The Holdovers

The Best Boarding School Winter Break Movie Ever

“This is your Rubicon. Do not cross the Rubicon.”

Happy New Year!

At the end of 2024, I was on a nice run of specifically timed Pitches. The Holdovers ends that run. And while I’m certainly open to the argument that the best time to read about this movie is right before the holidays—open enough that I’ll re-post this some time in December 2025—I’m also of the mind that there’s never a bad time to think about this movie.

It’s a holiday movie, for sure, but it’s also about a heck of a lot more than the holidays. And before we begin, I should suggest to those of you who haven’t seen it yet: see it first, and then come back and read this. I don’t know how many of you that advice applies to, but I’ll say that everyone I know who’s seen The Holdovers loves it.

[Editor’s note: while I’m here and on the topic of specifically timed Pitches, the reports about Meta’s changes in January 2025, and the inauguration guest list, have made the Pitch for The Social Network especially relevant again. Check it out, especially if you haven’t before.]

I, of course, really dig this movie. It grows on you, both while you’re watching it and from one viewing to the next. As I write, I think The Holdovers would fit well in the current “Making, Breaking, and Bending the Rules” unit. After all, at its core, the subject matter isn’t unfamiliar: the story’s inclusion of a coming-of-age arc, a reluctant loner thrust into the position of parental figure, holiday-related drama, race dynamics, and social commentary certainly gives us moments we feel like we’ve seen before, and makes us think we can guess what’s coming next.

Very often, of course, these guesses end up wrong.

I’ve thought a lot about why, and what my consistent guess-wrongness says about the movie. And what I’ve come to is that what stands out over and over again in The Holdovers (and makes it so Film Lit-worthy) is its confidence. When it has the opportunity to go big, it often pulls back, and goes small. It doesn’t hit you over the head with or congratulate itself for its social critiques. (I wish I could give credit to the original take-giver who said on Instagram, “It shows you how to tell a story that is emotional but not sentimental.” I had saved the post, but have lost it.) And it has enough confidence in the story—and, importantly, in the viewer—to be patient with its turns, key exposition, and reversals.

“Yeah, well, friends are overrated.”

We see The Holdovers’ confidence first in the way it is not afraid to lean into its characters’ struggles. They don’t get what they want, even and especially when the viewer wants them to. As I was watching the film for the second time, I found myself identifying (and almost counting) the moments that would have gone differently in the hands of either an AI or a Hallmark screenwriter. And the delta between who these characters are and who they could have been (and have been in other stories) gives these characters nuances that are by turns refreshing and confounding.

Take, for example, Mary. I’m on record saying that Da’Vine Joy Randolph deserved to win Best Supporting Actress for her portrayal of Mary, so I was very happy when she won. (And, yes, I’m happy that my prediction that Emily Blunt would win was incorrect.) She executes a high degree-of-difficulty task very well, and thus epitomizes what the whole enterprise does well.

And we can imagine easily what Mary looks like in less-capable hands, right? A poor, Black woman who serves the rich, white students at a prestigious school could lapse easily into an obvious and clumsy caricature vehicle for social, racial, and gender commentary. I’m smiling as I write this: she has all the potential to be a character my beloved Matt Struckmeyer would despise. (Especially if you don’t get what I mean there: one of these days, I’ll write more about Matt and his influence on my film watching and teaching career.)

Instead, Mary emerges as a stock character who resists reductive positions. She’s suffered, for sure; and much of that suffering is unfair and inextricable from her race and financial status. She’s not naive about that. And she’s also not especially bitter or prone to projection or displacement. I love it when Paul tries to connect with her as a fellow class warrior. He says of the Barton students, “They’ve had it easy their whole lives.” And what does Mary say? “You don’t know that.” She’s unwilling the suffer the Barton fools, and she’s just as unwilling to minimize them or their humanity.

I’m also on record saying that I don’t get too worked up about Oscar snubs. And, even if I did, I’m way too late to be asking this question. Nevertheless, here we go: Are we sure that Dominic Sussa wasn’t snubbed for his performance as Angus Tully?

Seriously: he plays one of the most believable teens I can remember.

[Editor’s note: Off the top of my head, I thought Elsie Fisher in Eighth Grade was just about perfect. I’ll also add, even though I’m not sure it’s fair: my gold standard is Sarah Vowell, the voice of Violet in The Incredibles.]

Like Mary, Angus carries a lot around with him. And like Mary, he has an impossible moment that makes my heart leap out for him—a moment of pain I can barely imagine. Hers is when she puts the clothes in the drawer. Angus’ is when he sees his father. He knows why his father is where he is; he’s so afraid of anyone knowing that he’s lied about it until the last possible moment. And he also knows that he’s been diagnosed with Depression. And so when his father spouts his conspiracy theory, it’s heartbreaking, yes; and it’s also terrifying, because Angus doesn’t know that he won’t end up like that. (Bless him for his confession to Paul about this fear.) Just a brutal, brutal scene, played so authentically and wonderfully.

And yet, as sympathetic as he is, the film is confident enough to let him bask in jerkiness every once in a while. Angus is a fake tough guy with shields that are intimidating, but brittle. He does know the difference between right and wrong, but so often his insufficiently developed prefrontal cortex betrays him, and he ends up doing really dumb and hurtful things. He has just as moments when it is easy to feel for him as he has moments when it is easy to want to yell at him.

And then there’s Mr. Hunham, who reveals the film’s confidence in many ways, but most directly through the fact that he is a legitimately bad teacher.

Okay, so let’s do some deck-clearing in the name of fairness. First, his aims are often noble. And, yes, I do think a very (very interesting) Film Lit discussion question would be a classic “Attack or Defend” in his scene with the Headmaster. On the one hand, I think anyone even semi-familiar with the teaching profession can understand Paul rankling at the suggestion that he be more “elastic in [his] assessment” of his students. And I—honestly—would love to hear what students think of the headmaster’s suggestion that Paul could be an “excellent” teacher, but for his “traditional” approach. And I’d love to ask my students plainly, “Should a teacher be aware of politics when they grade students?”

Second, he does show signs of genuine potential. His explanation in the museum that “history is not simply a study of the past,” that it “is an explanation of the present,” is just wonderful. And I’m glad Angus gives him credit.

Third, I do think we’re supposed to believe that his students are legitimately difficult to teach.

And yet, his performance in the classroom suggests that he’s just not a very good educator. Even if we allow for the “time and era” apologist takes about teaching methods that just wouldn’t work today (at least in Palo Alto), he’s still just a jerk. The students aren’t unreasonable in their disdain for him. They are not learning, and—if I may—I don’t think it’s unfair to at least think that his class warrior mindset of resentfulness seeps its way into his disciplinary methods; he enjoys putting these rich kids in their places.

I’ll put it this way: the easy way out would be to present Paul as a curmudgeonly but excellent educator whom we begrudgingly admire because he, as my guy Nick Carraway would say, sees “himself standing alone on the last barrier of civilization.” It’d be easy to invite the viewer to think that if Paul ever opens himself up and learns to loosen up, he will achieve self-actualization as a teacher. Instead—and I remember smiling as I realized this point—the viewer sees his teaching performance and has open and fair reasons to think that after all these years, he still doesn’t know what he’s doing.

“He’s not entitled to my story.”

The Holdovers also brilliantly shows its confidence in the way it slow-plays its story. It has the confidence to hold its storytelling cards close to its vest—and thus give us a story that is patient at first, and then relentless. As a result, the early sense of the familiar and mundane lulls us into an ultimately incorrect sense of where the film is going.

This storytelling confidence has two direct consequences. The first is that the characters come off as authentic. As even Fred Rogers says in Beautiful Day in the Neighborhood, “There is no human life without pain.” The Holdovers’ characters are dealing with their own traumas, for sure; and they live with them the way most of us do: by bottling them all up inside until we just can’t anymore.

If and when you watch The Holdovers a second time—and yeah, you should—the characters do give you a few tells as to the causal links between their pain and their behaviors. Even then, though, the tells are sparse and subtle. The first time you come across the story, you have no idea the lies these people are living through.

And that leads us to the second consequence of this film’s storytelling confidence: the last twenty minutes are relentless, just one devastating secret or reversal after another. The initially familiar storyline turns acutely painful quickly. I mean, it’s just one gut punch after another, and each one hits spots that are sore and raw for both the characters and the viewer.

“I just told the truth . . . mostly.”

That includes the ending, another moment when the story—smartly—goes small instead of big. The farewell between Paul and Angus is not exceptionally sentimental. I mean, they don’t share a hug; they shake hands firmly. And then—I just love this—Angus blithely jogs away.

It’s not clear to me that either Paul or Angus knows how sad this ending is. Let’s start here: what are the odds they’ll ever see each other, or even hear from the other, again? This is the 70’s! They’re not going to connect on LinkedIn or Facebook. It’s a wrap.

Moreover, the ending openly invites us to ask a classic Film Lit question: What happens to Paul in the months and years after the movie? I, for one, am worried about him. His odds of getting another teaching job are exceedingly slim. (Another fun Film Lit question: Assume he does apply for another teaching job. Does he tell the truth—the whole truth—about his educational and career background?)

And I’m sorry: I am pessimistic about the potential success of his theoretical monograph. First, I have to say: I love love love that his goal is to write a monograph. As he admits, he’s not sure he’s “got a whole” book in him. (I also love Mary’s response: “You can’t even dream a whole dream, can you?”) So, even as modest a goal as it is, will he ever actually sit down and grind through and write it? I wouldn’t bet on that. And, even if he did, who would buy it?

It reminds me of that brutal scene in Little Miss Sunshine when Stan Grossman confirms the death of the “9 Steps” program, and flatly tells Richard, “It’s you, Richard. No one’s heard of you.” Who out and about in the universe is going to dish out money to buy the latest monograph from Paul Dunham?

Sigh. Bless him.

“Keep your head up, all right? You can do this.”

“Yeah, I was gonna tell you the same thing.”

See you next time, when we discuss The Untouchables (1987).