The Big Picture

The Holdovers is a Best Original Screenplay nominee with a script that feels like an old friend—humorous, heartfelt, and welcoming. The screenwriter, David Hemingson, drew personal inspiration for characters like Paul and Mary from his own family and experiences. Difficult scenes, like Mary opening the box of her late son’s childhood items, were carefully crafted to create the right emotional impact.

The Holdovers is having a very good awards season so far. The film debuted in late October to critical acclaim and just in time to garner the heartfelt adoration of audiences who found themselves treated to an unexpected Christmas movie — right in time for the holidays. Set in New England at a boys’ boarding school in the 1970s, The Holdovers focuses on a group of “holdovers” — students with nowhere to go over the holidays, and the staff left behind to ensure that nothing untoward happens to them. A series of unfortunate events leads Paul Hunham (Paul Giamatti), the school’s curmudgeonly Classics teacher, to be the sole member of the faculty left behind to care for the students, alongside the school’s grieving cook, Mary Lamb (Da’Vine Joy Randolph). Among those boys is Angus Tully (Dominic Sessa), a wicked-smart, but trouble-prone junior who has been left behind while his mother enjoys her honeymoon with her not-so-new husband.

Alexander Payne perfectly captures the oddly familiar aesthetics of the 1970s with his precise direction, but it’s the film’s script penned by David Hemingson that feels like an old friend that has returned for the holidays, bringing with it a healthy dose of humor, lessons, and heart. When the Academy Awards were announced this week, The Holdovers secured five nominations, including the coveted Best Picture nomination, Best Actor for Giamatti, Best Supporting Actress for Randolph, Best Film Editing, and last — but certainly not least — Best Original Screenplay for Hemingson. On the heels of his first-time nomination, Collider caught up with the screenwriter to discuss his win and the influences he incorporated into the brilliant screenplay.

The Holdovers A cranky history teacher at a remote prep school is forced to remain on campus over the holidays with a troubled student who has no place to go. Release Date November 10, 2023 Director Alexander Payne Runtime 133 minutes Main Genre Comedy Writers David Hemingson Production Company Miramax, CAA Media Finance

How ‘The Holdovers’ Became a Best Original Screenplay Nominee
Hemingson spent the afternoon following the Academy Award nominations with friends at John O’Groats in downtown Los Angeles. He joked that he was “elated, caffeinated, [and] slightly drunk” in the wake of his achievement, and riding a well-deserved “coffee-Prosecco buzz” that every Oscar nominee should be reveling in. After revealing that I first watched The Holdovers at a film festival held in a quaint theater at a 100-year-old day school in the country — which served as the perfect atmosphere for the film — Hemingson discussed his first-hand experience with schools like Barton Academy:

“It’s kind of a memory play in some respects. I went to Watkinson School in Hartford, [Connecticut], which was a day school, but I spent a lot of time — because I ran cross country and debated — at boarding schools to compete. I had a lot of friends at boarding school, so the whole school culture is something I grew up in because my dad taught there too. It’s been extraordinary to have this sort of memory play come to life the way it has.”

But the boarding school experience is not the end of Hemingson’s personal connections to the film, and it means a lot to him that audiences have resonated with a story that is so deeply personal to him. “I think the most monumental thing for me has been the opportunity to reflect upon my uncle who raised me,” he shared. “He was very much who the Paul [Hunham] character is based on, and to some degree my dad. My mother is sort of the emotional epicenter of Mary. I was recalling my formative years and the most important people in the most important places to me.”

While Paul and Mary were influenced by the incredible adults in his life, they were not the only people that Hemingson drew inspiration from. He looked inward, just as much as he looked outward for personality traits and deep-seated worries. Angus’ backstory, in particular, was influenced by his own parent’s divorce, and — as he describes it — the “burden of uncertainty”:

“I think that arriving at Angus’s dad was me going, thinking to myself, “What was I afraid of growing up? What was the thing I feared the most?” My parents’ marriage collapsed very acrimoniously. I can’t blame either of them, but it was just a really tragic and fraught time for my mom. I always would look back and go like, “What happened to that relationship? Am I capable of having a relationship because of this legacy that I had?” I felt like, with Angus, this anguish that my parents carried and eventually transcended, but I was always kind of afraid that there would be something wrong with me or something wrong in me that would prevent that, and I thought “Okay, well if this kid has that same sort of burden of uncertainty. Is there some sort of legacy that he’s trying to avoid or deny, or he’s terrified to look at?” The idea of a father with mental illness — or someone who had this disruption in their life — and wondering if that’s hard-wired into you. That seemed to be the most powerful thing and [it] echoed my own experience. That’s how I arrived at it. It wasn’t directly my own experience, but it kind of echoed portions of it. I wanted to touch upon that feeling of uncertainty, and alienation, and almost like potential self-loathing.”

Nestled within the feel-good attributes of The Holdovers is something even more poignant and that is the sense of overcoming obstacles, for better or for worse, and that plays into how Hemingson arrived at Angus’ father’s backstory:

“I think for me, I knew that this was going to be a story of revelations, a story of connection. I knew that I wanted to go as deep as I possibly could into these characters. For me, it was always kind of immediately apparent — because my dad ran away from home when he was in 10th grade and joined the Merchant Marine in World War II when he was 15. I knew that, and he never finished high school, but he ended up at Yale on the GI Bill without a high school diploma, with a 10th-grade education. When it came to Paul, I always knew that there would be some sort of disruption in his life that would have stopped him from achieving a goal and [something that got] in the way of his own revelation.”

The Three ‘Holdovers’ Scenes That Make Audiences Cry Were the Hardest to Get Right

Sometimes, it can take ages to turn an idea into a feature-length screenplay, but in Hemingson’s case, “the first 30 pages broke really fast, like really fast. I felt like I was just sort of in a place, and it was very organic. Then it took longer for the rest of it because I would send drafts to Alexander [Payne] and he would comment, and I would rewrite.” And there were two scenes in particular that posed the most difficulty for the scribe, but the challenge paid off because they are key scenes that have made audiences emote the most.

During the interview, Hemingson revealed that he labored over how to pen the scene where Mary opens the box that contains items from her late son’s childhood. He explained that because it was “a wordless scene,” he felt “a responsibility to get that right” because “it’s very much the core of that character — the core of Mary — is my mom, who loved me very deeply. I lost her tragically 25 years ago, and I kind of did this thought experiment when I was writing the character. I was like, ‘What if it was flipped? What if she’d lost me, and it wasn’t the other way around?’ I wanted to reflect on my mother’s strength and her remarkable courage. She was just an incredible person when I was growing up.” He went on to share that he left room in the script for Da’Vine Joy Randolph to bring her own experiences to the role:

“I also knew that I wanted to save the space because of Mary’s actual experience as a Black woman having lost her son in Vietnam. Although I did a lot of historical research into it, it wasn’t my experience. So it was about leaving the space for the actor to take over and tell the true story [and] build upon what I had established. I wrote a lot of dialogue for it and then after a month of going back and forth about how [to] adequately express this, I realized that it had to be just Mary and a wordless expression of the enormity of her grief and transcendence in that moment. Basically, it was getting out of my own way. It was just surreal to be able to see her do that and it was so hard to sort of get to the point where I felt like I was doing that moment justice, and she ended up just crushing it.”

Is ‘The Holdovers’ a Christmas Movie?
Image via Focus Features

With The Holdovers arriving in theaters just in time for the first wave of holidays in November and then arriving on streaming just in time for New Year’s festivities, audiences found themselves drawn to the notion of the film being a “holiday film.” It’s an argument made stronger by the fact that The Holdovers is set during that liminal period between Christmas and New Year’s, where many students at boarding schools have found themselves being “holdovers” for the holidays. While the entire film hinges on many of the emotions that are conjured up during the holiday season, when asked if the film is a Christmas movie — and to stem the debates that will crop up ever after — Hemingson was quick to offer up a “no.” But his answer is a little less definitive than that. Going into his rationale for his answer, he shared that it’s more of a “yes and no” situation:

“Yes and no. It’s absolutely set at Christmas. I like to see this [as] this love story set between three broken people who find each other in the season of miracles. I think Christmas does lend itself to these revelations, and because it’s such an emotionally charged. On the flip side, it’s such a lonely time. I look at it as a dramedy about these three broken people who find and heal each other, and it happens at Christmas. I think Christmas is an important part of it, but I wouldn’t say Christmas is a subsidiary of the story, or the drama, or the comedy. But I would say that it’s definitely the thing that undergirds their relationship and their movement toward forming this family. So it is a Christmas movie, but I think it’s about more than that.”

And if you, like myself, are keen to call it a Christmas movie even after Hemingson’s excellent answer, he’s not going to hold it against you. “Anybody who reflects upon the movie positively, I’m never going to be the guy who’s like, ‘No, it’s not that!’ If you see it as a Christmas movie, and you love it as a Christmas movie, then God bless you. I support and endorse that.”

No, ‘The Holdovers’ Didn’t Actually Start Out as a Pilot

There is a bit of a misconception circulating about the inception of The Holdovers, which seems to suggest that the film started as a concept for a pilot set at a boarding school, but that isn’t the case. While it is true that Hemingson had a pilot called Stonehaven, that script was nothing like The Holdovers.

“I wrote a pilot called Stonehaven, which was about me going to this prep school. It was sort of like, imagine if Max Fisher from Rushmore — because that was me, this very bookish kid who ran toward this sort of romance of prep schools when I was a kid — showed up at the high school from Dazed and Confused. So that Stonehaven. That was the pilot. It wasn’t a pilot that was reworked, it was a pilot that Alexander read and was like, “Oh, you can write about prep schools. You can write about family dynamics. You can write about teenage angst. Could you take this kind of prep school knowledge you have and do a completely different story, but set in the same world?” So aside from some of the emotional dynamics among the characters, the characters in the pilot and the story are completely and utterly different from the movie.”

While Stonehaven wasn’t a true proof-of-concept for The Holdovers, it did prove to Payne that Hemingson “could write in this world.” He went on to explain that “it would have been a lot easier to write the movie if I’d been able to mine the pilot for the story. But what I had was this emotional dynamic between family members that I took that feeling and put it into the movie. So, I didn’t kind of rework the pilot. I just did something original, separate, and apart from it. What I did do was go into my heart and try to find that love and that pain that was running through my life at the time and was commemorated in the pilot. I took some of those same feelings and put those feelings into the movie.”

This question drew another observation from Hemingson about why a story like Stonehaven and The Holdovers appeals to audiences. “I think the coming-of-age story never gets old. I think that people who are vulnerable and fish out of water and people trying to connect, all that stuff, I think people respond to it because I think it’s universal. I just wanted to touch people and put out a positive message of love and understanding. If that doesn’t sound too cheesy.”

How Marcus Aurelius’ ‘Meditations’ Became a Touchstone for Paul Hunham

As the interview wound down, I couldn’t resist telling Hemingson how among all the characters in The Holdovers, I related the most to Paul. With a background steeped in history and anthropology, I know my fair share of stoicism and Marcus Aurelius’ writings in Meditations, which is a major part of Paul Hunham’s character. After revealing how I have a copy of the book on my bookshelf, Hemingson gleefully shared that they had hardback copies made for the film and that he was holding it during the interview. Like so much of The Holdovers, Hemingson has a deeply personal connection to stoicism, and it all leads back to his inspiration for Paul:

“I was fed this as a boy by Earl Cahail, who raised me. [He] is basically the prototype, the foundation of Paul Hunnam. He was a World War II vet who never finished college. We went to Whitman Business College. He was born in 1920. He was married to my mother’s sister, my Aunt Anne. When my parents’ marriage collapsed, he kind of stepped in and was my father figure. He fed me a lot of that stoic philosophy as a boy. That stoic philosophy, that idea of a personal code and an attempt at nobility, is something he embodied and definitely fed to me.”

It doesn’t seem like Meditations has been the word on every interviewer’s lips this award season, as Hemingson seems genuinely surprised and excited to discuss the literary influences that were brought to The Holdovers. “Weirdly enough, and I haven’t really talked about this a whole lot, but there are books that he gave me when I was a kid,” he enthuses. “Books by Thomas Hughes, which were these prep school novels, Tom Brown at Rugby, Tom Brown at Oxford, and Tom Brown: School Days. They were written, I think in the 1880s. And because he was born in 1920 and born on an island off the coast of Washington state, he didn’t really hear a radio broadcast until 1929, so he was 9 years old. So he kind of saturated himself in Hughes and [Charles] Dickens and [William] Thackeray. So for me, as much as it was Marcus Aurelius, it was these sort of precepts of honor and, to some degree, Horatio Alger. But [I was raised on] these strange 19th-century books. A lot of Dickens too. [They] work their way into the themes and the characters.”

But it’s not just his uncle who introduced him to Marcus Aurelius: Hemingson adds that his father was an English teacher and he, himself, was a dual History and English major in college. “I’ve been fed Aurelius, as well as the other books, and this bouillabaisse philosophy. Certainly, Marcus Aurelius was chief among them, but there was other stuff percolating in there as well.”

The Holdovers is now available to stream on Peacock in the U.S.

Stream on Peacock