The Ever-changing Great Gatsby

My kid recently told me he is reading The Great Gatsby in English class. I beamed a broad smile. This is one of my favorite books, what I like to call the ever-changing Great American Novel. Yet, at times, I wonder if we do a disservice for putting this book on high school lists. For a trick question, what is the primary theme?

Maybe the story shows our dreams lead to despair. But isn’t that a worse tragedy if we don’t dream big enough? I think that’s what makes this book beautiful. Because each word is painfully constructed with a caring and longing that is hard to imagine in today’s abundance of mechanical work, a machine could never write this. With all the talk of recent AI removing the writer, I go back to Gatsby. Like the rich in the story, our ability to write on a whim and move on, a volume game, maliciously destroys the written word. Our society often takes language for granted and then grasps at straws when we need it most.

In flipping through Gatsby’s pages again, I do know a tortured soul wrote a beautiful book with flawed characters. His technique still gives me pause. It’s a work of constraints as Fitzgerald used the first person narrator unlike anyone else. I know there are many great books written in this style. Hundreds. Thousands. More so. But I think this is unique because the perspective doesn’t lie with the main character.

There are no true heroes in this story. But Gatsby is the gravitas of the novel. By being told through an outsider’s lens (Nick Carraway), Gatsby is elevated into a larger-than-life mythical figure, hides some of the seedier elements, and makes the telling soar. There is a reason this is on my kid’s high school reading list. Why wouldn’t it be?

I love critics. Take the music industry, they can go on for hours debating Dylan, U2, Taylor Swift, etc., My favorite line is, Did you really hear the music? And damn it, I say, You bet I heard it!

But when I look back, I have to wonder, as it relates to Gatsby, did I really read it? Did I understand?

List the themes abundant. Class. Race. Money. Power. Never giving up. Pushing onward. Hope. Moral failings. Awful people—they do exist. If you haven’t picked up Fitzgerald since high school, you’re doing yourself a disservice. In our age of abundance, we don’t think about the sheer beauty of a novel. And how hard they are to create. But what makes this a quintessential work is each time I dare flip through the pages, it feels new. Yes, I look at the characters differently or discover a new theme or favorite quote. Few books have this power. Because of its chameleon-like nature, I wonder if that’s the reason the movie retellings are often panned. There are four; one is lost to time. When Fitzgerald watched the original, he supposedly hated it. They didn’t really read the words, did they?

What’s sad is this wasn’t a commercially successful book. It sold less than 21,000 copies. The author died at age 44, poor and down on his luck. Did he see the opus from multiple points of view? Finishing at age 29, did he even appreciate what he had accomplished? Yes, luck lurks with any creative endeavor. A necessary part of the process.

But I believe magic exists too.

You see, I love older typewriters. When you press on any of the keys, a pop sounds against the paper. Not a bam. It’s hard to describe unless one sees a mechanized beast in action. A swoosh, smack, and then recoil. Repeat.

I have an Underwood 5 sitting in my office. It’s a not-so-subtle reminder to write. Many remain in old workshops and garages, but fewer in working conditions as the days pass. But to make the sound, engineering magic happens. Upon finger push, a mechanical hammer extends down on an ink ribbon, which in turn presses onto the paper. And that’s just for the arm. That doesn’t consider the shift in the feeder, the whirl of the gears, and the ringing bell when the return key is hammered.

Although Fitzgerald wrote in longhand, someone had to type out his work. At shy of 50,000 words, that’s an immense number of smacks on the keyboard. The engineering required to create Gatsby, or any book, is truly revolutionary.

Take the following, “In his blue gardens men and girls came and went like moths among the whisperings and the champagne and the stars.” I wish I could will a sentence like this into existence. In the most recent telling of Gatsby, the movie depicts the storyteller using a Remington Vs. Underwood, but is long hand the true means to belt out a novel? And if I torturously wrote in longhand, would it make me a better writer?

I once worked at a company that prized the Dvorak keyboard layout. The CEO wanted anyone on a Mac to change out their keys in the settings menu. To my former colleague’s credit, it is more efficient. Studies give it four to five percent, which is huge if you’re making code or belting out a thousand plus words each day.

But this is at typing. What about the larger pie?

When the Underwood 5 launched, the QWERTY layout was standard, which is sometimes maligned today. I love Twitter. If you type in QWERTY, it’s easy to find the hate on why a lost generation built something so inefficient. The haters often roll along with some pithy about these people not thinking correctly. After all, only Big Tech can save the world. I can jest here.

The challenge with this line of logic is people often overlook the entire system. Putting on my late 1800s hat, list the constraints. Paper. People. Ink. By extending the supply chain, QWERTY becomes an achievement. If you slow the typist down by that same four to five percent, the life of the interior mechanics extend. Things don’t break. Typing goes on.

Also, the keys are in certain places for a reason. Think of the movie Ghostbusters. Never cross the streams. Well, never cross the keys. If you tried to map an efficient layout on an UnderWood or Remington, the hammers would crash into one another.

And old keyboards still work. In the year 2023 (I do miss you, Conan O’Brien), my Underwood still types. My current keyboard of choice might make a decade. But a century?

What have you learned? Well, old typewriters were built to last. Great American Novels too—don’t cheapen them. How they are written does indeed matter. And if you haven’t picked up Gatsby since your Junior year of high school, do yourself a favor. Go buy the book or visit your local library.


  • Gatsby. 1925 Edition.
  • The picture is the Underwood 5 that sits in my office. Where did I find this? That’s what I love about the internet. One can find anything. Random antique shops help. Research too. There are many in the wild, but the condition is key. After years of looking, I finally found one on Etsy—it’s better than the everything store for obscure typewriters. What was better is that the seller repairs these for a living, shipping all over the world. Instead of paying crazy shipping costs, I met him at a gas station. We exchanged pleasantries. And I’ve been admiring it each day since as I type away, trying to create the next great novel. And, yes, I know I doubt it’ll top Fitzgerald. Can anyone? That age is gone, lost in favor of technical fortitude.