David Hemingson was in production on his latest TV show when he got a phone call from someone who claimed to be Alexander Payne. The seasoned writer, who at that point had worked exclusively in TV and was the showrunner on ABC’s Whiskey Cavalier, assumed it was a friend of his playing a trick on him.

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“I’m just a slobbering fanboy when it comes to his work,” says Hemingson now. “It’s surreal that you spent many years as a writer and one of your heroes calls you up and says, ‘Would you be interested in doing this?’”

Payne was interested in making a movie set at an East Coast prep school, and had read Hemingson’s pilot script about an “optically challenged, kind of odiferous professor” forced to stay at school over the holidays with a band of misfit students who have nowhere else to go. For Payne, Hemingson scrapped the pilot and began telling the story, very much based on his own prep school experience, as a feature film.

It’s now The Holdovers, a festival hit opening in select theaters on October 27, ahead of a wide release on November 10. The charming throwback to the movies of the 1970s is a wry but warm comedy about outsiders who find connection during the holiday season, featuring deeply moving performances from Paul Giamatti, Da’Vine Joy Randolph, and newcomer Dominic Sessa. As Hemingson describes it, the movie is “a love story between these three people who are each broken in their own way.”

The film also represents a new step for Hemingson, who, after a long and comfortable career in television, has now stepped into an entirely different arena—and found Oscar buzz to boot. “I’ve been waiting for this my whole life,” says Hemingson. “I feel like [sometimes] you wait for things and they don’t arrive when you want, if at all.”

Hemingson got his start in Hollywood as an entertainment lawyer, working for the firm Loeb & Loeb in financing and agency and actor agreements. Eventually, like so many others, he realized what he really wanted to do was write. “God bless my mother—she was the only person in my family who really understood that I wanted to be a writer,” says Hemingson. “I’d fallen in love with movies as a kid, and she’s the only person that said, ‘Go for it.’” He says he got lucky and found an assistant writing job on the ’90s Nickelodeon TV series The Adventures of Pete & Pete soon after quitting his job as a lawyer. He continued to climb his way up as a TV writer, with stints on Just Shoot Me!, American Dad!, How I Met Your Mother, and Don’t Trust the B---- in Apartment 23.

He had an overall deal with ABC and was known for being able to work as a creator and showrunner in multiple genres, but being a writer-for-hire wasn’t enough after a while. “Television, to begin with, is art by committee…. I just felt really blessed and lucky to be working for as long as I have as a writer, but I wanted to break out and do something that was uniquely my own,” he says.

So in 2017, he wrote a pilot for a show set at a New England prep school similar to the one he’d grown up attending. Initially, the series was about a young man bonding with his estranged father, who worked at the school. It also captured the young man’s struggle with his parents’ separation. “I had this kind of fascinating childhood that was really kind of fraught but very loving, but kind of a collision of class and culture,” he says.

The Holdovers feels very personal, with details that could only have been pulled from someone’s lived experience at an East Coast prep school, which is exactly where Hemingson found himself after his father got a job at the Watkinson School in Hartford, Connecticut. He spent six years at the school, but coming from a blue-collar background, he always felt a bit like an outsider. “I wanted to capture both the grandeur and the Currier & Ives sugar-frosted thing, but also the inequality and the privilege and the silent codes that are run almost like software, that people never deviate from,” he says.

The Holdovers is set at the fictional Barton Academy, just before winter break, when most of the students are preparing to head home for the holidays. A cranky history teacher named Paul Hunham (Giamatti) has been asked, along with school cook Mary Lamb (Randolph), to watch over the handful of students who have nowhere to go over the holidays. Paul butts heads with one rebellious student in particular, Angus Tully (Sessa), who is struggling with both the loss of his father and his mother’s new relationship.

Hemingson’s own parents’ divorce was also woven into the story. “They split up very acrimoniously in the late ’60s, and that was really traumatic, tectonic,” he says. He admits that “the Angus character is a lot of me—just this kid who’s sort of pushed off axis by his circumstances.”

Paul, whom Hemingson describes as a “shattered romantic,” is inspired by his uncle Earl, who stepped in as a pseudo father figure when Hemingson’s father wasn’t around. “He was so hard-bit and so tough, and his language was so fantastically comedic and baroque,” Hemingson remembers. “I kind of absorbed all that as a kid, because you worship that father figure, and he was there for me. I wanted to reflect that back and tell the story of this remarkable man.”

Mary, who caters to this group of privileged men while mourning her son, who was drafted to serve in Vietnam, is based loosely on Hemingson’s own mother, with her story inspired by the socioeconomic divides he witnessed as a child. “I’m not old enough to have been in the Vietnam War, obviously, but all the guys that I knew growing up, their brothers or uncles—a lot of them had gone. And I noticed it was mostly poor kids and Black kids who were going,” he says. “You see it, and you see the systemic issues and the injustice…. And I started thinking what it would be like for my mom, who loved me so ferociously, to lose me. So I channeled that.”

Hemingson’s script brings these three characters together as they attempt to make the best of a lonely holiday season. He peppers the script with other stories pulled right from his own experiences, like witnessing a kid break his arm in a tumbling gym, “almost in defiance of his parents,” at his own son’s birthday party.

And though many of the details are pulled right from his life, Hemingson says Payne pushed him in the formation of the script. “He would ask the hard questions, and that’s sort of his methodology,” he says. He would also reference tons of films that Hemingson would then watch as he was writing, including The 400 Blows and other French New Wave films for their sense of disconnectedness, as well as Bicycle Thieves for that father-son relationship.

Hemingson has worked with numerous directors over his career and has stepped into the role himself for television, though he admits he doesn’t enjoy it “because of the enormity of it.” “My friend Dean Parisot once said, ‘Being a director is like being pecked to death by chickens. Everybody wants something from you all the time,’” he jokes. But Payne lived up to his high expectations. “The way he deals with that, with such grace—he’s a real coat-and-tie director: He gets dressed up and you don’t blow your day,” he says. “He’s so confident, and justifiably so, in his own vision.”

After this experience with Payne, there’s no turning back for Hemingson. “It spoiled me,” he says. “I want to do stuff that is grounded in real human emotion, but can find those heightened spaces so that it’s super entertaining, because I think the only crime is really to be boring. You have to entertain people…. I don’t see anything else. This is just what I want to do.”