“The Great Gatsby” turned 100 this week. Probably, like me, you first read it in high school. My true engagement with the novel, though, began five years ago, when I was in my 50s and a writer and college teacher, and I started listening to a portion of the “Gatsby” audiobook every night.
I started on March 17, 2020, which was the day the province of Ontario, where I live, declared a state of emergency because of Covid. My wife and I had listened to Jake Gyllenhaal’s rendition of “Gatsby” during a 2015 road trip, liked it and thought it would be a diverting bedtime story to get us through the lockdown, which we expected to last about three or four weeks. We set a sleep timer, pressed “play” and listened for 45 minutes, and the lockdown wound up lasting nearly two years.
“Gatsby” for me has grown from a novel bedtime story to a nightly ritual to a kind of compulsion. It’s hard for us to imagine going to bed now without the compelling timbre of Mr. Gyllenhaal in our ears. In 2023 alone, I listened to “Gatsby,” which runs in its entirety for 289 minutes, just over 48 times. I broke that record in 2024 when I stopped setting the sleep timer and began listening to the entire book overnight, letting it unspool into my ears while I slept. “Gatsby” has now laid down roots in my brain — even into my dreams. In a way, that’s not just true of me but of the entire culture.
The literary critic Maureen Corrigan once wrote that “Gatsby” contains some of “the most beautiful sentences ever written about America,” and it persists as a book that is nearly “perfect despite the fact that it goes against every expectation of what a Great American Novel should be.”
Not only has it inspired at least five movies, an opera and a Broadway musical, “Gatsby” also has a habit of popping up in the strangest places: When the comedian Andy Kaufman wanted to subvert his stand-up by reading from a novel onstage, including on an episode of “Saturday Night Live,” he chose to read from “The Great Gatsby.” His prank inspired the New York-based experimental theater company Elevator Repair Service to create “Gatz” in 2004, a six-and-a-half-hour performance that involves actors reciting the entire book, word for word. And, yes, I’ve seen “Gatz.” Twice.
There is a certain look I get when I tell people about my “Gatsby” ritual — call it “curious concern.” If I explain that during Covid I started listening to “Gatsby” as a comfort before bed — and have been listening to it almost every night since — I can hear how strange these words sound even as they trip out of my mouth. Who chooses as a ritual bedtime story a bittersweet novel that ends with a murder-suicide (preceded by a fatal car crash) in which no one finds love and the only character who ends up close to happy is a violent racist and a serial cheat? Maybe “Pride and Prejudice” would be a more acceptable obsession. It’s also a masterpiece and it has a happy ending. But only “Gatsby” can hold my attention. By now, I’m steeped in it.
For all this, I am not close to being an F. Scott Fitzgerald scholar. If you had to stick me with a title it would be “Fitzgerald Weirdo.” But I do know this: for a 100-year-old novel written by a 28-year-old, “Gatsby” ages remarkably well.
When I first read it as a teenager, I saw myself in Jay Gatsby, with his grand aspirations, mysteriousness and romantic frustrations. Throughout my 20s, I found new meaning in its examination of ambition and reinvention, and by the time I got to my 30s, I was convinced I was Nick, an observer of life “simultaneously enchanted and repelled.”
Now, in my 50s, I’ve come to realize that, if anything, I’m “Owl Eyes,” the minor character who lurks about on the sidelines and admires Gatsby’s library, looking through the bookshelves while throwing around words like “ascertain.” The Owl Eyes in me wants to tell all the characters just to enjoy themselves more, and I’m particularly annoyed at Nick for blowing his relationship with Jordan. I get it: When you’re young, the fact that Jordan is “incurably dishonest” and deals in subterfuges to “satisfy the demands of her hard, jaunty body” may feel like a problem. By your 50s, it’s more like, “Hey, nobody’s perfect.”
In his 1934 essay “Sleeping and Waking,” Fitzgerald, a famous alcoholic and occasional insomniac, observed that insomnia arrives when “seven precious hours of sleep suddenly break in two. There is, if one is lucky, the ‘first sweet sleep of night’ and the last deep sleep of morning, but between the two appears a sinister, ever widening interval.”
When I am stuck in such a widening interval, I turn to “Gatsby.” Listening in the dark with my eyes closed, nothing obstructs Fitzgerald’s prose. I cannot skip a word or line; each one plays into the other, and I lay in bed like a spellbound child who has heard his favorite story a thousand times.
One night last summer, I fell asleep to “Gatsby” and dreamed I was at my uncle’s sparsely attended funeral. My uncle was a self-made man; we had grown close, and I came to think of him like an older brother. He was someone I admired and relied on. He died by suicide in 1991, and it changed my life forever — just as, in a way, Nick’s life changed after Gatsby’s death. Like Nick, I “closed out my interest in the abortive sorrows and short-winded elations of men.”
After 50,000 minutes, the novel has become many things to me: an epic poem, a hard-boiled chivalric fable, a tale in which all the heroic and extraordinary deeds seem modern for being ironic, including the lesson that greatness lies in the past — beginning with the “vanished trees” that “made way for Gatsby’s house” — yet all the heroic efforts to recapture it are doomed. “Gatsby” is populated by people driven, to one extent or another, by dreams of what they have lost or what they have never found, and I relate to that. “Waste and horror,” as Fitzgerald once wrote; “What I might have been and done that is lost, spent, gone, dissipated, unrecapturable. I could have acted thus, refrained from this, been bold where I was timid, cautious where I was rash.”
When will I stop listening? Not any time soon. Listening to “Gatsby” for five years has allowed me to feel that I have come to know Fitzgerald better, and myself, too. Besides, even after 100 years and 200 listens, I don’t want to say goodbye. None of us do.
Andrew Clark writes a weekly column for The Globe and Mail and is the coordinator of the comedy writing and performance program at Humber Polytechnic in Toronto.
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