A Roman Holiday — The Holdovers

William J Hammon
11 min readNov 12, 2023

It’s been a long time since we’ve had a truly great movie set at Christmastime that can be viewed as both a holiday treat and something to enjoy the rest of the year. A large part of that is due to the over-commercialization of the season, obviously. Year in and year out we get an absolute plethora of yuletide fare that’s little more than thinly-veiled commercials or part of an ongoing genre brand like Hallmark movies. But also worth mentioning/blaming are people like, well, me.

I fully admit that I am a cynic when it comes to a lot of the pomp and circumstance around the proceedings. I often cringe at the treacle, I scoff at the religious grandstanding that some engage in to advance culture wars, and due to a lifetime of critical thinking habits triggered at a much earlier age than most, I second-guess the motivations of just about everything that comes out. I do my best to keep myself in check, but as I get older it becomes harder and harder to take things at face value and just enjoy the spirit of it all. That’s why some of my favorite holiday films (apart from It’s a Wonderful Life, which is an entire essay about my worldview unto itself) are the ones that use Christmas as more of a backdrop for different genres to have fun (films like Home Alone, Die Hard, Batman Returns, and most recently Violent Night) or that highlight the not-so-happy aspects, acknowledging that for many, this is not a joyful period ( Bad Santa, Scrooged, any version of How the Grinch Stole Christmas apart from the 2018 Illumination debacle). I adore the holiday season, as it’s the source of so many great memories, but I also know that there’s a lot of chicanery and bad faith actions behind some of the aspects we treat as normal. This is one of the myriad ways in which I can be a walking contradiction at times, but it’s also why I appreciate something that at least feels earnest all the more.

This brings us to Alexander Payne’s latest film, The Holdovers, a continuation of the director’s motif of depicting — both for humor and for serious examination — the sad underpinnings of our society. Through satirical works like Election and Downsizing, as well as brutally honest character studies like Nebraska, About Schmidt, and The Descendants, Payne has made his bones by showing us the, er, pain, behind the American Dream, so it’s only natural that he’d tackle the conventions of the Christmas movie with the same degree of scathing humor and dedicated humanism. Like many of his previous projects, privilege and entitlement directly clash with the realities of the world and the people who exist outside of the glossy ideal, with catharsis (and the eventual holiday warm fuzzy feelings) coming from surviving and carrying on rather than overcoming manufactured obstacles.

The lightning rod for this particular story is Paul Hunham, played by Paul Giamatti (who also headlined Payne’s 2004 hit, Sideways) in a nomination-worthy performance. Hunham is a classics teacher at the prestigious Barton Academy, an all-boys prep school filled to the brim with the scions of the powerful and influential. A curmudgeonly stickler for rules and academic standards, Hunham has run afoul of the administration countless times for his refusal to provide special treatment for the sons of donors and legacies, the most recent of which was failing the offspring of a sitting U.S. Senator, causing the boy to lose his acceptance to an Ivy League school. Hunham believes in molding future leaders rather than just giving them a pass, like the previous headmaster who mentored him when he was a student there, while the current top man, Hardy (Andrew Garman), who was also a former student, cares much more about the school’s endowment fund.

As the winter break approaches, Hunham is unofficially punished with babysitting the titular annual group of students who stay behind at the boarding school rather than going home to (or on vacation with) their families. Normally the sad duty is assigned on a rotation, but this year’s “winner” fakes an illness with his mother, saddling Hunham with the job since he basically never leaves campus anyway, even during the summer months. Clearly, he’s not happy, though as the film quickly establishes, he rarely is.

Also none too pleased is Angus Tully, played exquisitely by newcomer Dominic Sessa. As the movie begins, Tully is shown to be just as much of an entitled shit heel as the rest of his classmates, but at least he’s smart enough to earn some leeway by getting good grades, evidenced by a scene where he receives a B+ on his exam in Hunham’s class while the rest are at a C- or below. He’s not brilliant by any means, but he gets by and does his best to only rock the boat occasionally, especially as his new stepfather (Tate Donovan) is dangling the threat of military school over his head should he slip up. Still, he looks forward to a Caribbean getaway for the break, only to have that hope of respite dashed as his mother (Gillian Vigman) blindsides him with news that she’s cancelled their trip in favor of a honeymoon with said stepfather, leaving Angus behind. To make matters worse, after a few days one of the Holdovers (Michael Provost) is picked up for a ski trip by his parents, and everyone else is invited to accompany. But since Tully’s parents are unreachable in the tropics, he can’t go with, making him the sole student left at Barton. Going from the promise of sandy beaches and sunshine to a fortnight with the most hated teacher in his practically snowbound school in the span of three days would set anyone on a spiral.

The only source of comfort for either side is the school’s head cook, Mary (Da’Vine Joy Randolph, providing much of the film’s pathos effortlessly). Coming from an extremely poor family, she took the job at Barton to help ensure that her son would get in to the exclusive institution, and he excelled there before tragically dying in Vietnam. As such, she’s left as a living example of all that might have been. Yet somehow she mostly conducts herself with good humor and gratitude, even when most of the students treat her like shit, if they even notice her presence at all.

Through these three characters, Payne gives us all a rich, thoughtful, and often uproariously funny treatise on empathy and perspective, shining an all too rare light on those who aren’t all sugar plums and carols come the Christmas season. Hunham represents a lifetime of regret and bitterness, having been beaten down by an unfair system despite his best efforts. Mary emphasizes the importance of family and personal connections because of what she’s had, cherished, and eventually lost. Tully is a statement of potential, an opportunity to find the good while acknowledging the bad, and respecting everything in between. It’s a fantastic dynamic that Payne gives us.

What follows from this point is an endearing low-key farce — mostly via battles of wills between Hunham and Tully — that pushes boundaries while reinforcing the sentiments that truly matter. For example, the trio is invited to a Christmas Eve party hosted by a member of the staff (Carrie Preston) that lays out each of our leads’ flaws while also showing the value in their angst. Mary gets drunk and loudly mourns her lost son, proving that the strongest of us still need support from time to time. Hunham learns a very hard lesson that many lonely men (myself included) have experienced, that when you get so little attention from the opposite sex, even the most basic level of courtesy and friendliness can be misconstrued as attraction. Tully fingerpaints and flirts with a girl named Elise (Darby Lee-Stack), letting him see the beauty in the most simple of pleasures, before he’s jolted back to reality, forcing Mary to chastise Hunham for his acerbic attitude towards someone who’s just as alone as he is, but without the years of wisdom to cope with it.

The interplay between all three characters is stupendous, but the highlights are the fights between Hunham and Tully, because as Hunham eventually realizes, the two are essentially the same person at different stages of life. They’re cynical, headstrong, convinced of their rightness in certain matters, and willing to compromise for the sake of others despite putting up a personal wall of absolutism and integrity. One of the major lines of the film (also featured in the trailer) is a moment of empathetic truth from Hunham to Tully that sums up their relationship perfectly. “I find the world a bitter, complicated place, and it seems to feel the same way about me. I think you and I have this in common.” It’s fascinating to watch them debate and trade insults, but it’s even more so when they’re emotionally and intellectually honest with each other, even if that means outright lying to everyone else. The involuntary rapport they develop is both hilarious and heartwarming, whether it’s Hunham chasing Tully through the empty halls of Barton, or Tully encouraging Hunham to accept the propositions of a Boston hooker, leading to a likely inappropriate but still gut-busting discussion of sex between a middle-aged teacher and his teenage student.

It all comes back to this central idea that’s as old as culture itself, that history is bound to repeat itself if we don’t learn from it. Throughout the film Hunham peppers in references to the Romans and other ancient civilizations as an extension of his academic expertise. It’s one thing to hammer in names and dates, but it’s quite another to demonstrate how history informs our present, as well as our future if we don’t take it in. The idea hits its literal zenith during a stop at a museum where Hunham shows Tully antiquities that reflect the same issues they deal with in the 1970s, but the metaphorical application is felt throughout. Elites will continue to exploit their privilege at the expense of others unless the exploited rise up to stop it. The most well-meaning of us will still suffer needlessly through no fault of their own. Sacrifice for the greater good is always more noble than asserting selfish priority.

The film has a few small issues here and there, mostly on the periphery. Payne formatted it to feel like it was not only set in the 1970s, but produced in that same timeframe. There are some fun touches in this regard, including using period-appropriate fonts and studio logos, as well as a clever joke where the onscreen copyright date is actually 1971 in Roman numerals. But to the lay viewer, that’s as far as the presentation will get across. Most won’t understand the more nuanced stylistic choices that evoke the New Hollywood era, and once the opening credits are done, the only real connective tissue to the 70s will be the wardrobes and catalog soundtrack. It’s still effective, but a bit too high-minded for the average audience, and most of the plot points could easily be transplanted to the modern day with few edits (say, the fact that students back then would actually have to read textbooks rather than writing essays with AI and Wikipedia). Again, I think that’s kind of the point, that a film set more than 50 years ago (and designed to look like it came out then) is still quite timely today (aligning with the repeating history theme), but it’s not as forward-facing as I think it needed to be to really get the idea across.

On the more nitpicky side, there are a couple of flaws that I think could have been rectified to make things that much more smooth. While the trio of Hunham, Tully, and Mary are about as perfect as it gets, I was a little disappointed that the other four Holdovers (including an intransigent rich boy snot-nosed pissant played by Brady Hepner) are barely in the film. We get just enough exposition and time with them to get to know them as characters, and then they’re deus ex machina-ed out of the picture, giving us no real resolution other than one quick sight gag in the closing scenes. There’s also this fun convention of noting each day of the winter break as the first act progresses, but once the other four are gone, it’s abandoned save for one very late reference. Either commit to the bit or don’t do it at all, otherwise you’re just reminding us that something’s missing.

Normally, this would be where I also say that the film has a fairly predictable plot, including quite a few genre tropes. They’re definitely there, but this is one of the few cases where the exceptions prove the rule. Yes, every major twist and turn in the story is obvious, but as previously mentioned, that feels intentional. Not only does it harken back to the 70s when such structural devices were still relatively novel, but it serves the overall thesis of repeating patterns. You know where things are going because they’ve happened so many times before, and little has changed socially to expect anything different, so in a way, it’s oddly fitting despite its rote nature. As for the more cliché moments, that’s just sort of Payne’s hallmark. His filmography is littered with works that include trite devices because he’s using the rest of the story to subvert them, and this is no different. Ideas like “the friends we made along the way,” and “no one should be alone at Christmas” have been done to death, but rarely are they treated with the right degree of ironic insight that grants any kind of real meaning to them. Payne makes sure to go beyond the platitudes, and the fact that he does it in such a naturally funny way (including what is likely my favorite piece of dialogue of the year) only makes it that much more accessible.

That’s the sort of thing that makes a film like The Holdovers essential, both as Christmas movie and just a piece of pure artistic entertainment that can be watched whenever you like. This is, at its core, a character-driven story about people at various crossroads in their lives, dealing with solitude in their own ways, and seeking companionship in defiance of more saccharine conventions, which is as close to alchemy for jaded assholes like me as you can get, warming the proverbial cockles while still stimulating the critical sectors of our brains. Yes, there are special times and a certain magic to the holiday season, which even I find irresistible once in a while, but it’s crucial to remember that Christmas is also just another day that we all have to live through, and it’s a lot harder for some than for others. To ignore it all is to delude oneself. You don’t have to wallow in self-pity, but it doesn’t hurt to extend an empathetic hand, do something to improve someone else’s life, and take a little time to learn from the past in order to make a better future. I mean, isn’t that the whole point of Christmas?

Grade: A-

Join the conversation in the comments below! What film should I review next? What are your favorite modern Christmas movies? Have you read Marcus Aurelius’ “Meditations,” and if so, is it worth picking up? Let me know! And remember, you can follow me on Twitter (fuck “X”) and YouTube for even more content!

Originally published at http://actuallypaid.com on November 12, 2023.

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William J Hammon

All content is from the blog, “I Actually Paid to See This,” available at actuallypaid.com