American preoccupation with enshrining and canonising a religious and revelatory version of itself that perhaps never actually happened. A year before the film was released, Chagall died just before completing another Chicago project – a tapestry for the Rehabilitation Institute of Chicago – and all the elegiac historicity of his stained glass works seeps over into the film in the wake of his passing, freezing Ferris and Sloane into the emblems of a good life that only seems destined to last the length of a single day, which is, of course, why you need to rewatch and relive that day over and over again.

9. Compulsive return

More than any other sequence in the film then, the depictions of the Art Institute of Chicago testify to the way the film compels you to revisit it: they are the driving force and motor engine for the film’s rewatchability. The still point around which the rest of the film revolves, they offer a world in which you can never look at something enough – what Richard Roeper described as “one of the highest ‘repeatability’ factors of any film I’ve ever seen…I can watch it again and again” – suffusing Hughes’ mise-en-scenes with a calm that deepens and a complexity that heightens the more time you spend with it. At heart, this is an ambient, new age film.

10. Dream Academies

Few directors knew how to tap the revelatory potential of the synthesizer like John Hughes. While there’s no doubt that his films became synonymous with big hits – “Don’t You Forget About Me,” “Subculture” – it was with the Dream Academy that he really found his muse. Sure, they contributed big hits of their own, but it was their short instrumental refrains, and their taste for the transcendence of small synthesized bridging sequences, that made them such a perfect complement to his powers. You see it in their instrumental riffs on “Power to Believe” in Planes, Trains and Automobiles, and it’s here in this short sequence as well, which moves from guitars to synthesizers as if to capture a world on the very verge of simulation, or a world on the very verge of recognising its simulation. At the same time, this transition never feels complete or assured – unlike Simple Minds and New Order, the Dream Academy used the synthesizer with tremulous hesitation, never quite losing that sense of a first leap into the digital void. In its aching beauty and heavenly chord progressions, their cover here of the Smiths’ “Please, Please Let Me Get What I Want” is the musical equivalent of the poses of Ferris, Sloane and Cameron: emphatic at first glance, they shiver, shake and betray themselves more and more with each viewing, until every other art work seems to tremble in the same way, with a barely suppressed longing to betray their human traces once again.