Interview: David Hemingson On Turning Past Relationships Into ‘The Holdovers’

When the credits began scrolling at my screening of The Holdovers the first two words I thought of were “effortlessly enjoyable.” And months later I fully stand by them. This observation is strictly in a positive light, because the creative and emotional effort needed to create it found in every frame of the film – from the performances and cinematography to the art direction and editing. There’s something very personal, familiar, and genuine about The Holdovers that wraps around you like a cozy warm blanket on a cold day and makes you want to live in this world.

The film, from director Alexander Payne, tells the story of Paul Hunham, a professor (played by Paul Giamatti) at a boys boarding school where he must spend his winter break watching over a group of boys who have no place to go for the holiday. The loathed professor forms an unexpected bond with the school’s head cook, Mary (Da’Vine Joy Randolph) and a troublemaking student, Angus (Dominic Sessa).

I spoke with The Holdovers writer David Hemingson (our full conversation can be found in the video below) about why audiences have connected so profoundly with the film and its characters. The performances, which have been recognized throughout awards season as some of the year’s very best, are certainly a huge part of the equation, but Hemingson’s words are the source of the characters’ sincerity. The reason behind that may be found in the origins of the trio since Hemingson mined real life inspirations when writing them.

“I wanted to have that conversation with myself and that made the movie a joy to write because it forced me to examine my own relationships,” shared Hemingson. “This kid (Angus) I knew was going to be my lead – he was going to be my emotional analog from when I was a kid,” said the writer. “Mary is emotionally and kind of spiritually my mom.” 

In addition, Giamatti’s character Paul was “basically my uncle,” a man Hemingon described as “this incredibly stalwart, tough, salty World War II veteran who kind of raised me when my folks split.” Hemingson’s love for the characters and unique personal connection comes through in every scene, but avoids being exclusive. Quite the opposite, instead they are delightfully engaging and feel like family.

The Holdovers finds a wonderful balance of humor and pathos, but Hemingson categorizes it in a way that may at first be unexpected but taps directly into its heart. “I just wrote this love story from the heart,” said Hemingson. “I think love stories can take different forms,”

While aspects of a typical romantic relationships are present, the film’s love story is based in a universally relatable experience – pain. “This is about three people who gradually reveal to us and to each other that they have their own personal crises and their own burdens to carry, but they find a way to get through it together,” explained Hemingson. “They share with each other that kind of emotional availability, an imperfect emotional availability.”

During our conversation, I mentioned to Hemigson that half way through the film I had already created a list in my head of people with who I needed to share this delightful film. It included my all-time favorite viewing partner, my wife, and my long-time film friend who sadly passed away, but who always come to mind when I see a special piece of cinema.

Under its unassuming surface is a comedy, a drama, a love story, a coming of age story and a love letter to the 1970s and films of that era… to name a few. It is no wonder why the film tops my list of the Best Films of 2023.

Be sure to check out my entire fascinating conversation with David Hemingson in the video below. During our talk we discuss much more about The Holdovers, including working with Payne, his “freaky history” with Giamatti, as well as his favorite holiday films, and some talk about his series with gave Bradley Cooper his first starring role, the sadly little known but much loved, Kitchen Confidential.

If you have not seen The Holdovers yet, find someone who ‘gets you’ and share this love story with them. It is playing in theaters and streaming exclusively on Peacock.