'The Holdovers’ Movie: Christmas break at a New England prep school

9 min read

Ok, now picture this if you will. It’s the Christmas break at a New England prep school, a grumpy teacher stays on campus to look after a small group of students without holiday plans. He develops a unique connection with a clever yet troubled troublemaker in an unexpected twist. Alongside this, he forges a bond with the school's head cook, a grieving woman who recently lost her son in the Vietnam War. This isn't reality tv, it's a movie I watched and wanted to share with you all.

Welcome to That's Life, I Swear. This podcast is about life's happenings in this world that conjure up such words as intriguing, frightening, life-changing, inspiring, and more. I'm Rick Barron your host. 

That said, here's the rest of this story 

We all love a good movie. Particularly a movie that doesn't seem to convey a 'must see' appeal about it. Movies that fit that category are called 'sleepers' and 'The Holdovers' fits that billing. It's like 'The Poet Society' or 'Love Actually'. 

The Holdovers cast: Dominic Sessa, Paul Giamatti, & Da'Vine Joy Randolph.
Courtesy of: Time Magazine

"The Holdovers" unfolds as a poignant narrative, weaving together the lives of three complex individuals—Paul, Angus, and Mary—portrayed by the talented Paul Giamatti, Dominic Sessa, and Da'Vine Joy Randolph. All three of these characters, find themselves thrust into the barren confines of an empty boarding school during the fading days of 1970. 

The individual who was the screen writer for this movie was David Hemingson. Some of his other past work include being a producer and writer known for Whiskey Cavalier (2019), Kitchen Confidential (2005), Don't Trust the B---- in Apartment 23 (2012) and Just Shoot Me!

From my view, The Holdovers, represents David’s finer pieces of work. 

Interesting point about this movie is David took characteristics of people he knew, and used them as guidance to build the three main characters in the movie.

David Hemingson. Courtesy of: Los Angeles Times

During an interview, David Hemingson shared his thoughts on how he weaved his parent's personas into the movie, along with someone else who gave him purpose to become a writer. 

As David started the conversation, he shared how his parent's divorce "ended." He quickly amended his thought by saying 'ended' was far too neat of a word. He altered the ending of his parent's marriage in more descriptive words when he said, 'it exploded'. 

I'll never know the particulars, but here's the "easy-to-read" version he said: my dad couldn't stay put, and my mom couldn't let him go—until she did. And doing so nearly destroyed her. At the time, is father was splitting time between teaching and shipping out as a merchant seaman. David's mother was working as many hours as she could as a registered nurse at Mt. Sinai Hospital in Hartford, Conn. 

Even with child support, the family was always on the edge, a razor's edge if you will. David's mom wanted to preserve some sense of normalcy, so she took the daybreak shift in the ICU, getting up at quarter to four in the morning so she could be home in time to make him dinner when he rolled in from school.

School was a challenge for David. What teenager doesn't go down that road? He found that period to be awkward and scattered for him. It didn't help him being a young kid with ADHD, so the social dynamics were challenging for him in the best of times and just got worse in the wake of the marital meltdown. By the time middle school was approaching, he hit the brakes and just stopped going. His mom would wake him at dawn, feed him breakfast, and make him promise not to go back to sleep. 

David promised his mom he wouldn’t fall asleep, while mentality crossing his fingers behind his back. He confessed that upon hearing his mom’s car leave the driveway for work, he'd pass out for another three hours. He loved passing his free time listening to Beatles records, or hoping into the bathtub and soaking until his hands got pruned. This deception continued for a month until the school finally noticed his epic run of truancy. Something had to be done.

Earl Cahail. Courtesy of: Time Magazine

That "something" came in the form of Earl Cahail. Earl was married to David's mother's older sister, Ann, and they lived on the lower east side of Manhattan. David vaguely recalls overhearing his mom over a hushed phone call talking with Earl centering on "what to do about David" 

Shortly thereafter that phone call, one Saturday morning, Earl was in their driveway, climbing out of his old Plymouth Duster, mopping his brow and cursing the 120-mile drive from New York City. From that day forward, it was a drive Earl would make nearly every weekend over the next decade.

Like his father, Earl left school to serve in World War II. Unlike David's father, Earl never went back to school. Instead, he took the route of job hopping his way around the world in those post-war years, finally ending up as the United Nations Office of Public Information manager. Earl was shy of six feet tall, pot-bellied and bald with jug-handle ears that supported a pair of thick Buddy Holly glasses. Earl wasn't what you would call Hollywood's version of a boyhood hero. Nope, instead David saw him as being ten times cooler.

Earl intrigued David. He knew everything there was to know about books, music, dogs, chainsaws, shotguns, Chinese food, and profanity. Quite a laundry list to share. He spoke, swore, shot, and cooked like no other person he had ever seen. Earl taught David how to swing a hammer and draw a bow. He fed him the classics and the National Lampoon, jazz and rock and roll, in equal measure. It was as if Earl wanted to share with David, everything he came across his life.

David said that one of the best things he liked being around Earl was he didn't feel sorry for him. There were so pity pats on the head—quite the opposite. Earl told David that life will be constant lessons. One lesson is that life will not always give you a helping hand or meet you half ways. In most cases, you'll just get a finger. 

He told me I was lucky. Lucky that I had a mother who worked harder than was humanly possible to support me. Lucky that I had a father who—although we were no longer close to one another—loved me deeply and worried about my welfare.

Earl was always busy, that said he hated laziness, so every waking moment the time that he and David spent together, was filled with something useful: chores or study or some form of exercise, usually push-ups, leg-lifts, pull-ups—all of which I would do while he supervised, usually with a Scotch in his hand. 

David shared how once a month on a Saturday morning, Earl would take him down to Wethersfield Cove and row us out into the swift water of the Connecticut River. 

While waiting for the catfish to show an interest, he'd tell me about his epic life. He described in vivid detail his years growing up in "genteel poverty," busting his ass on his family's rocky stretch of land (he called it a "stump farm"); summers sweated away as a "galley pot walloper" on the Black Ball Ferry line. David was taken by Earl being such an open book, but not always.

Earl talked about nights on Saipan, where, as a scared G.I., he would be gripping his rifle and scanning the tree line while praying that the war would end. When David asked for more information about World War II, Earl got quiet and veered off to another topic. Not surprised Earl went silent about the war. Most vets do, and for good reason.

Complex jobs, lean years, impossible adventures: Earl shared the unvarnished truth of his life with David. Language—and storytelling—became the great, binding force between them. Earl gave David inspiration with his storytelling, which is why he decided to become a writer.

By sharing his background, insights, and his time, David felt Earl had rescued him from the overwhelming weight of his history. Earl guided David to such an extent that when the opportunity for a scholarship at Watkinson came his way, a distinguished local preparatory school, he no longer felt like the youth concealed in the shadows. With Earl's hard-nosed demeanor and learning about life's sometimes tricky lessons, David felt transformed into an individual with a strong sense of discipline and self-esteem. He had a compass that pointed North.

With that they had shared together, it would be a fair guess that David saw a father figure in Earl.

For the next few years, as David navigated his way through prep school life, Earl guided him, constantly reminding him of his good fortune and pushing him to achieve academically. 

When David's mother would come home from a weekend shift, he'd make damn sure that dinner was on the table for her. One evening as David's mom said good-night, both he and Earl watched her climb the stairs to head to bed early to get ready for work the next day. Earl told David: "Be worthy of that." Deep in his heart David knew he had to be. Short of that would mean he would've betrayed them both.

Actor, Paul Giamatti. Courtesy of: Indie Wire

David reflected when it came time to write the screen play, he explained how he weaved three people he knew into the main characters of The Holdovers. Paul Giamatti's character in, the hard-nosed, unfriendly professor of ancient civilizations—a man with a hard candy shell and a chewy caramel center—he channeled Earl, just as he channeled his mother's immense strength and heartache and love into Mary. Angus would become a version of himself—a little older but no less of an outsider, hungry for guidance and connection—loving a brilliant and mysterious father from a distance.

David saw Earl as a tough guy but noted he was ultimately a man of immense kindness who understood human frailty and forgave easily. 

Through the various jobs Earl had in his career, he gained an education about life that no Ivy League degree could ever offer. He was David's best friend, his Merlin, his savior. When he died at 94, he left David with three guiding principles: 

·       Nothing comes free in this life, so nothing is without labor 

·       Do the right thing and fear no man 

·       And there is only one toast when you raise your glass: love and beauty—because those two words are the only things in this life that truly matter.

What other philosophy do you need? 

What can we learn from this story? What's the takeaway?

"The Holdovers" approaches connection with genuine sincerity, emphasizing the potential for saving or assisting each other if we only take the time to listen. While the film boasts deceptive cleverness and humor, it also highlights Director Payne's innate understanding of the impactful nature of silence. Paul Giamatti effectively delivers monologues on the significance of history, but the true essence of the movie lies in the central trio's shared glances and subtle gestures.

Labeling this film as a Christmas movie may seem unusual, given its unexpected departure from Payne's usual style, with past movies like Downsizing, The Descendants, and The Last Shift. The film embraces holiday elements with abundant decorations and the frequent inclusion of traditional carols in the soundtrack. The movie’s theme captures the spirit of the season by portraying the need to belong to something greater, the sudden generosity inherent in human nature, and the simple ways in which we can touch each other's lives.

In my book, "The Holdovers" is emerging as a potential new holiday classic. It's similar to the message from another beloved Christmas film, offering a poignant reminder that no one is a failure who has friends…It’s a Wonderful Life. 

Well, there you go, my friends; that's life, I swear

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