How "The Holdovers" writer was inspired by Michelangelo to create a "broken" holy family

Years ago, while visiting Florence, Italy’s famed Uffizi gallery, screenwriter David Hemingson found himself captivated by the famed painting of the holy family known as the Doni Tondo. That wouldn’t be noteworthy, given the work's notoriety, except for its role in inspiring “The Holdovers" and the three lonely people at its heart.

Like Michelangelo’s masterpiece, “The Holdovers,” directed by Alexander Payne, is a period piece set inside a memory bubble. The film rewinds to December 1970 and the cusp of Christmas break for Barton, an Ivy League feeder school for boys in suburban Massachusetts. While most students head home, the kids who cannot remain on school grounds, supervised by raspy classics teacher Paul Hunham (Paul Giamatti), the least suited for the job.

Paul is not a people person, preferring to draw meaning from the ancient Romans and Greeks instead of connecting with the people around him. Somehow he wrangles a group of five surly boys until one of their rich fathers comes through and whisks away four.

The doubly abandoned remainder, the moody Angus Tully (Dominic Sessa), is miserable to be stuck with his teacher and the school’s head cook Mary Lamb (Da’Vine Joy Randolph).

Trade these three for Joseph, Mary and the infant Jesus, and . . . to be honest the parallels still might not be all that clear. Both Paul and Hemingson might implore us to look a little more closely, though. “In an analogous sense, it boils down to: Can I make a family at Christmas from these three very broken, very different people?” Hemingson told Salon in a recent Zoom interview.  “I wanted to enfranchise all of these characters and have it be almost the Holy Family.”

Only in this Christmas scene, father and child do not like each other, and the mother is grieving a son who was killed in the Vietnam War. But all of them are hurting in ways they only come to understand by spending time alone, together.

“The Holdovers” treads that ambiguous middle ground between comedy and drama as these three grieving people slowly grow on each other, drawing comfort from their company. Helping this along is another inspiration taken from the Doni Tondo, in that Hemingson thinks of Barton’s temporarily vacant Barton school grounds as “a biodome.” 

“Boarding school is almost like a hermetically sealed environment, with very distinct rules and hierarchies,” he said. “There's been a long sort of romantic history with boarding schools — and the production value is always good at boarding schools. So I think it's a combination of the hermetically sealed sort of environment and the rules, which also give rise to drama.”

Hemingon’s movie joins a cadre of critically acclaimed and award-nominated movies about prep school life – “Dead Poets Society,” “Goodbye, Mr. Chips” and “Rushmore,” to name a few. He’s also drawing from what he knows, having attended a place like Barton, only not as one of the rich kids. He was a scholarship student.

Before writing “The Holdovers,” series TV was Hemingson’s main medium.  He served as a writer and executive producer on such shows as “American Dad” and “Just Shoot Me!” and created the 2019 ABC series “Whiskey Cavalier.” This feature was originally intended as a pilot pitch before Payne got hold of it, Hemingson said. But regardless of which format the story would have taken, "I really didn't want to do ‘Dead Poets Society,’” he stressed.  

Instead, Hemingson consciously positioned “The Holdovers” to examine class and race. He confesses to putting a bit of himself in Angus and Paul, although the main inspiration for Giamatti’s character was Hemingson’s uncle Earl (to whom he gives credit for inspiring lines like, “For most people life is like a henhouse ladder: s**tty and short”).

Da'Vine Joy Randolph in "The Holdovers" (Focus Features)Mary, meanwhile, is a tribute to his mother, who was a nurse. Mary views spending her first holiday without her son Curtis at Barton as a way of remaining close to him. Curtis was drafted into the Army while his classmates went on to Ivy League schools because, as Mary tells Paul, he had the grades but she didn’t have the money to send him where he wanted to go.

“I wanted to write something powerful about the maternal experience, and my mother was my touchstone,” Hemingson said. From there he began thinking about what life was like for the working-class people he grew up with, and “about the truth of the people who worked at my prep schools. And most of them were Black and Eastern European women.”

Mary, he explains, is his effort to acknowledge how different life was for the Black kids he grew up with. “I remember looking around and noticing that basically poor kids and kids of color were the ones shipped off to Vietnam or getting killed in a disproportionate way. Then I started doing research into it and I realized exactly how disproportionate it was.

“So I did that historical research,” Hemingson continued, “and I decided to frame Mary’s journey kind of as a thought experiment: what would happen to my mom if I had been killed?"

Want a daily wrap-up of all the news and commentary Salon has to offer? Subscribe to our morning newsletter, Crash Course.

Taking this unconventional route into what looks like a standard prep school reminiscence earned “The Holdovers” multiple Academy Award nominations, including best picture; best actor for Giamatti, who has already won a Golden Globe and a Critic's Choice Award for his performance; best film editing; and a best original screenplay nod for Hemingson.

Randolph’s Oscar nomination for best supporting actress also follows Globe and Critic’s Choice wins for her portrayal of Mary, a performance that travels between gentle stoicism, worn-in laughs and, when Mary reaches her breaking point, a sorrow that turns her inside out.

“Because it wasn't my lived experience, it was really important for me to create as much space as possible for Da’Vine to step in and bring her experience to it as an actor, and as a woman and a Black woman,” Hemingson said. “I very much wanted to make sure that . . . she had the latitude to do it. And she did an incredible job.”

Asked what the screenplay Oscar nomination means to him, Hemingson visibly choked up. “It's thrilling,” he said. “Like, I just think of my mom and how I wish she was around to see it.”

"The Holdovers" is streaming on Peacock.