The Holdovers is a wonderful portrait of teaching, the most generous-spirited film of Alexander Payne’s career and rivals Sideways as the best film of his career too. In part that’s because it’s also Payne’s first period piece and takes place in 1970, at the beginning of the New Hollywood era that formed such a touchstone for his reinvention of independent cinema in the 1990s. David Hemingson’s extraordinary screenwriting debut takes place over two weeks at Barton Academy, a fictional boarding school in New England. Suffused with a New Hollywood melancholy and shot so as to resemble grainy celluloid, the film starts by introducing us to Barton, a venerable institution that has transformed from a centre of academic learning to a pipeline for the monied class over the last couple of decades. In the leaving assembly before the holidays begin, the camera pans over commemorations to previous students who fought in World War I, World War II and Korea, but none of the current generation have served in Vietnam, having relegated military duties to the working classes.

Against that backdrop Payne does what he does best – evokes the evolving relationship between a small group of people. Every year there are a number of “holdovers” at Barton, students whose parents cannot have them home for Christmas, and every year a teacher is assigned to watch over them. Even though it is not his turn, classics professor Paul Hunham, played by Paul Giamatti, is wrangled into doing the job, since he doesn’t have any friends or family to visit anyway. While he’s initially tasked with looking after a small group of holdovers, all of them end up making a late departure except for Angus Tully, played by Dominic Sessa, whose parents remain unreachable when the other holdovers gain permission to head off on a collective ski trip. Paul and Angus are left alone with Mary Lamb, the head cook, played by Da’Vine Joy Randolph, whose son has recently died as the only Barton alumnus to fight in the Vietnam War, his only opportunity to earn the money needed to go to university after school.

While Payne does a beautiful job of evoking all three characters, Giamatti is his muse and Paul is at the centre of the film. As a teacher, Paul treads the line between rigour and pedantry – he seems to be universally disliked by colleagues and students, and yet he does hold to a certain academic ethic that appears to have been largely discarded at Barton. He’s also a jumble of contradictions, stuffy but capable of self-deprecation, overly formal but essentially compassionate, much as Payne paints him with a lovingly naturalistic brush while still allowing space for some quintessential Giamatti shtick (the first sounds we hear in the film are Paul’s incredulous and eccentric vocalisations as he marks student papers). These contradictions crystallise around Paul’s relationship to Barton itself. He claims to love the ascetic nature of campus life but drinks himself to sleep each night and rails against the entitlement of the new generation of wealthy students even as we learn that he was unable to finish his degree at Harvard because one such wealthy student copied his work, claimed plagiarism himself, and had the backing of a financial-legal machine that Paul simply couldn’t match. For this reason, Paul never finished his degree, despite his admonitions to his students to commit to their work, and lives in trepidation that the current administration will realise he is not qualified.  

Such character traits make Paul a remarkably dynamic figure and lend his interactions with Mary and Angus a real veracity. What ensues often plays as an allegory for teaching itself, and for a transition that many teachers describe from seeing their vocation in academic terms to understanding it as a pastoral calling. Initially, Paul uses the holdover period as a pretext for implementing the classical education that he feels is lacking at Barton. With Christmas only two weeks away, he makes the initial cohort of holdovers adhere to a standard school schedule, along with extended study sessions, and a punishing physical regimen that involves long runs in the snow, since the gymnasium is out of bounds and the heat is turned off in the rest of the college, rendering it untenable for exercise routines. He also sells the Barton Christmas tree back to local townies, discarding it both an an example of Christian cheer and of the post-classical Christian world. Throughout all these endeavours he draws continuous analogies with classical culture, inevitably to the studied boredom of both Angus and Mary.

Nevertheless, over the two week holdover period, Paul comes to understand the inherent relationality of teaching, and reconceive of his job as a pastoral orientation to both colleagues and students. From a stickler for rules, regulations and procedure, he not only learns to be a mentor, but discovers mentorship as a process of decentring oneself and learning to listen to other people, hear them out on their own life lessons and perspectives. As a result, Mary and Angus both come into focus over the second act, not merely as a springboard for Paul’s own self-realisation but as beautifully etched characters in and of themselves. We learn that both Mary’s son and husband never lived to be 25, that she loves game shows, that she is the eyes and ears of Barton, and that she possesses a wry and ironic sense of humour. Likewise, we learn that, beneath his exaggerated attitude, Angus is a deeply vulnerable young man, that his father has been committed to a psychiatric institute for early onset dementia, and that his mother has remarried with little concern for his welfare. Paul’s own growth comes to a head at the end of a weekend in Boston, when he and Mary take Angus out for dinner, and attempt to order him a serving of Cherries Jubilee, the local speciality, for dessert, only to be told by a waitress that the dessert can’t be served to minors, even though the alcohol is all burned off. Faced with a reflection of his own former slavish dedication to rules, Paul joins with Mary to combine cherries, alcohol and flame in the carpark, and almost burn it down in the process.

These evolving interactions feel all the more precious for the way in which Payne and cinematographer Eigil Bryld capture the textures of being alone in an analog world. In the present, the tactile experience of loneliness is bound up with the feel of a phone in your hand and the sensation of scrolling through endless feeds. But Payne takes us back to a time when that introspective tactility was transplanted onto real space and time in a way that it just can’t be now. One of the most memorable scenes in the film sees Angus stealing Paul’s keys and making his way around Barton at night, wandering from the kitchens to the service corridors to peripheries he didn’t even know existed. This sequence is melancholy and buoyant at the same time, since Angus is neither quite exploring nor escaping but feeling out the contours of his isolation and introspection, giving it shape by way of the physical world surrounding him. In doing so, he turns his loneliness into something he can inhabit, attach to, and call his own, finding solace in his own space and time in ways that have shifted in a digital universe.

This embodied isolation also makes moments of connection more precious at both a spatial and temporal level. Spatially, the three characters inch closer and closer to each other’s lives, as well to the lives of other members of the community, a process reflected in their sojourns away from Barton – to the emergency room, to a Christmas party, and finally to Boston. As they all find their own idiosyncratic trajectories around the empty college they also come closer to each other’s nooks and crannies, as shared space mercurially shifts into communal space. Temporally, the experience of so much blank time allows the characters to inch closer and closer to each other’s routines, while appreciating the different paths that have brought each of them to this particular moment. This is particularly acute for Paul and Angus, who grow closer precisely as they refine their understanding of how they are each cemented in their own generational mindset. In one of the most beautiful scenes in the film, Paul devotes a large chunk of his own time to searching the school for Angus, who he finds in the music hall, playing Erik Satie’s Gymnopedies, one of the foundational texts of ambient music. All three of the characters exude their own ambient music here, filling out the contours of loneliness with beats and tics that, to paraphrase Brian Eno, are more than capable of being entirely ignored, but start to resonate when their companions pay closer attention to them.

In other words, The Holdovers exhibits the same tactile oscillation between closeness and isolation that once accompanied cinemagoing – and it is from a visit to a Boston cinema, when Paul suddenly realises that Angus is no longer sitting beside him, that the emotional core of The Holdovers emerges. Only just catching Angus stepping into a taxi outside, and only just learning en route to the psychiatric institution that Angus’ father is not dead (as he previously claimed) but suffering from early onset dementia, Paul is rocketed into the core of Angus’ inner life before the aura of the cinema has left either of them. Likewise, this pivotal moment at the cusp of the cinema returns in the climax, when Paul takes responsibility for Angus’ trip to the psychiatric institute, going so far as to say that he advocated for it, in order to ensure that his ward can remain at Barton, even though it means that he will be fired. Paul’s final moment with Angus occurs as he is packing up to seek out new horizons, write a monograph and free himself of the strictures of Barton. True to the film as a whole, this moment evokes the enormous distance between the two men only to contour the precious intimacy between them in both spatial and temporal terms. For it is unlikely that Paul and Angus will ever inhabit the same space again, much as Paul has already become a part of Angus’ past, and yet both factors make his enduring influence even more palpable. In these final moments, Payne offers a paradoxical truth of teaching – that teachers influence students in what will become their distant past, in a remote spatial outlier from their eventual lives, in a present tense and mise-en-scene that is inevitably fleeting and can only fully resonate long after it has come and gone, much as the full significance of this analog can only fully resonate from our digital present.