Interview: Alexander Payne on Creating ‘The Holdovers’ and Making It Good til the Last Drop

“Do you want to go outside? It’s a nice day, let’s talk out there.” This was my first bit of direction from Academy Awards nominated writer-director Alexander Payne as I was able to interview him at the 2023 Middleburg Film Festival about his latest film, The Holdovers. As we made our way outside to sit down for our interview, bypassing the original room of the interview, his eye caught something that sparked his interest; a drink stand serving Coke floats for festival attendees. “Coke floats? I haven’t had one of those in a while. I’d love one. Ryan, do you want one too?” Pleasantly surprised by the offer, I said with a smile on my face, “Yeah, that sounds good.” His PR team then proceeded to take the liberty of grabbing our beverages while we found the right place to sit down on a crisp October afternoon at the Salamander Hotel and Spa.

As we began, Payne didn’t want to answer questions about the film at first, but rather turn the interview around and start asking about where I was from and how one gets into the film writing business. In doing this, he set the stage as a regular conversation rather than the types of in-depth interviews he had been doing earlier in the day and all around the festival circuit, as The Holdovers had premiered at the Telluride Film Festival, as well as the Toronto International Film Festival as well. He had also been to “London, Leon, Paris, New York a little bit” before arriving in Middleburg, Virginia, a place where Payne’s films have had a history with the festival before as his film Nebraska was one of the first films to premiere at the very first Middleburg Film Festival. He wasn’t able to attend that year for the screening, so he made sure to join in the festivities this time.

It was at this time that the floats arrived. A serendipitously nostalgic choice of a beverage to have with Payne, as he himself is taking the audience down a familiar lane with his latest venture. From his point of view, The Holdovers is a “continuation” of the ideas and elements in common with my previous films.” Alongside being a comedy set in a high school like his masterpiece Election, Payne stated that the film “has Paul Giamatti from Sideways and the sense of a two-hander. It has an older character and a younger character getting to know each other better through some sort of road trip like in Nebraska.” The idea of The Holdovers came together from an idea that Payne had for a story set in the New England area. He sat on the idea, till he read a script for a pilot episode of a passed on TV series set at a boarding school. Payne thought the script was a “very well-written, contemporary” story he was intrigued by.  “I called up the writer David Hemingson and said, “I’ve just read the screenplay you’ve written, submitted to me through your agents. I don’t want to do it, but would you consider writing a feature script for me based on an idea I’m going to give you?” And he said, “Yes.” So together we hashed out the story, decided the year in which the movie would take place, and then he wrote it.”

From that conversation, The Holdovers was created, a film about an old school, grumpy history teacher at a remote prep school, who is forced to stay on campus over the Christmas holidays with a troubled student whose parents have left him behind for the winter break. In prepping the film, a big part of The Holdovers was finding a school which most of the film would be set in. Payne thought he and his team would “wind up scouring New England to find all the locations” but he “wound up limiting all locations to the state of Massachusetts,” with the film’s fictional Barton Academy “comprised of five different high schools.” Right before he continued, we heard the sound of a small plane about to fly over the resort. “Film training. You always pause,” as the conversation went on a fifteen second delay as the plane made it over his head. The moment felt like a small bite of awkward humor brilliantly found in Payne’s work, leaving both of us to chuckle as the plane became louder and louder as it went over our heads.

Jumping back to our conversation, in finding one of the locations for the film, Payne found the film’s biggest discovery, actor Dominic Sessa. Winning the part after over 800 submissions and countless auditions, Payne and his casting director Susan Shopmaker started to call up the drama departments at the schools they would be shooting at. “We said, “Are there any students there who would like to audition for our movie?” And they said, “Yes.” And then that’s where we found Dominic Sessa. He was on his way to being an actor.” Indeed he is, as I stated in my review out of Telluride from earlier this year, steals “every moment he is on screen” and delivers one of the best newcomer performances of the year.

Alongside Sessa, the two other major roles in Payne’s holiday comedy-drama were assigned to someone familiar with the director and someone new. For the role of Mary, the director had seen Da’Vine Joy Randolph in her incredible performance in Dolemite is My Name, and “made sure that the casting director made sure that I was going to meet Da’Vine,” knowing she was perfect for the role. As Mary,  Randolph is able to be the emotional core throughout The Holdovers, and in doing so, it’s “the best work of Randolph’s career.”  As for returning to work with Giamatti again for the first time since Sideways, Payne knew he was right for the part, as he stated jokingly, “The character’s name is Paul.” Diving more into their collaboration process in finding his character, he said “I just left it up to him. There are certain actors you cast because you’re curious how they’re going to do it. I mean, if you cast Meryl Streep in a part, you’re not going to tell her how to do it. You are then a filmgoer yourself thinking, “Oh, I’m so curious to see what she’s going to do with that part.” That’s how it is with Paul. I’m just curious to know what he’s going to do with the part. I’m there to just turn the camera on and let him go. My directions wind up being, “Louder, softer, faster, slower” for the most part.” By giving Giamatti this freedom and trust to make Mr. Hunham his own, he is able to deliver “a hilarious, nuanced performance,” ranking as some of the best work of his career.

As Payne started to spoon out the remaining bites of his Coke float, we discussed his fascination with his protagonists being broken souls, as Mr. Hunham, Angus, and Mary fall in line with the main characters in Sideways, About Schmidt, Nebraska, The Descendants, and Election. By the end of those films and The Holdovers, we don’t know if things will be one hundred percent peaceful for these characters but we have hope that they will be okay. Payne asked, “Who’s the perfect protagonist? I mean, who’s not broken in some way or needing completion in some way? Yeah, you know what? I appreciate your question. I know it’s not intentional. It’s just what I’m drawn to in terms of these literary, and I hope lifelike characters.”

The Holdovers opens with throwback title cards, set in the 1970s, using contemporary music to convey a mood of the snow past Payne has set up for us. It’s no secret that it is a movie showing its influences on its sleeve and Payne took influence from one film specifically in creating the tone of his latest film. “One movie that I think David Hemingson, the writer, and I both appreciate very much is Hal Ashby’s The Last Detail. It’s about sailors: two military policemen and one mentally challenged young sailor. But we liked the idea of very disparate people thrown into a circumstance and falling in love somehow. That’s what we took from it, I think. An unlikely love story.”

As the float started to turn into a sludge at the bottom of our glasses, we had time for only one more question. As The Holdovers is set during the holiday season, and many audience members will be checking out the film for the first time as they fly home within the next two weeks (“I hope so” was his response from that notion of everyone seeing together with their families), I wanted to know his go-to holiday movie. His answer was perfect. “The only Christmas movie I watch every year is, of course, It’s a Wonderful Life, which is a towering achievement of a film. It’s really a great masterpiece and I think it’s one of the finest American films of the 1940s. Every time you see it, it is to some degree the first time. You remember how good it is. But you don’t remember, oh my God, how dark it is or how beautiful it is. And that’s true of a lot of Capra. You think you’ve seen it and then you see it again and it’s the first time all over again. Watch It’s a Wonderful Life again. Watch Mr. Smith Goes to Washington again. Those are wonderful films.” At that time, we got up from our seats, picked up our empty glasses, and politely shook hands as I thanked him for his time. “Thanks for the conversation,” he said. “That was fun, and the float was pretty good too.”

Alexander Payne’s The Holdovers is now in theaters from Focus Features.

Photo: Seacia Pavao / © 2023 FOCUS FEATURES