Oscar-winning film The Holdovers now streaming on Showmax

Nominated for five Oscars, including Best Picture, Alexander Payne’s The Holdovers stars Paul Giamatti (Sideways, Billions) as a cranky prep school history teacher who is forced to remain on campus over the holidays with a grieving cook (Da’Vine Joy Randolph) and a brainy student (newcomer Dominic Sessa) who has no place to go.

Randolph won the Oscar, BAFTA, Golden Globe and Critics Choice awards, where Giamatti and Sessa also took home Best Actor and Best Young Actor respectively. 

Over a decade ago, Payne watched a somewhat unknown French film, Merlusse (1935), by the acclaimed filmmaker Marcel Pagnol. “I saw that film just once and it never left me,” says Payne. 

Payne felt that Merlusse, which tells the story of boarding school students marooned with a reviled teacher over the holiday break, would make a great premise for a new story.

(From left): Dominic Sessa, Paul Giamatti, and Da’Vine Joy Randolph in The Holdovers

As fortune would have it, a script would soon land on Payne’s desk that cemented the idea for the director. “David Hemingson had written a pilot script that took place in an all-boys prep school, and it was wonderful,” says Payne. “I called him up and said, ‘I don’t want to make your pilot but would you consider writing a feature script based on a different idea?’”

Payne usually writes his own screenplays – including Sideways and The Descendants, both of which earned him Academy Awards for Best Adapted Screenplay. So Hemingson remembers Payne’s script commission coming out of the blue. “I was incredibly flattered because he’s a personal hero of mine,” says the writer, who made his feature film debut with The Holdovers – and earned an Oscar nomination for it. 

Working with Payne over a three-year period, Hemingson drew on many of his own personal experiences to bring the world of The Holdovers to life. “My folks got divorced when I was five and I didn’t see my dad that much,” he says. “We didn’t have a lot of money and I wasn’t doing great in public school. My dad was teaching at this extraordinary private school in Hartford called the Watkinson School and my mom said, ‘We should go to the school, and it’ll give you a chance to get to know your father a little bit.’ So I went there for six years and a lot of the people that appear in the movie are composites of people I knew there. It’s such a different world, such a rarefied world, and there’s certainly a lot of money and privilege knocking around, but there’s also a lot of pain. Adolescence is a difficult time.”

Hemingson was also inspired by his close relationship with his uncle, Earl. “He was a remarkable man and he basically became the foundation for the character of Paul,” he says. “Although my uncle never finished college because he was in the army, he worked for the United Nations and conversed in eight languages. Some of the dialogue in the movie comes directly from him. It was that hard-bitten, hard-won wisdom that he gave me at a very young age, which I think warped me as a human being, in the best possible way.”

Dominic Sessa and Paul Giamatti in The Holdovers

The Holdovers marks Payne’s first period film, although he notes that, in some ways, it feels like something he’s always done. “In a way, I’ve been making 70s movies my whole career,” says the director. “I focus on what I hope are very human stories as opposed to stories of device, convention, or contrivance. I like having a protagonist and story who approximate real life much more than movie life. Also, I was a history major in college and I still read a lot of history. Now I see that making period films is the closest thing you can do to time travel, so to have that experience was lovely.”

Paul Giamatti in The Holdovers

Ever since 2004’s Sideways, Payne and Giamatti had hoped to collaborate again. “That was perhaps the happiest collaboration I have ever had with an actor – and I have had a lot of good ones,” says Payne. “I think Paul Giamatti is the greatest actor… Every take Paul does is completely truthful and completely new. There is nothing he can’t do.” 

As proof, Payne once challenged Giamatti to read from the Omaha phone book for a live audience at a benefit event in Nebraska. Of course, once the actor started, he brought the house down.

Giamatti is just as complimentary about Payne. “Alexander knows how to deal with every actor individually, and that’s pretty remarkable. He’s also an amazingly good host and learns everybody’s names, including all the extras’ names. There are just so many things that he’s great at.”

Randolph echoes this. “Alexander does such a great job of combining comedy with pain and drama,” she says. “He has such vast knowledge without being intimidating. He truly loves this and sometimes gets giddy between takes, dancing, smiling, or clapping his hands like a little kid. I found that very humbling. This can be a very hard job, so that youthfulness, true passion, and love for what he does is one of the main ingredients for why his projects are so wonderful.”

Giamatti came to the role with a love of ancient history like his character, along with an intimate understanding of the academic world. This was owed in part to his father, A Bartlett Giamatti, who served as president of Yale University. 

“I went to a prep school like the one in the movie,” he says. “My father was a professor. My mother was a teacher. My grandparents were all teachers. Everybody in my family is a teacher or an academic. It’s a background I understand and have a rapport with.”

(From left): Dominic Sessa, Paul Giamatti, and Da’Vine Joy Randolph in The Holdovers

Finding the right actor to play the key role of Barton Academy student Angus Tully – a damaged kid who’s been through a lot in his life – was always going to be the film’s biggest challenge. 

“We had about 800 submissions from around the English-speaking world,” Payne says of the casting process. “Finally, the casting director, Susan Shopmaker, and I looked at each other and said, ‘Well, time to do what we talked about at the start of the process. Let’s call up the drama departments of the schools where we’re actually shooting and see who’s there.’ And damn, that’s where we found Dominic Sessa, an actual senior at Deerfield Academy.” 

Sessa was a star in the school’s drama department but had never performed on screen before, so Payne auditioned him several times to make sure. “What was impressive was that it was not just his first leading role in a film but it was his first time ever in front of a camera,” notes Payne. “He’d never been in a movie before, not even in a short film. There are so many actors who have to learn all of the techniques, like how to be comfortable in front of the camera and how to focus on their role despite being surrounded by 50 people and lights, microphones, and a camera. Some people are just born with it, and he’s really got a natural, God-given talent for film acting.”

Sessa couldn’t believe he was working on an Alexander Payne film, and says the experience was full of revelations. “I think the biggest surprise for me was how much agency Alexander allowed me,” he says. “He gave me a lot of freedom and liberty in creating the role.” 

The Holdovers has a 97% critics’ rating on Rotten Tomatoes. As Mashable says, “The Holdovers is a terrific Payne film, bursting with sharp laughs and searing sweetness.”

“What’s beautiful about this movie is the way it transcends ageism, racism, and gender,” says Randolph. “Sometimes when you’ve hit rock bottom, you’re open to anything to seek relief wherever you can. You would talk to a stranger if that meant that someone would listen to you.”

“I love that the film is about having that willingness to dig deeper, to try to get to know somebody and understand them even though, on a surface level, they’re very different from you,” says Sessa. “We’ve all had these things that have happened in the past and they’re still eating at us. But these characters help each other let the past go and move forward.”

Watch the trailer Watch Randolph win the Oscar

Watch The Holdovers on Showmax.