This Is The Greatest Novel Ever (And Why I Keep Re-Reading It)

It changed my life.

I don’t mean that the way some writers might. Yes, it is one of the best and most beautiful novels in the English language.

But The Great Gatsby first changed my life not by reading it, but by writing about it.

In 2004, my 11th-grade English teacher assigned us an essay. The prompt was: “Analyze how and why The Great Gatsby is an exploration of the American Dream as it exists in a corrupt period.” I thought I was completing just another ordinary assignment. But the next day, Mrs. Kars printed out my essay and we spent the entire period reviewing it with the class.

It was the first time anything I had ever written had been recognized. Now that I think about it, it may have been one of the first times in my life that I had ever felt like I might be anything but average. I would later ask Mrs. Kars for a letter of recommendation to a college I did not get accepted to, but I can still remember a line from it. “I have no doubt,” she said, “that Ryan will someday be a literary giant.”

I don’t know about that, but again, that was the first time I recall anyone truly believing in me. It’s an incredible gift to give someone that—a good teacher can be an angel in your life. She was that for me.

Anyway, as I look at that essay now, I do see a flicker of the writer I would later become but mostly, I see the beginning of my fascination with the themes of that novel. Just last month, I read from cover to cover this incredible annotated 100th-anniversary edition of The Great Gatsby, and I found myself thinking again about what this book means and why it has endured now for over a century.

A few years ago I was on the Jim Rome show (which is surreal since I used to listen to him in the afternoons after high school right around when I read Gatsby), and he mentioned that one of his college professors claimed that The Great Gatsby is “a perfect novel.” Of course, no art is perfect but I think we can say it approaches perfection and is without question a work of genius. By “genius,” I have in mind F. Scott Fitzgerald’s definition: “Genius is the ability to put into effect what is in your mind. There’s no other definition of it.”

In July 1922, as he first began to imagine the novel that would become The Great Gatsby, Fitzgerald wrote to his editor Maxwell Perkins, “I want to write something new—something extraordinary and beautiful and simple + intricately patterned.” The Great Gatsby may not be flawless, but it so precisely accomplishes what it set out to do. It put into effect exactly what was in the author’s mind. It is extraordinary and beautiful and simple and intricately patterned—deceptively simple on the surface, endlessly rich underneath.

And by the way, there’s a lesson in that, too. Because putting into effect what was in his mind didn’t come easy. Sometimes at Maxwell Perkins’s urging, and other times out of his own exacting standards, Fitzgerald subjected Gatsbyto a long, painstaking revision process. In April 1924, he wrote to Perkins to explain he’d thought of a “new angle” for the novel, and therefore, “I’ve had to discard a lot of it—in one case, 18,000 words.” And he was still struggling with the title. Would it be Gold-hatted Gatsby? Trimalchio in West Egg? Trimalchio? On the Road to West Egg? The High-bouncing Lover? A month later, Fitzgerald reported that “the novel is going fine — it ought to be done in a month,” but on second thought, “I’m not sure as I’m contemplating another 16,000 words.” Finally, on October 27, 1924: “Dear Max…I’m sending you my third novel: The Great Gatsby. I think that at last I’ve done something really my own, but how good ‘my own’ is remains to be seen.”

By then—after all the revisions, rewrites, and discarded words—Perkins was convinced. “I think the novel is a wonder,” he wrote to Fitzgerald. “The amount of meaning you get into a sentence, the dimensions and intensity of the impression you make a paragraph carry, are most extraordinary. The manuscript is full of phrases which make a scene blaze with life.”

The reader, I think, feels the layers, the dimensions, the amount of meaning beneath every sentence. As with any great piece of art, every time I revisit it, I see something I hadn’t seen before.

I still have that copy from that 11th-grade English class. I can see the food I spilled while I read it at the kitchen table of my parent’s house or as I threw myself over the arm of the couch in the living room as teenagers like to do. I can see my handwriting in the margins.

My copy of The Great Gatsby from high school.

I can also see the things I noted when I re-read it in college. I can see the notes I took when I read it in my twenties. I can see how I barely noticed the scene on page 73 the first few times I read it, when I went looking for it in 2016.

At the time, reading Eisenhower’s memoir, At Ease, I was struck by a passage about how the young lieutenant colonel had eagerly followed the 1919 World Series as the scores came in via telegram—and, like everyone else, suspected nothing. Years later, he’d say the revelation of the Black Sox conspiracy profoundly changed his view of the world—it taught him never to trust first appearances. “I grew increasingly cautious,” Eisenhower said, “about making judgments based solely on reports…Unless circumstances and responsibility demanded an instant judgment, I learned to reserve mine until the last proper moment. This was not always popular.”

Suddenly, I remembered there was something about the 1919 World Series in that book from high school. I found my copy and then that scene on page 73. It’s the one where Jay Gatsby introduces Nick Carraway to Meyer Wolfsheim, casually mentioning that he’s the man who fixed the 1919 World Series. The idea staggers Gatsby’s idealistic young friend. Of course, Carraway knew the series had been thrown. But “if I had thought of it at all,” he says, “I would have thought of it as a thing that merely happened, the end of some inevitable chain.” It was unbelievable to him then, as it is to us now, that one person could have changed the outcome of an event watched by some fifty million people. And it hit me at that moment as the perfect opening of the book I was writing about Peter Thiel’s secret lawsuit, the book that would become Conspiracy.

In my twenties, when I worked at American Apparel, I had my first encounter with a Gatsby-esque figure in real life. The founder Dov Charney—one of these hyper-successful entrepreneurs but also a profoundly flawed individual—seemed like he’d stepped right out of a Fitzgerald novel. Dov was chasing something, trying to impress someone, trying to prove something. As a Canadian, he had an almost painfully urgent belief in the American dream, in building something. It was also clear to me that the “American Apparel girl” which became a sort of fashion icon, was for Dov, someone or some type of girl from his youth that he was desperately, desperately trying to get back to. It was, like in the book, a cartoonish pursuit of success and fantasy—all the while thinking, When I get there, I’ll feel good, I’ll be happy, I’ll be respected, I’ll be loved. But, of course, you never actually get there. You’re like Gatsby chasing after the green light. You never get it. And you forget…he ends up dead in his swimming pool and nobody comes to his funeral.

It is a tragic irony that Fitzgerald himself became a similar cautionary tale. As I said above, The Great Gatsby was initially subjected to extensive edits. Well, it was also poorly received when it was finally published. The reviews were mixed, the sales were underwhelming, and Fitzgerald—who thought he had written something extraordinary—was devastated by it all.

When I had Sarah Churchwell—an expert on 20th and 21st-century American literature and author of Careless People: Murder, Mayhem, and the Invention of The Great Gatsby—on The Daily Stoic podcast, she explained how the reception (or lack thereof) of Gatsby crushed Fitzgerald. “He pinned so much personal hope and ambition and desire and sense of his self-worth as an artist on Gatsby,” Churchwell told me. “And its comparative failure devastated him. And, in my view, it really precipitated his spiral…With Gatsby, he made this choice that he was going to write a masterpiece, and then it was met with bafflement. And he lost a lot of his self-confidence and a lot of his momentum at that point.”

Fitzgerald was dogged by the inability to practice what you have to learn as an artist (and a Stoic)—separating what part of the process is up to you and which isn’t. When Fitzgerald didn’t get what wasn’t in his control (critical reception, public praise) he had trouble coping. He began drinking more. He had trouble focusing. He chased pleasure and lived preposterously outside his means. This headspace makes it hard to live, much less write, and consequently, Fitzgerald would only finish one more complete novel after Gatsby. Like a great athlete who gets struck down in their prime, one of the greatest novelists of the 20th century left a lot of potential on the table. “The unfulfilled potential is heartbreaking,” Churchwell said. “It’s just absolutely heartbreaking.”

If you haven’t read The Crack-Up, you should. It’s a haunting book—published posthumously but written while Fitzgerald was falling apart. With a remarkable amount of self-awareness and humility, we see him wrestle in real time with his demons and flaws. It’s one of the most underrated books out there that every creative person should read.

As I was thinking about this very article, I took out my copy of Gatsby to revisit some of my favorite pages. I paused at those first few sentences that I’ve read dozens of times: “In my younger and more vulnerable years, my father gave me some advice that I’ve been turning over in my mind ever since. Wherever you feel like criticizing anyone, he told me, just remember that all people in this world haven’t had the advantages you’ve had.”

Those words have different meanings to me today than they did five years ago, let alone when I first read them at 15. Now I have kids, now I have a better sense of my own advantages in life, now I know how hard it is to write something that good without sounding preachy or lame.

I’m less judgmental of Fitzgerald and the characters in the book, too. I understand they were flawed people, doing the best they could. I am grateful to them for showing me lessons I now hopefully don’t have to learn the hard way.

And what’s true of that line is true of so many lines, so many scenes, so many other moments in Gatsby: each time you come back to them, they mean something different. Which, to me, is the mark of a truly great work of art, and the essence of why Gatsby has endured for a century and will still be read centuries from now.

The poet Heraclitus said, “no man ever steps in the same river twice, for it is not the same river and he is not the same man.” In the same way, if it is truly a great book, we never step in and out of its pages the same way twice.

I’ve stepped into the pages of The Great Gatsby many times since first doing so in Mrs. Kars’ class—at different stages of my life, in the middle of different projects, with different ambitions, different priorities, different definitions of success—and I’ve never been quite the same person stepping out of them.

And so, I need to make a revision—not a Fitzgeraldian 18,000-word rewrite, just a word or two.

I opened this piece saying, it changed my life.

More accurately:

It keeps changing my life.