Sideways meets A Christmas Carol in Alexander Payne’s latest project.

Genre: Drama
Premise: A professor at a prestigious all-boys academy in 1970 is stuck babysitting the one “holdover” over Christmas break, a student whose parents have ditched him for the holiday.
About: This is the big re-teaming (it’s Re-teaming Week here at Scriptshadow!) of Alexander Payne and Paul Giamatti (Sideways). The writer, David Hemingson, has been writing on TV shows since the 90s! This is a major departure for him and a huge new direction for his career. The Holdovers is filming in New England as we speak.
Writer: David Hemingson
Details: 117 pages

It’s crazy how dramatically one bad movie can damage a filmmaker. Even if that filmmaker has had decades of success. Payne, a darling in the indie world and a two-time Oscar winner, hasn’t made a movie in five years. All because his last film, Downsizing, was too weird and lacked a compelling plot.

But alas, we should not be punishing those who take creative risks. We should be rewarding them! In theory, at least. Let’s be honest. We’re all supportive of taking risks unless those risks turn out to suck hay bails.

50-something professor, Paul Hunham, described as “a heap of rumpled corduroy” is the most hated professor at Deerfield Academy (circa 1970). Paul is the only professor unafraid of the school’s prestigious alumni, as he proves by flunking a senator’s son, which prevents that student from being able to go to Princeton.

Because Paul is such a Scrooge, he doesn’t have any friends. Therefore, when winter break comes around, Paul has nowhere to go, and is assigned to take care of the “holdovers,” those kids who couldn’t go back to their families over Christmas for various reasons.

At the top of this reject list is 15 year-old Angus Tully, whose presence as a holdover is the direct result of his mom getting re-married to some loser who would rather go on a honeymoon than be around his new step-son. And hence the chip-on-his-shoulder Angus must stick around at a dead campus with nothing to do. A kid’s worst nightmare.

To make matters worse, all the other holdovers leave. That means it’s ONLY Paul and Angus left. And neither of them want to be anywhere near each other. They endure this for a while, having meals and studying under a series of angry glares. But they ultimately get invited to a Christmas party by a fellow female teacher, Miss Crane, who Paul has a crush on, and things pick up a bit. This begins an unexpected friendship between Paul and Angus, even if it is one explored primarily under duress.

The Holdovers feels like it’s made for a targeted audience. By that I mean, people who have gone to school at one of these all-boys academies. It’s very specific in that way, which made it hard to relate to.

And, unfortunately, I think the script made some questionable creative choices that prevented it from being better. For one, the dynamic between Paul and Angus wasn’t charged enough. Angus kind of doesn’t like Paul. Paul kind of doesn’t like Angus.

I don’t like “KIND OF” conflict. I like “ACTUAL” conflict.

There was another kid named Jenesen who was a total brat. Just a bad dude. He felt like a much bigger adversary for Paul. Those two would’ve gone at each other relentlessly and, therefore, made for a better script, in my opinion.

Speaking of, the original setup, which had five kids on holdover, sounded much more promising. Now you’ve got Dead Poet’s Society meets The Breakfast Club. A coming-of-age film with a group of kids getting in trouble. That’s a winning formula that has delivered time and time again.

The mismatched duo is also a winning formula. But only when the two opposing characters have clear conflict with one another. And like I said, these two only have “kind of” conflict with each other.

Taking this one step further, one of the big themes of the script is entitlement. These are all rich kids who have been handed everything in life. So keeping them here at this rich kid’s school doesn’t really test that. What would’ve been better is if they had to leave the school for some reason (it was temporarily shut down over the break) and stay in town, in a world that’s completely foreign to what they’re used to.

But again, we didn’t even have a group of kids. We decided to go with one kid.

I know it’s stupid to write reviews whose main focus is, “This is what I would’ve done!” But I bring it up to remind screenwriters that you always have choices in your story. And you should be asking yourself, “Is this the most dramatically interesting choice? Is there a different route that’s potentially more entertaining?”

We get major tunnel vision as screenwriters. We get so stuck on that original idea we wanted to write that we don’t see there’s a much better version of it right around the corner. This especially happens if you’re drawing on your own life experiences. You’re likely to lock in on exactly what happened to you and write that story only. Which is myopic. You have to be more dynamic as an artist.

I brought this up a couple of years ago with the movie “The Big Sick.” Now to be clear, The Big Sick was a great movie. I don’t think it’s bad by any means. But if you’re looking at the script objectively, they missed a much more dramatically interesting opportunity.

That film was about how Emily goes into a coma and Kumail has to deal with her parents during the experience. But Kumail had next-to-zero conflict with her parents. So that storyline wasn’t very compelling. Meanwhile, Kumail’s parents did not want him marrying a white woman under any circumstances. They wanted him marrying a Pakistani. Therefore, the better person to put in the coma would’ve been Kumail. That way, you would’ve put the characters who had the most conflict with each other – Emily and Kumail’s parents – around each other the whole time.

Of course, that wasn’t what happened to real-life Kumail and real-life Emily, and therefore it would’ve been difficult for them to imagine that version of the story. But the point is, you shouldn’t lock yourself into a particular storyline without considering if there’s a better dramatic option.

With all that being said, The Holdovers does come together in one of those warm Christmas-y ways where you feel good cause everyone takes down their walls and connects with one another. I can imagine watching this on Christmas Eve and feeling that good “everything’s right in the world at least for this moment” feeling that other good Christmas films like It’s A Wonderful Life give you. It’s just a hard script to wrap your head around because it keeps changing into different movies as it goes on and by the time you figure out what the actual movie is, you’re thinking, “Why didn’t we just start with this?”

[ ] What the hell did I just read?
[ ] wasn’t for me
[x] worth the read
[ ] impressive
[ ] genius

What I learned: I know some of you are terrified of character descriptions. I was once terrified of them as well. So here’s a tip. Don’t write clever character descriptions unless you’re good at them. And if you do, don’t overcomplicate them. Clever character descriptions from writers who aren’t naturally good at them are too long and come off as try-hard. Here’s an example of what I mean: “TREY, 31, has a dollar to his name but makes up for it with a million dollar smile.” What is this other than, “Look at me?” It emphasizes clever over information. If you’re going to be clever with a description, do it AS SIMPLY AS POSSIBLE. That’s why Paul’s description is so good. “A heap of rumpled corduroy.” Five words and we get it. The simpler you keep the clever description, the more likely you are to pull it off.

What I learned 2: If you want to attach Paul Giammati to your project, write a Christmas movie. This is his third Christmas movie (All is Bright and Fred Claus are the other two). He obviously likes the holiday.