Days of Glory: The Myth of Nostalgia in The Holdovers

illustration by Tom Ralston

As far as prisoners go, Angus Tully doesn’t have it too bad. When his warden falls asleep at night, Angus drinks dark liquor out of an ornate goblet, shovels unrestricted amounts of ice cream into his mouth, skips down the hallways of a school where he typically comports himself like a grownup, and smokes with reckless abandon by a grand piano. In other words, he behaves exactly as a teenager does, veering between childlike desires and adult vices. While the analogy of imprisonment might seem extreme—Angus is just a student at boarding school—prisons and boarding schools both fit into the category of “total institutions,” after the work of sociologist Erving Goffman: “A total institution may be defined as a place of residence and work where a large number of like-situated individuals cut off from the wider society for an appreciable period of time together lead an enclosed formally administered round of life.” (Goffman lists hospitals and asylums as other examples of total institutions.) When Angus successfully blackmails his warden (Mr. Hunham, the teacher reluctantly tasked with caring for him), his request mirrors the liminal nature of teenagehood, too: he wants to go to Boston. The desire is both that of a child who dreams of the big city, and of an adult who recognizes on some level that total institutions make people into children—dependent on some higher authority—and wants to escape such a fate. 

Though I’m technically closer in age to Angus than to any of the adults in The Holdovers (2023), watching the film led me to sympathize with him from a distance and empathize more with his caretakers. I applied to work at boarding schools in my senior year of college with a very limited understanding of what that experience would be. Like most members of my socioeconomic background, I first learned what boarding school was through Harry Potter. As I got older, films like Dead Poets Society and books like John Knowles’s A Separate Peace and Tobias Wolff’s Old School further entrenched my idea that boarding school must indeed be a genuinely magical place, an alternate reality that did indeed exist somewhere out there. I read Old School every fall in high school, trying to imagine for myself what it would be like to go to school surrounded by people who cared about art and literature enough that they would commit acts of academic dishonesty just to get an audience with Ernest Hemingway. In applying for these teaching jobs, I imagined that my own students would be like that, and that I might also assume a John Keatings-esque position, imbuing them with a deep love for literature for the rest of their days. 

Three of my good friends in college had attended boarding schools. They all talked about their (different) schools, often. I could tell anyone, easily, where the three of them attended high school, but I’m certain that they could not tell you the name of my public high school. This isn’t a judgment on their character or listening abilities at all—it’s just that their high school experiences were more formative to their identities than mine were to me. Of all the people in my life, they were the most excited to hear that I had accepted a position teaching English at a New England boarding school, and were the most eager to start planning when they would come and visit me. “You’ll love it,” they said. “You should learn how to pierce ears with the back of an earring. That’s what we did in the bathrooms at night.” I reminded them that I would be a teacher and it would, in fact, be my responsibility to stop girls from doing that. But I, too, had already confused my desire to be a student at a boarding school with my desire to be a teacher at a boarding school. 

Alexander Payne’s The Holdovers is a unique entry in the boarding school genre, just as interested in the teacher experience of the institution as it is in the student experience. The film opens with three successive shots of its main characters: Paul Hunham (Paul Giamatti), a longtime teacher at Barton Academy, an all-boys New England preparatory school that he’d once attended himself; Angus Tully (Dominic Sessa), a current student at the school; and Mary Lamb (Da’Vine Joy Randolph), Barton Academy’s kitchen manager. The film primarily focuses on the relationship between Hunham and Angus as they spend Christmas break together: Angus expects, at the end of the semester, to head to St. Kitt’s for a beachy holiday with his family, but his mother and stepfather have instead left him to “hold over” at the school, under the supervision of his Ancient Civilizations teacher, Mr. Hunham, while they enjoy a long-awaited honeymoon. 

None of The Holdovers was shot on a set; rather, it was all filmed on location at various boarding schools in New England, and one public school. I am currently employed by one of these schools. The administration hosted a special screening of The Holdovers before the film’s official release date in honor of this; I elected not to go, claiming that I wanted to protect my Saturday night and not spend more free time surrounded by people that I knew from work, whether students or colleagues. I went to watch the film at the theater in town a week later, by myself, on a Thursday night, and ultimately regretted my choice. I wanted someone to turn to and gasp when there was an exterior shot of the library or the arts building, or when, in the final shot, Hunham pulls on to the state highway that I’d—we’d—spent countless hours driving up and down. When the lights went up at the end, I saw two coworkers at the back of the theater anyway. 

Perhaps the most apt thing a boarding-school-graduate friend said to me before I embarked on my journey was that I would be amazed at how the school would have everything I needed within its confines. And she was right. When I first moved there, I didn’t have to drive into town to buy a bike—a colleague had one they could lend me. The same went for a squash racket—there were extras lying around the courts—and as long as I bought my own snow tires, another colleague’s husband, a mechanic, could change them for me. There was generally little reason to leave campus, which made the campus feel like the entire world. There is a very specific logic to life at a boarding school that feels impossible to explain to outsiders, but makes complete sense to those inside. Whenever things like these happened, my friend and I would joke about the true totality of the institution.

Even as Hunham and Angus start to see one another as more than just teacher and student, and a significant portion of The Holdovers takes place away from Barton Academy, the total institution casts a shadow over their relationship. The pair makes an unfortunate jaunt to the hospital, then to a local pub. With Mary, they attend a Christmas Eve party hosted by another staff member at Barton. In their final excursion, Angus and Hunham take an overnight trip to Boston, dropping off Mary at her sister’s house in Roxbury along the way, setting the stage for them to get to know each other without a mediating presence. 

Still, the language of the total institution encloses them. Angus aids Hunham in telling an extravagant lie to an old classmate of Hunham’s, and then turns on him in a fit of adolescent outrage once they’re alone, furious at the hypocrisy of his teacher: “I thought Barton men don’t lie.” The unadulterated emotion in that moment is incredibly pure—newcomer Dominic Sessa plays it beautifully, with many reviewers of the film rightfully noting his natural talent—but the hypocrisy isn’t just that people shouldn’t lie, it’s that Barton men shouldn’t lie. There’s a duality to Angus’s accusation—the implied criticism of Hunham as a graduate of Barton himself, and of the example he’s setting for Angus, a Barton man in the making. Ultimately, Angus can only read Hunham’s lie through the lens of the institution that has indelibly shaped them both. 

*

Private schools are premised on exclusion, so most stories about boarding school are stories of belonging, of in-groups and out-groups, of who grants access to spaces for the wealthy and elite, or how that access is denied. Despite being set in 1970, The Holdovers mostly sanitizes its story of any of the explicitly discriminatory elements of elite private schooling at that time. One of the boys originally “held over” along with Angus is Mormon; another is Korean. A bully makes a crack about each of them that Angus quickly dismisses, and that’s that. The Holdovers mostly outsources its critique of power instead of looking inwards, at its own settings and characters. Mary spends much of the film grieving her son, Curtis, who didn’t have the wealth or resources to avoid the draft, and died in Vietnam. Every word spoken about Curtis’s experience at Barton, though, is one of praise, of how widely adored he was, how well he fit in. To the film’s credit, Mary’s character—a woman who carries on the daily patterns of life with humor and compassion despite her enormous loss—is fully realized, but the film only raises the larger question of her position within the institution through another snide comment from a bratty student, which Hunham quickly shuts down. 

The true concern of The Holdovers is what it means to pass as wealthy and elite, but feel, internally, like an outsider. As far as Barton men go, Angus and Hunham fit the standard bill pretty well as implied WASPs, though each of them reveals, over the course of the film, how he feels like an imposter. Angus has been expelled from several schools prior to his arrival at Barton, and his father, we later find out, has been institutionalized. Hunham, back in his day, attended Barton on a full scholarship and was later kicked out of Harvard on (false) plagiarism charges. For a film preoccupied with the role of Barton Academy in the lives of its protagonists, the inclusion of nonwhite characters in The Holdovers, and its simultaneous refusal to genuinely engage in their place at Barton, represents one of the troubles of making, in 2023, a feel-good American movie set in the 1970s. 

For the first year that I taught at boarding school, I dated a boy who was also in his first year of teaching at boarding school. A major difference between us was that he had attended a boarding school of similar or slightly higher caliber than the one at which he taught. He, too, talked about his high school experience constantly, now through the lens of his adult experience. When we spoke on the phone some days, I would mention some tradition at my school that seemed ridiculous (on a bad day) or heartwarming (on a good day), and he would murmur in assent to tell me about some corresponding tradition that existed at his alma mater. Mostly I felt grateful that I was not reliving high school every day of my life when I went to work in the morning. But other times, I would look at my students, or at my boyfriend, and think, I can’t believe you get to have this. This, meaning the endowment, the all-expenses-paid school trip to Tanzania, the indoor and outdoor ice hockey rinks and the planetarium, the John Legend performing at the ribbon-cutting of the new arts building. This, meaning an advance screening of The Holdovers. At the graduation ceremony last year, the speaker—an alumnus of the school himself—gave each graduating senior one thousand dollars to donate to a charity of their choice. I nearly cried when I went home that day. I would remember the extravagance of that gesture for the rest of my life, but I barely remembered my own high school graduation. I had spent the last nine months of my life in proximity to one of my childhood dreams, just to confirm to myself that I would never fulfill it, only ever be in proximity to it. All I could really hope for was to be a significant supporting character in the lives of my students. 

Hunham, on some level, recognizes that the stars of boarding school are the students, because he frames his initial decision to teach at Barton after leaving Harvard as a last resort. He accepts a position as an adjunct faculty member because he has nowhere else to go. Barton provided shelter to him when he was young, and when he is only slightly older, takes him in once again. The same is true for Angus, who refers to himself, in a moment of anger, as “stashed away” at Barton. But Angus is slower to acknowledge that the school also shields him from the neglect of his mother on one hand, and from the threat of military school on the other. I, too, might have been quick to say to others that I was teaching English at a New England boarding school—a place that seems like a relic from another time—as a kind of sociological experiment (“material for my novel” was my preferred way of putting it), but my school, and my job, also sheltered me from things I was scared of: cooking all of my own meals, paying my bills by staring at a screen all day, losing the community I had treasured so deeply in college. 

The price of admission to the shelter of the total institution might be twofold, if you are a certain kind of person. Not only do you give up part of yourself to the institution (Hunham confesses, “Barton is my life. I don’t know what I would do without Barton”)—but also, that sacrifice can divide you against yourself. When you’re in the institution, you feel like you don’t belong, but when you leave it, you realize that the outside world doesn’t make sense to you—or rather, that you don’t make sense to the outside world. Forebodingly, once, my ex-boyfriend told me that I could joke all I wanted about conducting a sociological experiment, but the longer I spent in boarding school, the more it would shape me. His own immigrant mother had said to him that she wished she hadn’t sent him to any fancy private schools, because now the gulf between their experiences was too wide, and they just couldn’t understand one another. He was right. The stories that I want to share with my family and friends outside of work require too much exposition for me to repeat every time, an understanding of what constitutes sit-down lunch or what dorm duty entails that only lived experience can convey. And that I recognize the interior and exterior shots of schools like Choate, St. Mark’s, Northfield Mt. Hermon, and Deerfield in The Holdovers—that seeing these places on film excites me—is its own piece of evidence towards my belonging. 

At the end of the film, Hunham leaves Barton so that Angus can stay. Despite his earlier confession, Hunham recognizes that, ultimately, Angus needs Barton—the protection of the total institution—more than he does. I said to my ex-boyfriend in a moment of cruelty that I would never send my own children to boarding school because I would love them too much. I struggled often with that thought for the first few months that I worked there. What kind of parent would send their kid away to be raised by strangers? I had just graduated college at the time; it seemed utterly ridiculous that I, a twenty-two year old, was now being paid to look after other people’s children (let alone the children of billionaires). But when I shuttled kids around in vans, and the sun was setting and there was no more noise in the backseats so I looked into the rearview mirror and saw that they had all fallen asleep, I understood, just a little better, that more people can love your child at the total institution, and sometimes better than they can at home. An old adage of teaching is that a good teacher loves the students or the subject; a great teacher loves both. As he takes a swig of whiskey before driving away from Barton Academy, Paul Hunham might finally have become a great teacher.