The Making of ‘The Holdovers’: “Depressing Sh** Can Still Feel Cozy”

Since The Holdovers hit theaters, the word “cozy” has been at the center of a (good-natured) debate. Viewers and critics looked to the word as a descriptor for its setting (a prep school’s campus during Christmastime), its star (Paul Giamatti, spectacled, mustachioed and sporting corduroys and knits), its period (a nostalgia-clad 1970). Director Alexander Payne, quite vocally, doesn’t agree — there’s a lighthearted, almost saccharine connotation to the term that, understandably, grates on him. The Holdovers, despite its more festive elements, is a cerebral movie about three lost souls (an isolated professor, a recently bereaved mother, a hapless and left-behind student) enduring the loneliest winter break of their lives.  

But it wouldn’t be awards season without a few semantics. Giamatti, for his part, takes no umbrage with coziness. “I know Alexander and I think he’s being a bit curmudgeonly in that reaction because depressing shit can still feel cozy,” he says with a laugh. “I think what is cozy about this movie is how assured the audience feels that you’re in good hands with him as a director.” 

When you learn a bit more about how The Holdovers came to be, the word that comes to mind first and foremost is “patience.” Even more than the average Hollywood endeavor, this production was a waiting game: waiting for the right time to reunite Payne and Giamatti after 2004’s Sideways, for the perfect script, for the perfect filming conditions, for the perfect release date. 

“You know what Tom Petty said, right?” asks David Hemingson with a laugh. Six years ago, the writer completed work on an autobiographical pilot script inspired by the years he spent at a prep school in Hartford, Connecticut — his parents were divorced, and his estranged father was a teacher at the school. “I sent it to my agent, who has the best taste and the worst bedside manner. He told me it was a beautiful but useless piece of writing,” says Hemingson. “He said, ‘It’s so specific that I have no idea what we’re going to do with it.’ ” Then, he waited (the hardest part). At the same time, Payne was looking for his next project. He’d long had the idea of a boarding school-based film on his list of movies to get to one day, always putting it off because of what he describes as a lack of discipline — he hadn’t gotten around to actually researching the thing. A mutual friend sent the director Hemingson’s pilot script, and, Payne tells THR, “a little light bulb went off in my head.” He called Hemingson without any warning, catching the writer as he drove back from LAX after a long flight home from Prague. “I thought it was a prank call at first until I saw the Omaha area code and realized it actually was Alexander Payne,” he says. “And he said, ‘I have this film I want to do about this odiferous, socially challenged professor stuck at school over Christmas — would you be interested in writing it?’ ”

That stinky professor (they gave him the genetic condition trimethylaminuria, which basically means you start to smell like fish as the day goes on), Paul Hunham, was always going to be Paul Giamatti. Payne believes him to be one of our greatest, and most singular, actors and has been thinking about starring vehicles for him since they made that wine-soaked dark comedy 20 years ago. “Listen, I had even conceived of Downsizing for Paul, but when you’re approaching studios and financiers and say, ‘I want the lead to be Paul Giamatti and I want $65 million,’ it’s a no,” says the helmer. “He’s an incredible actor and a big movie star, but he has no comps. There’s no one like him.” This time around, they tailor-made the script for a Giamatti lead. Hemingson wrote the professor’s outbursts (like the meal scene in which he throws a fork down and yells at the students, “For most people, life is like a henhouse ladder — shitty and short — and maybe someday you entitled degenerates will realize that”) and scene direction (like his calisthenics routine or the way he throws a football) knowing the specific blend of dry comedy, self-deprecation and capacity for pathos that the actor would bring. 

Giamatti, who wasn’t bothered by the Downsizing slight (“I understood completely — if you can’t get me, you get Matt Damon,” he says with a laugh), was on board before he even read the script. “I would do anything the guy wants me to do,” he says of Payne. “But once I did read it, I could really feel this character — in a way that was exciting. I know guys like this, they always have a shtick. This guy’s really settled into his shtick.” Giamatti went to prep school himself, and his late father worked in education, eventually becoming president of Yale, including during the years when Hemingson was a student at the university (they met once, during a graduation event). 

The character of Angus, the student forced to hold over at the Barton School under Hunham’s initially resentful watch, was written out of Hemingson’s own emotional truths from his years at school, trying to figure out how to grow up. Payne and casting director Susan Shopmaker, desperate for options after traditional search routes proved fruitless, decided to reach out to the drama departments of real boarding schools to ask about prospects for the film’s secondary lead. Dominic Sessa was a student at Deerfield Academy, an ice hockey player who stumbled into the drama department after a broken femur forced him to pick up another extracurricular. He heard a production company was coming to campus looking for actors, and he thought the audition could be a good way to see what the process was like. “I figured if things went really well, maybe I could be a background extra or something,” he says. “I didn’t know they were looking for a lead, and I definitely didn’t know the movie was for Alexander Payne.” 

Payne felt immediately that Sessa had talent and a “good face for a movie” but wanted to see how the teenager could progress with a bit of coaching, so the team put him through a half-dozen rounds of auditions and a Zoom reading session with Giamatti. “I don’t do what they call chemistry reads, and this was the only time I’ve ever had actors read together ahead of time,” says Payne. “But it became clear that Dominic was the choice.” 

The final addition to The Holdovers’ holy trinity, Mary Lamb, was born out of conversations between Hemingson and Payne about the logistics of Christmas break. “I just asked David, ‘Who cooks for the boys who are holding over?’ and then it became, ‘OK, why is she staying and how can she bring drama and poignancy and join the other two as someone who is broken and in need of a makeshift family?’ ” explains Payne. The two had already decided that the film would take place during 1970 specifically, and while Hemingson was only 6 years old at that time, he remembered knowing a lot of people who had uncles or older brothers who were sent to Vietnam, and recalled noticing that Black men and boys were often disproportionately represented in that group. He wanted to reflect that tragic reality of the era, so Mary was written as not just the school’s cook, but a mother grieving the loss of her son, a former Barton student recently killed in war. 

“The emotional reality of Mary is actually based on my own mother, who raised me on her own,” says Hemingson. “It was a thought experiment about, ‘What would she have done if she’d ever lost me?’ I wanted to make sure that immense, awe-inspiring sacrifice that she made appeared in the film.” 

Da’Vine Joy Randolph didn’t know any of that when she won the role. Hemingson, also a producer on the film, didn’t want to cloud her interpretation of the character. The actress, who first caught Payne’s eye with her stunning turn in Dolemite Is My Name, only learned about Mary’s genesis during the movie’s press cycle. “I’ve loved getting to hear all of these stories, to hear people’s creative secrets being revealed,” she says. “It makes me so happy to know that about her because I set out to embody the full presence of a maternal figure. She’s the only female character, so there was a strong sense of, ‘Oh, I’ve got to hold down the feminine energy for this movie.’ ” 

The expansion of Mary’s character was a major emphasis of the development process, and producer Mark Johnson, who first worked with Payne on Downsizing, was initially impatient with the director’s penchant for fine-tuning every element, describing a helmer always asking for time for one more pass. “But Mary became the heart of the story in many ways,” he says. “And I now consider this to be Alexander’s most emotional movie.” 

Mary, Paul and Angus are holding over at the fictional Barton Academy, a campus that is woodsy, starkly 19th century and vaguely Episcopalian — cozy enough to make it feel Christmas-y but cold enough (in every sense of the word) to make it clear no one actually wants to spend Christmas there. As soon as production designer Ryan Warren Smith read the script, he knew the place was a unicorn. A location scouting trip — during the height of the COVID pandemic — confirmed his initial suspicion that they would need to cobble together a handful of different real schools to make one Barton, but he was taken aback by the filmmaking team’s willingness to be flexible. A targeted three school locations turned into five without any pushback. An interior landscape completely dominated by dark wood, despite Payne’s desire not to have a stereotypically brown color palette, was offset with maroons, mustards and navy blue. On one of their trips, Smith visited a retro bowling alley — “It was even owned by two guys named Tom and Jerry; you can’t make this stuff up,” he recalls with a laugh — that felt perfect for the film. The script didn’t call for a bowling alley, but there was a winter carnival scene that he was worried about creating. “We got Dave [Hemingson] on the phone and said, ‘We found this rad bowling alley, can you rewrite it?’ And we woke up the next morning to a new scene in our inbox,” says Smith. “So many directors want to manage every tiny detail, but on Alexander’s movies, he wants the real world to change what we’re making. He wants to stumble upon something beautiful and allow it to make the film better.” 

Once everyone arrived on set in Massachusetts, time became both a beautiful luxury and something that no one took for granted. In an effort to capitalize on the Northeast’s snowy season, Payne was hoping to start principal photography in December 2021, but Billions didn’t release Giamatti until the beginning of the month, and he needed time to recuperate — and to grow his mustache out. Everyone arrived in January, and Randolph says she immediately noticed the careful, almost indulgent pace. “Let’s say there’s a scene that calls for Mary to do a puzzle, or Mary and Paul to sit and watch TV together — there would be three pages of scenery description in the script,” she says. “Sometimes we took half a day to shoot a single scene. When Paul and I watch TV in the movie, it felt like we were watching a show on set in real time. God bless those editors for watching hours of footage of me in a room just to find the perfect moment to illustrate it.” (Giamatti, for his part, remembers the Newlywed Game scene as an early indicator that the cast had something “really good” together). 

Payne and Johnson made The Holdovers without a distributor, so after the picture was locked — another long, particular and occasionally painstaking process that Johnson says was marked by Payne’s habit of “never being quite done” with a film — they needed to find a buyer. Miramax CEO Bill Block, also a producer on the project, suggested they take advantage of all the executives shopping around at the 2022 Toronto Film Festival. The Holdovers wasn’t on the lineup, but they flew to Canada and held a screening — Focus Features bought the film for $30 million, the largest deal ever made at the festival for a project not officially on the roster. “I was really hoping whoever picked it up would rush and get it out that Christmas, but Focus wisely said, ‘We want to do it right and put together a good campaign,’ ” says Johnson. “So we had to wait another year. When I think about this film, what I mostly think about is patience.” 

The release date of Oct. 29 landed, perilously, two weeks before the end of the actors strike, but everyone involved says that they wouldn’t change a thing. “Something I’ve learned through this process is that something that’s worth doing is worth waiting for,” says Randolph. “That investment will always have an exponential return.”

And Hemingson did what he set out to all those years ago. 

“I lost my mom fairly young, and it crushed me, and I do wish she had been able to see this movie,” he says. “But in the end, I just wanted to tell a story about love.” 

This story first appeared in a January standalone issue of The Hollywood Reporter magazine. Click here to subscribe.