We Writers Should Learn from This Oscar-Winner, Even If It Does Get Lost to History

Whether it was half-plagiarized or not, I adored The Holdovers.

Vices. Hypocrisy. Secret motives. Each element of the screenplay — from plot to character to dialogue — is so tightly woven that it almost feels criminal to rip out the individual parts here and put them under a microscope. 

Great writing is tower of cards. Ace of spades here. Diamond there. They build on one another until you realize you are laughing only because the main character said “candy cane.”

This question here is, as always, what can we writers learn from the film? 

Here’s what I took:

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1. Use more attention-grabbing words

Writers tell stories. Sadly, we tell them to inattentive human beings with flawed human brains.

Average words are often dismissed by the vigilant guard of our minds. 

How do you pass this guard? A robust vocabulary.

Throw in a few words we rarely, if ever, hear.

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2. Find exactly-right comparisons

If a picture is worth a thousand words, the right comparison has to at least be worth several hundred. “Blue” eyes are no match for sapphire. A “treacherous” journey can’t match the terror of walking into the mouth of Hell. 

Holdover Screenwriter David Hemingson (formerly of Nickelodeon) knows this, which is likely why his movie is saturated with ripe similes and metaphors. 

Through the mouth of our main character, these pack a serious punch. 

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3. Allow meaning to change over time

Toward the end of the movie, our impression of the main character — a highfalutin, do-gooding, above-it-all teacher — rapidly disintegrates. 

He scolds a student for lying. Then, he turns around and lies to a stranger.

The student wants to know why. 

Here’s what plays out: 

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Lastly, a confession.

In many ways, this newsletter writes itself. 

It’s hardly risky to applaud a film which has already been awarded Best Original Screenplay by the most prestigious organization in cinema. 

The hard part, of course, is implementing the lessons. 

By making these observations, I have given myself homework. By reading them, you have accepted the assignment as well.

1. Use more attention-grabbing words

2. Hunt for better companions

3. Let the meaning of your work change over time

All of these require a level of patience and dedication the average writer does not have. 

The great ones, however, find the time to transcend average. 

More importantly, they decide to do so each day.