Writing from the Heart: David Hemingson Talks About ‘The Holdovers’

Focus Features’ The Holdovers, which hits select theaters on October 27 and has a wide release on November 10, is like that gift you weren’t expecting under the Christmas tree - it’s a pleasant surprise. Starring inimitable Paul Giamatti as curmudgeonly teacher Paul Hunham, the film is an ode to celebrating the holiday spirit, in all of its forms. Dominic Sessa is Angus, the misfit Hunham’s left in charge of over the holidays. Da’Vine Joy Randolph is Mary, a cook with a voice of reason. Set during 1970, the film totally transports us there. Director Alexander Payne (Sideways, The Descendants) said they shot the film like they were “living in the '70s and happened to be making a film.”

Reminiscent of Dead Poets Society (1989) if Professor Keating woke up on the wrong side of the bed every morning, the bittersweet film reunites Alexander Payne and Paul Giamatti after twenty years. And they don’t disappoint. However, the man behind the keyboard of this heartfelt gem of a film is first-time feature writer David Hemingson. David has done a ton of television, including Black-ish, American Dad!, and How I Met Your Mother. With The Holdovers, we’re introduced to a new voice in the feature realm that is astute, funny, and earnest.

David Hemingson recently took the time to speak with Script Magazine about his writing journey with The Holdovers.

Sonya Alexander: You started out as an entertainment attorney. When did you definitely know you wanted to write?

David Hemingson: Two weeks in as an attorney, I was like, 'This is not for me.' I'd spent about $75,000 of my own money on law school. My Italian grandmother said I was too stupid to become a doctor, so she thought I should become a lawyer. I don't regret it. It was a great experience from an intellectual standpoint. It shook the Etch-a-Sketch on the way that I think.

SA: What skills from law school do you think help your writing?

DH: A predilection for organization and structure. I'm a huge outliner. Stephen King talks about two types of writers, planners and pantsers. Planners are the ones who write out every note. For example, John Irving in the novel world. I'm definitely a planner and I think law school amplified that. When I started writing TV what I would do... I'm kind of an autodidact when it comes to writing...I didn't go to film school...I would watch certain TV shows and break down as fast as I could the ABC stories on a grid and write down what was happening with each moment, with each character. Then look over it again for matrices and patterns...I'm a nerd!

SA: How do you feel your writing has changed since you first started writing?

DH: I've had a chance to work with some amazing writers and showrunners. I'm kind of restless. I started out writing for The Adventures of Pete & Pete on Nickelodeon, which was great. Then I went over to do some kid's animation. Then I worked on For Your Love with Yvette Lee Bowser where I learned multicam from a vet. Then worked with Steve Levitan at Just Shoot Me! Then I went to single-camera comedy on my own. Then I went to adult animation with Family Guy and American Dad! Then hard single-camera procedural. Then soft single-camera procedural. The more different genres I encountered, the more I internalized certain kinds of structural stuff that you don't even realize you're internalizing. Hopefully, that's not too byzantine an answer.

SA: The Holdovers is your first feature, right?

DH: Yes, it is.

SA: How did it come about?

DH: I wrote a pilot, just for my own edification. It was autobiographical, about my life as a scholarship student at a prep school. My manager, who was my agent at the time, told me it was too specific. 'I don't know what we'll do with this,' he told me. He’s been my rep for over 27 years. He gave it to a client of his, who gave it to Alexander Payne. He read it and loved it and called me up out of the blue. I almost hung up on him because I thought it was a joke. I'd been producing a show in Prague called Whiskey Cavalier and I'd been flying back and forth. I was dog-tired to the point of delirium. He called and I literally thought it was a buddy of mine pranking me. He told me he loved my pilot and asked me what I thought about writing a movie for him, with this logline - 'Odiferous, ocularly challenged professor at a boarding school stuck with these kids, one who's been abandoned by his mom while she goes on her honeymoon.' I broke it out. Would run stuff past him and he'd be like 'yes' or 'no.' He sort of directed me as a writer.

SA: How long did it take for you to write the first draft?

DH: First draft took about eighteen months. All of this stuff happened in the middle of COVID. I think he had another picture that ended up falling through. Other stuff was going on, but I just kept at it. What was great about it was I was learning along the way. He wanted to make a '70s movie. I knew I had to keep up with him. I started going to this place called CineFile Video, at the corner of Santa Monica and Sawtelle.

SA: I know that place, love it!

DH: It's a tremendous resource for writers. There’s a lot of stuff that drops off of streaming....stuff just evaporates off of streaming, you can't find it anymore. Even that threat to Turner Classic Movies was like an existential threat to writers. But you can always count on CineFile, these two guys JP and Greg. I told them I needed to write a '70s movie. They turned me on to Hal Ashby, Robert Altman, Bob Rafelson, Milos Forman. What about 400 Blows or Bande à part by Goddard? It has an improvisational style but that male friendship component. Alexander knows about 75 times more than I do about film history. He would also suggest films. I kind of went to film school on Alexander Payne's back…! [laughs]

SA: The movie totally immerses you in the '70s without being obvious.

DH: Alexander knew the tone he wanted. We discussed Vanishing Point, you know it?

SA: Oh, yeah.

DH: It was this B-movie my uncles wanted to see when I was a kid. They were both janitors at Wesleyan University. They snuck me and my cousin in in the trunk of their Oldsmobile Delta 88. We got out of the trunk, and there were these speakers on the windows. That was my most formative '70s movie experience. I thought the film was insane!

SA: Which character do you feel you relate to the most in The Holdovers?

DH: I relate to all of them. Angus is my pain, insecurity, and alienation. My parents got divorced in the late '60s, early '70s. It was a very hard divorce. I was in a single-parent household. My mom was an RN getting up at 4:00 a.m. in the morning. She'd get home in time to make me dinner. I was a latchkey kid. I had a hard time at public school. I was strange and bookish. Mary is my emotional truth. The way she feels about her son is the way I knew my mother felt about me. Paul's character is the guy who raised me after my folks split, my Uncle Earl. He was a WWII Vet who never finished college. He was a remarkably brilliant man. He spoke six languages, worked at the U.N. He had this incredibly unified theory of life. He gave me an unvarnished gospel that was baroque and profane....wonderful and deeply humanistic.

SA: This was Dominic Sessa’s first acting role. How was it working with him?

DH: That kid's a revelation. We looked everywhere, all over the English-speaking world. I'm also a producer on the film so I saw all of the auditions and the final rounds. There were like 60 or 70 kids. There was something in Dominic's eyes. He was just the kid. He'd never been on camera before. He was such a natural. He was a senior at Deerfield Academy where we were shooting. We found him in the Drama Department of one of the schools. Paul said he'd like to work with the kid. Dominic’s a sensitive, smart, decent kid and a brilliant actor.

SA: What should audiences take away from the film?

DH: That it's a love story.

SA: What do you feel you learned from this experience that you'll take on to your next feature?

DH: Never be afraid to go deeper. Right when you think you have the character figured out, find out what else we can know. Tell me more. Give me a bigger truth. Don't stretch for it. It can be a small, wordless moment. Show the vastness of the human experience in terms that are relatable and understandable. Don't be afraid to go small because therein lies the truth. 

The Holdovers will be available in select theaters on October 27, 2023, and everywhere on November 10, 2023.