Before The Holdovers, director Alexander Payne and actor Paul Giamatti hadn’t worked together in nearly two decades. After premiering at the Toronto International Film Festival in 2004, their Oscar-winning comedy Sideways went on to garner countless awards and generate profitable spinoffs—a Japanese remake, musical theater adaptation, film-branded bottles of pinot noir. During the 19 years since the film’s release, Payne and Giamatti attempted to team up on new projects, but none came to fruition until a screenplay by David Hemingson arrived on Payne’s desk a few years ago.

Envisioning the script as something that could be revised and expanded upon to incorporate ideas Payne had for a similar project, the director worked with Hemingson to create roles any actor would dream of playing. For the lead, Paul Hunham, a strict, prickly, at times Scrooge-like “work before all else” teacher at a New England boarding school for teenage boys, they wanted Giamatti. With the actor on board, Payne then cast two other key roles: Angus (Dominic Sessa), the troubled student begrudgingly
chaperoned by Hunham for the Christmas break once his mother cancels holiday plans, and Mary (Da’Vine Joy Randolph), the school’s cook, who is mourning the loss of her son in Vietnam. Over the film’s duration, Hunham, Angus and Mary will travel across Massachusetts to see various people and engage in some emotional (and very humorous) experiences.

Early praise for The Holdovers had critics noting that it’s the type of film “they just don’t make anymore,” and while there’s some truth to that claim (the film is set in late 1970 and often lovingly feels like it was made then, too), it’s probably more accurate to observe that it’s the type of film that most studios don’t believe audiences want anymore. In finally getting to work together again, Payne and Giamatti make a compelling case for why that just isn’t true. A few weeks before The Holdovers made its world premiere at the Telluride Film Festival, I spoke with Payne about toggling between comedy and drama, making a ’70s period piece, the film’s keen music choices and much more.

The Holdovers opens on October 27th courtesy of Focus Features.

Filmmaker: Earlier this year at the TCM Classic Film Festival, prior to a screening of George Stevens’s Penny Serenade, you observed that “directors trained in comedy are the ones most adept at drama, most adept at pathos,” citing Stevens, Leo McCarey and Frank Capra as prominent examples. What was it about those directors that made them feel appropriate for this observation? I thought of your quote while watching The Holdovers, a film that feels very much like the work of a comedy director at their most comfortable when depicting a film’s more dramatic moments.

Payne: I appreciate the comparison, and I appreciate your pointing that out. I was really honored to be at that event with Mr. Stevens [George Stevens, Jr., the filmmaker’s son], who’s quite a guy. Regarding that quote, I’ve actually felt that way for years—that some of the directors most adept at delivering unsentimental emotion and pathos are comedy directors, like the ones you mentioned, McCarey and Stevens and Capra. Let’s put [Charles] Chaplin in there as well, and I would even add Yasujirō Ozu, as there’s a way in which you can watch Ozu’s movies as comedies. Ozu has a really rich sense of humor and even made out-and-out comedies in the early days. There was always a lot of humor in his work, but, of course, no one could make audiences cry like Ozu.

A predecessor of his was perhaps Anton Chekhov, who began writing short comic provincial sketches, then slowly but surely eased his way into richer work that had tremendous emotional effect. All the while, he never lost that sense of—and I mean this in the richest way possible—caricature and comedy, in as much as comedy uses caricature in a mature way to laugh at the recognition of truth, of truthful things you’ve seen in your own life or your friends’ lives. I’m always reminded of the story of someone asking Chekhov for feedback on a short story and Chekhov writing back, “Your short story is too sentimental. Keep your story cold, so that the emotional effects stand out in relief.” I think that’s true, especially of the directors I’ve mentioned. I’m sure there are others you could come up with who create a funnier backdrop onto which you can then allow emotional effects to stand out. You can even begin an interplay between the two, where you have a dramatic emotion and then a laugh, and it keeps the movie from descending into drear. Ideally, it lets the tears flow that much more through the laughter. I’ll also add that in ancient Greece the comedy mask and the drama mask were never separated. They were always together, the comedy and the drama.

Filmmaker: How did David Hemingson’s screenplay for The Holdovers originally come your way?

Payne: I had had the idea for the movie for about a decade. What I didn’t have was the discipline to research it, and I certainly didn’t have the life experience, of going to an Eastern prep school, to write about it with any accurate detail. Then, four or five years ago, I was submitted a pilot by David Hemingson set in the world of a prep school. I contacted him and said, “Hey, man. Let me introduce myself. I’ve read your pilot, and while I don’t want to make it, would you consider writing an idea of mine that’s set within the same world?” [laughs]

Filmmaker: And there was a French film from the 1930s that also served as inspiration for this story, is that correct?

Payne: Yes, there had been a film [Marcel Pagnol’s Merlusse] that I had seen at a festival, probably Telluride, that I found to be a pretty good premise for a movie. It wasn’t the story, per se, but the premise, so that’s the premise I shared with David. I thought it would apply very well to an American prep school. He never saw the movie, so he wrote an original screenplay based on a premise I had suggested.

Filmmaker: Had you known David prior to this?

Payne: No, I hadn’t heard of him.

Filmmaker: What was it in his writing that made you think he would be the ideal person to reach out to to share what you had in mind?

Payne: I’d have to go back and reread his pilot, as I don’t recall the details of it, but I do remember the initial impression of it being very good, and that it had good characterizations and showed that he knew the world very well.

Filmmaker: Did your initial idea involve the Angus character? Or did you see your way into the story from the professorial point of view, from the perspective of Paul Hunham?

Payne: The initial premise was a group of boys at a boarding school who had nowhere to go over the Christmas holiday and the very disliked teacher selected that particular year to take care of them. Then, there’s a boy who has to remain at the school at the last minute because his mother wants to go on a honeymoon of some sort. That’s all the story was at the time. There was no cook character, Mary, just that basic premise. 

Filmmaker: It also feels like a classic addition to the “prep school” genre, which my generation may closely associate with films like Martin Brest’s Scent of a Woman and other prep school-adjacent movies, where there’s an adult character (typically a professor) who has to oversee a group of young men in an academic setting, and he goes on to befriend one student in particular. Were there other examples in your viewing history that came to mind?

Payne: Not really, although in the last 30 years or so, you had, yes, Scent of a Woman, and Dead Poets Society and Wonder Boys. I was almost hoping that my film, inasmuch as I was thinking about those movies—which wasn’t very much—would be somewhat of the anti-version of those. I wanted the film to be a period prep school movie, but one that wasn’t baked in rosy colors and fall leaves tumbling down or didn’t feature idealized student situations that ended with them learning nice life lessons. I didn’t want any of that stuff. While it’s not a boarding school movie per se, I thought about Tony Richardson’s film, The Loneliness of the Long Distance Runner, from time to time, which is a British film that’s brutally anti-authoritarian and is much more about juvenile delinquents. I can’t say that it’s an influence on [The Holdovers], but in as much as you bring up prep school/boarding school movies, that’s a good example of one I like.

In as much as we—meaning David, myself and later, by extension, the DP, Eigil Bryld, and the production designer, Ryan Warren Smith—were thinking of other films [as references], we were more inspired by early movies from the 1970s that, for us, had a tone our film could look like a second cousin to. In particular, I’m thinking of Hal Ashby’s The Last Detail and The Landlord.

Filmmaker: Did the period your film is set in affect its presentation? By that, I mean the film embodies the era right from the start, with the MPAA rating designations and vintage studio logos and production credits. The actual image has a very soft focus to it, almost a washed-out quality, like celluloid that’s showing some wear, that modern audiences are much less accustomed to. Was that look and feel of the film influenced by setting it within the period that you did?

Payne: Very much so. I wanted to make a movie not only set in 1970, but that looks and sounds as though it might actually have been made in 1970. I wouldn’t say that the effect is 100 percent like the British [Mark Jenkin film] Bait. That guy was a maniac and really went to town with it! This is not quite as dogmatic as that movie, but it’s certainly on its way—not just in the technical aspects you mention, but also within the filmmaking style and the sense of story, of character, the rhythm of the storytelling, the narrative. In as much as you might mention Hal Ashby or even Bob Rafelson, I wasn’t saying to myself, “Oh, I’m making a Hal Ashby movie here.” No, what I was asking myself was, had I actually been making a movie in the 1970s, what movie would have come out of me? I got to play with that thought experiment a bit. I got to time travel.

Filmmaker: I believe this was your first time working with cinematographer Eigil Bryld.

Payne: Yes, the irritatingly handsome Dane [laughs].

Filmmaker: And this comes after your having worked with Phedon Papamichael on your previous four films, Downsizing, Nebraska, The Descendants, and Sideways. Was the visual look you’re describing for the film something that was easily translatable to a cinematographer whom you hadn’t previously worked with?

Payne: He got what I was going for, and while I wish I could give you a really substantive American Cinematographer–quality answer about it—i.e., “Here’s how we set about to achieve the look of The Holdovers,” [laughs]—Eigil just understood what I was going for. And we can’t really talk about that without also talking about the production designer and, by extension, the costume designer, Wendy Chuck, and hair and makeup. You have to talk about everything photographed, as well as the quality involved in photographing it. Eigil approached his work very seriously and dogmatically, as any good cinematographer would, to give this particular film its own unique look, a look appropriate both to the story and to the director’s aspiration for the story. Of course, this would’ve been hard to achieve without the right locations and the right set dressing, which the production designer, [with whom] I was also working for the first time, was able to achieve.

We didn’t want to be rubbing your nose in it, like, “Look how period accurate this is!” We weren’t making a period film, but rather a contemporary film set in 1970. I think a mistake a lot of period films make is having the mindset of, “Since we’re setting the film in 1958, everything in the film must be from 1958—the furniture, the cars, etc.” But no, they had old shit back then, man! 

Filmmaker: Was that also true of implementing additional elements from popular culture, like Bob Eubanks hosting The Newlywed Game and Guy Lombardo’s New Year’s Eve television special and, late in the film, having two characters attend a screening of Arthur Penn’s latest feature, Little Big Man?

Payne: A little bit. The Newlywed Game inclusion was written into David Hemingson’s script, and it found its way into the dialogue, too, because it makes Paul Giamatti’s character say [to Mary], “Oh, how long were you married for?” and they start talking about their own backgrounds. The Guy Lombardo footage was also in the script, I think, as that’s just what people did back then: turn that program on right at midnight for their New Year’s Eve house parties. Including Little Big Man came to me because we had a scene set in a movie theater, and I thought, “I’ll research what was playing in theaters in December of 1970.” And there was Little Big Man, a picture I loved, seeing it probably four times in the theater when I was nine and 10 years old. So, that inclusion was a bit personal.

Filmmaker: There’s one snowy exterior shot that comes during the opening credits of the film of what is known as The Bridge of Flowers in Shelburne Falls, Massachusetts, that really stuck with me. I can’t exactly determine why, but that shot took on an almost miniature effect for me, as if we were being introduced to this town through a snow globe, an item that, of course, winds up playing a larger role later in the film.

Payne: Oh, I’m going to use that in future interviews, thank you. [laughs] That’s brilliant!

Filmmaker: That bridge and the snow falling, it all feels very much of the time you set the film in! Maybe that’s a New England thing, but there is a lot of age and wear to the locations and buildings and structures in the film, so I wanted to ask about your location scouting.

Payne: First of all, thanks again. I want to steal that [laughs]: “It looks like a snow globe, just like how one plays a large role later on in the movie.” That’s great.

But what your question made me think of is the ease (not that it was easy) with which we were able to make a period film in New England, and specifically in Massachusetts. As it turns out, change comes slowly to Massachusetts, and for almost every location, we had a few choices that were aged, lived-in and very period. An example is the candlepin bowling alley we feature in one scene. Of course, we added some stuff [to the location] to make it exactly appropriate to when the scene takes place, in 1970, but it was like a time warp walking into that bowling alley. It was like you were walking into 1950 and 1960 and 1970 and 1980 and 2022, all at the same time! To this day, it remains unchanged, and we found quite a few places to be like that.

Filmmaker: And you found the fictional Barton Academy by filming in multiple high schools?

Payne: Five different schools, yes. That’s pretty common and is something you always have to do. When I made Nebraska, 10 years ago, the fictitious town of Hawthorne, Nebraska, was fashioned from about seven different small towns in northeastern Nebraska. Similarly, the fictitious Barton Academy in The Holdovers is cobbled together from five different schools, because one might have a good gymnasium, one might have a good cafeteria and another might have a good exterior to use. You have to pick and choose.

Filmmaker: You’ve famously worked with Paul Giamatti before, but I wanted to ask about casting the other two leads who make up your film’s lead trio (Hunham, Angus and Mary). Dominic Sessa was someone you found at Deerfield Academy (one of the schools you used as a stand-in for Barton Academy), is that correct?

Payne: That’s correct. Dominic had never been in front of a camera before, not even in a student film.

Filmmaker: Was that then a pretty fortunate circumstance, of being in the midst of location scouting and finding a way to also use that time for casting?

Payne: Kind of. That also happened with Chris Klein when we were casting Election. I was scouting a high school in Omaha and, completely by accident, Chris Klein came tumbling out of a gymnasium door, and the principal shouted, “Hey, Chris! Come over here and meet, umm, Andrew Payne! He’s a movie producer!” And then, the principal told me, “You should’ve seen Chris Klein [on stage at the high school]. He was wonderful as Tony in West Side Story!” So, I just met this high school kid named Chris Klein and thought, “Wow, look at this kid.” Then, two months later, after not finding anyone I liked in either LA or NY, I called that principal to ask about that kid and wound up casting him.

But in the case of The Holdovers, we—casting director Susan Shopmaker and I—received about 800 submissions from across the English-speaking world for the role of Angus. And while we were able to cast some of the other parts from those submissions, we didn’t cast the lead. So, we finally did something we’d said we’d do, which is call up the drama departments of the schools we were going to shoot in to see if he might be lurking around there. And there he was, at Deerfield! We called the head of the drama department, who told us, “We have a number of students who would be delighted to audition for your little movie,” and there he was, Dominic Sessa. He was already something of a star actor in the drama department, but only on stage. Dominic had never done anything in front of a camera before, and he took to it like a duck to water.

Filmmaker: Did you hold chemistry reads between Angus and Paul to gauge their connection to the material and to each other?

Payne: While I don’t really hold so-called chemistry reads, I did in this case, as [Dominic] was pretty new to film acting. I thought Paul could help him get into the rhythm and feel of the reality of the dialogue before we would be on set, where it feels more real. I wanted to get Dominic out of that antiseptic atmosphere of the casting office or Zoom. I wanted him to read with the actor he would actually play against. I do that with a lot of actors, especially when you have day players or actors without a lot of experience and whom you have to bring back two, three or four times to really see how bulletproof they are. You’ve read pretty well with me or you’ve read pretty well with the casting director—OK, but let’s step it up and pair you with a real actor and see how you do. Throughout everything, Dominic kept jumping through all of these hoops with his eyes closed and laughing. He was great.

Filmmaker: What led you to casting Da’Vine Joy Randolph? She has a few film credits and a strong, Tony-nominated theater background and, I believe, even attended the Yale School of Drama.

Payne: Yes, she received her Masters at Yale, just like Paul. I had asked for Da’Vine by name, and while I wasn’t sure I’d be casting her, I certainly wanted to ask her to audition. I had liked her so much in Craig Brewer’s film, Dolemite Is My Name.

In all of my movies—even the ones that are more on the serious side, like The Descendants—I find myself casting actors in dramatic parts who possess comic chops. Those actors instinctively know how to keep their role from descending into drear. No matter how dramatic or sad your movie is, you still want it to be, in some way, delightful and charming. You want movies,  in general (or at least I do), to be charming to some degree, on some level, and I consistently find that it’s the actors who have comic chops who are able to deliver the goods dramatically without being all boo hoo hoo about it.

Filmmaker: When Hunham and Angus take their road trip to Boston and visit some familiar sights, including ​​Faneuil Hall and the Orpheum Theatre, I was curious as to how conscious you were of choosing what to show in the frame. When shooting exteriors on a period film, the wider your frame is, the more expensive the shot will be due to how much more period-specific things you have to fill it with. How were those choices made, where you thought, “OK, if we pan a little bit more to the left, we’ll need to redress this entirely,” and so on and so on?

Payne: This is Filmmaker Magazine, so I’ll talk about that a little bit [laughs]. You obviously know Boston to some degree. The good thing [about] that location outside of the Orpheum Theatre was that it was [period] accurate and idiosyncratic. The Orpheum Theatre really is located at the end of that street, so when you’re setting up an exterior shot and staging a scene there, you think, “Thank God. I only have to worry about this one enclosed street.” It’s the kind of street you saw in Eyes Wide Shut. [Kubrick] shot that film in England and was recreating New York City on an outdoor set. He purposely picked a street and intersection that were T-shaped. Our excellent property master was not only a good prop man but also a car guy, so a lot of the cars in the shot were his. If he didn’t personally have them, he was able to find the car collectors who did and was able to track down old yellow taxis, too. We just set up a taxi stand [where Angus enters a taxi to leave Hunham at the theater] and dressed the street in period cars and removed a couple of contemporary signs. In the distance, in the back of the shot, there’s a busy one-way street that’s slightly visible, and we digitally put in some vintage cars there. One of the conditions of shooting in downtown Boston is that, “Oh, you can have this, sure, but we can’t stop traffic,” or “you can have this, but you can’t put your own cars there.” 

Filmmaker: The film’s soundtrack and Mark Orton’s score take on their own strong identities that complement the look and feel of the film, and I was curious how you selected certain songs (and created new pieces) to serve as additional “reinforcements” for the story. Earlier, you referenced Hal Ashby, and he’s someone who comes to mind when I think about music choices as well.

Payne: Well, the only thing specifically Ashby-ish that might invite that comparison is the Cat Stevens song, but it wasn’t meant to be a direct homage [to Ashby]. I even tried to resist it because I didn’t want comparison to Harold and Maude. But the song fit so well in that scene, where [Hunham] watches [Angus] ice skate and, for me, it’s the scene where those two characters really fall in love. It felt right, so I went for it.

The music in the film is divided into three or four different categories. One is original score composed specifically for the film by Mark Orton, who had also written the score for Nebraska 10 years ago. I thought his sensibility would be correct for The Holdovers. Then, there was the period music used as score, and that included the Allman Brothers Band and Cat Stevens and the British musician Labi Siffre. [He’s] used twice, once when the boy steals the keys and runs around the school at night, and then again over the end credits as Paul’s character drives away from the school. I’d been working with the same music editor, Richard Ford, for 25 years, since Election, and he found that piece, a real discovery for me.

You also have music which is played by the characters. For example, there’s the music playing on the stereo at the Christmas party, both upstairs and in the room where Mary is, and downstairs where the kids are playing. We also use Christmas music as score, such as the Swingle Singers and the von Trapp family—known for, yes, The Sound of Music. Another example is when they’re in the bar/restaurant getting a burger and run into Miss Crane (Carrie Preston). We had Tony Orlando and Badfinger playing [on the jukebox] there. Each of those choices took a lot of time. You go through many alts for each one and then finally find what works, what you can afford and what you can track down. Sometimes, you pick out music but you can’t track down the musicians and can’t obtain clearance. It was a very long process, but one that we’re proud of—“we” being Richard Ford and Kevin Tent, the editor, and Matt Aberle, the music supervisor, and myself. We were so happy with how the music turned out that we easily convinced the music department at Focus to put out a double-album record of the soundtrack.

Filmmaker: This is your first time working with Paul in close to 20 years. When the casting was announced, you didn’t hide your excitement to be working with the actor again. Had this been a long time coming? Did this script feel custom made for Paul? Was he always the first choice?

Payne: Yes, yes and yes. I wanted to work with him all this time, but I don’t make films every year (I’m a little slower than that), so I just had to keep waiting. I’m glad that this script was ready when it was, and it was written for Paul, and we couldn’t have been giddier to work together again. A few crew people noted that between takes when I’d go over and talk to Paul to give him a suggestion for the next take, I’d only need to use two or three syllables. The shorthand between us is very short.

Filmmaker: How did the experience of your previous feature, Downsizing, compare to making this new film? I know Downsizing was a very large-scale movie….

Payne: A large-scale tanker, yes [laughs].

Filmmaker: But it definitely has a following! There’s a passionate group of cinephiles that really took to the movie.

Payne: If you can ever get me the names of those seven people, I’d be very grateful.

Filmmaker: Nonetheless, after that experience, were you looking to work on a project of a smaller scale, where all the effects are in camera and performance-based?

Payne: Totally. I really did not enjoy working with visual effects. I mean, it’s hard enough shooting people sitting around a table or in a car and trying to make that look interesting without the added layer of, “Hm, is there enough contrast in the artificial clouds we’re adding in?” I wasn’t the happiest director making a big visual effects movie like Downsizing, although I saw the movie again, projected, a few months ago (I hadn’t seen it in years), and I thought the visual effects were actually pretty good, all things considered. But I much prefer making old-fashioned movies, and I’ve basically been trying to make ’70s movies my whole career. The Holdovers is the most full-on of those because it’s actually set in the 1970s and somewhat fashioned to appear it had been made in the 1970s. I just like good old-fashioned filmmaking about human stories.

Filmmaker: You mentioned having a shorthand with Paul, and in working together again after so many years, did you both take note of the added experience you had accumulated [since Sideways]? Did you feel more confident in your abilities this time out?

Payne: I simultaneously feel that I have some experience under my belt, some knowhow and control, and that, geez Louise, each new film still feels like the first one. You certainly have to approach each movie not as though it’s your next film, but as though it’s your first, to put the same degree of enthusiasm and wonder and energy into it as you did when you were a young filmmaker. I think that’s pretty key. You’re always wondering, “What’s a movie? And what is this movie?” As far as technique goes, I’m pretty comfortable, I guess. You still have varying degrees of panic at the beginning of each day on set—“Am I going to figure out how to shoot it efficiently and cleverly and not drive home that night thinking, ‘I missed an opportunity that I can never retrieve again?’” When you’re a very young filmmaker, when you’re in film school, you are in the editing room and your teacher says, “Oh well, that’s fine if you’re stuck there. Just cut to the close-up. You did get a close-up, right?” You go pale and say, “Um, no.” And then on your next film, you get too much coverage and think, “Oh, god, I didn’t need to wear out the actors by getting all of that coverage,” and then, finally, you find a happy medium. I feel pretty comfortable there now.

It was delightful to work with Mr. Giamatti 20 years later, with all of the massive experience he’d accrued under his belt—he’s been on 50 times more film sets than I have in those intervening years. We just get along very well, personally, and understand each other, in that director/actor way. We know how to make the same movie, and that’s always key for the director and their cast, particularly the principal cast. They all must know that they’re making the same movie, and Paul and I instinctively agree about what movie we’re making.