O’ Henry Revisited
’Is O. Henry still relevant today?’ It’s a question that three friends — I the youngest by nearly two decades, they the seasoned veterans — decided to test during the strange stillness of Covid. On May 1st, 2021, we set ourselves a rather reckless mission: to reread every word O. Henry ever wrote, slowly, deliberately, over the course of a year. And we did. What follows are the reflections and reviews born from that long, unusual experiment — an O. Henry revisited, re-examined, and re-imagined for a modern age.
There’s something deliciously ironic about reading ‘The Four Million’ in the middle of a world-altering pandemic, when the idea of a “city of millions” felt like a fever dream and the idea of interacting with even four humans in a single day felt like some dangerous, prelapsarian luxury.
The book — or rather, the constellation of stories bundled inside it — becomes a counterpoint to the global loneliness of Covid. O. Henry’s New York is everything lockdown life was not: loud, crowded, unpredictable, brimming with accidental contact, nuisance encounters, overheard conversations, and the constant threat of bumping into someone who might entirely reconfigure your day, your life, or your emotional circuitry.
And rereading it now, you can’t help but notice how deeply he loved the city not for its grandeur but for its chaos, its pettiness, its tiny, tender miscalculations. He wasn’t a writer of skylines; he was a writer of street corners. And in a pandemic-era rereading, those street corners begin to glow strangely — like abandoned stages waiting for actors who never showed up.
That urban hum we all missed so badly becomes the invisible subtext. O. Henry’s New York suddenly becomes mythical, a place we might have dreamt during lockdown as we wandered our own apartments like cranky ghosts.
The title itself, ‘The Four Million’, has a kind of mathematical swagger to it — a flex aimed at a visiting snob who’d dismissed New Yorkers as aesthetically uninteresting unless they belonged to the top four hundred elite. O. Henry, in full chaotic-good mode, slaps back with the thesis that every single one of those four million souls has a story worth listening to. And reading it post-2020, when the world finally admitted that “essential workers” were not who we thought they were, his democratic tenderness feels prophetic. He saw beauty, drama, comedy, and absurdity in people long before the world learned to value the unnoticed.
There’s a particular intimacy in the way he moves through these stories — as though he’s walking down a Manhattan street with a psychic mic, picking up every faint emotional frequency. He doesn’t lean into the grandeur of city life; he leans into the micro-emotions, the incidental heartbreaks, the impulsive joys. His tone is always tinkering between mischief and melancholy. And that’s where the postmodern rereading kicks in: O. Henry’s stories are always built on the assumption that reality is unreliable, that chance is an author in its own right, and that the universe has a dark sense of humour.
Covid stripped us to our private narratives; O. Henry reminds us that stories are fundamentally communal. His city is alive with entanglements. You get the sense that any two people in his universe could have collided and generated a tale. It’s a vision completely at odds with the isolated, sterilised, hyper-sanitised world we lived through.
And so reading it now, the collection becomes almost utopian — chaotic kindness, unpredictable connections, emotional generosity erupting in alleyways. Even the con artists in O. Henry’s world have softer hearts and cleaner consciences than many real-life people we encountered online during lockdown.
The postmodern lens also draws out the meta-layer O. Henry himself may or may not have intended: the stories within ‘The Four Million’ often function like tiny parables about perception, class, desire, and the questionable reliability of appearances. Every character misreads someone or something. Every assumption gets gently overturned. If the modern meme culture had existed in O. Henry’s time, he would’ve been the undisputed king of the “plot twist” template — a twist not meant to shock, but to recalibrate the reader’s moral coordinates.
And while the pandemic made us all hyper-aware of inequality — who gets to stay home, who gets to risk their life for someone else’s groceries — O. Henry was always obsessed with the fragile social ecologies of the city. The clerk, the waitress, the quiet lover, the petty thief, the lonely wanderer: he elevates them not by idealizing them but by showing how complicated their inner worlds are. His stories function like tiny empathy machines. And rereading them during a time when empathy itself felt endangered gives them a new emotional voltage, almost like they were written for the future rather than the past.
There’s also the way he handles time: everything in his stories happens quickly, impulsively, and sometimes absurdly. Characters fall in love, fall out of love, lose fortunes, gain revelations, or stumble into chaotic morality plays within the space of a few pages. Covid time, by contrast, was glacial and muddy. Days lost shape. Hours bled into one another.
So O. Henry’s pacing feels like the opposite of our pandemic brain fog. It feels electric. It feels caffeinated. It feels like stepping out of a long dream into a city that’s fully awake.
But beneath the quickness, there’s a dreaminess — a strange emotional thickness that becomes clearer when viewed through the rearview mirror of 2020–2021. The stories are light, yes, but they shimmer with little aches. A humor that wobbles between mischief and sorrow. An optimism constantly negotiating with disappointment. A sentimentality that keeps wandering dangerously close to cynicism but always pulls back at the last second, as though O. Henry can’t help but believe in people even when they behave like gremlins.
This emotional tonal shift feels especially resonant for those of us who carried tiny heartbreaks through the pandemic — the friendships that fizzled, the people who changed, the versions of ourselves we shed. O. Henry’s characters are always in transition. They are caught between what they want to be and what the world lets them be. They’re improvising their way through life, attempting to manufacture dignity out of chaos. Their desires are small but fierce. Their mistakes are human. Their victories are absurdly fragile.
And yet, O. Henry never laughs ‘at’ them. He laughs ‘with’ them, from a place of affection. The world may be cruel, but its people — in his vision — are redeemable through small acts, odd coincidences, and unexpected moments of grace. And perhaps that’s why the collection feels so comforting today. It reaffirms the idea that the world is not driven purely by power or cruelty. It suggests that the universe still makes room for accidental kindness, secret generosity, impulsive sacrifice.
In a postmodern read, ‘The Four Million’ begins to look like a patchwork novel — a distributed emotional network, where each story feeds into a larger narrative about the city’s collective psyche. O. Henry gives us a metropolis not made of stone and steel but of desire, disappointment, longing, and chance. His New York becomes a character — one with too many moods, too many contradictions, too many pockets of strangeness to fully map. It has the kind of interiority a good novel has, except its consciousness is scattered across four million minds.
And that’s the strangest and loveliest part of reading it now: the recognition that the pandemic briefly turned all of us into isolated protagonists of our own little O. Henry stories — improvising, yearning, stumbling through the plot-twists of circumstance. In his world, endings are rarely neat, but always meaningful. And in ours, pandemic endings weren’t neat either — but they pushed us toward a deeper understanding of how we occupy the world and how the world occupies us.
O. Henry’s gentle anarchism — the belief that even the smallest life is worth a story — feels like the antidote to modern cynicism. He democratizes narrative importance. No character is too insignificant for a miracle, a revelation, a moral recalibration. And post-2020, when so many people felt invisible or reduced to statistics, his vision feels like a rebellion against erasure. It insists that every human life is thick with possibility.
And so ‘The Four Million’ becomes the literary equivalent of wandering through a crowd with an open heart, listening, observing, wondering. It’s a celebration of the unnoticed, the ordinary, the chaotic little tragedies and tender absurdities that make up a shared urban life. And though the stories are anchored in an older New York, the emotional architecture is timeless. People still hope this way. Still break this way. Still misread signals this way. Still love each other in these tiny, impulsive, catastrophic ways.
Which leads us perfectly to the final thought.
What could the ending have been like?
In an alternate universe — one where O. Henry leaned harder into sentiment — the final pulse of the collection might have crystallized into a single story that tied its threads together, giving all four million souls a symbolic moment of convergence. Or the ending could have stepped into a grander moral arc, letting a final tale deliver a quiet verdict on the unpredictability of human decency.
Another path might have leaned into playfulness: a meta-ending where O. Henry steps into his own narrative, cheekily admitting that he, too, is only one of the “four million” and therefore no more omniscient than the reader. Or the book could have ended on a darker, more modern note — emphasizing the alienation that lurks beneath the bustling city.
But the most intriguing alternate ending would be one that reveals the connective tissue between the stories — a single event or encounter that exposes how deeply the characters’ lives brush against each other without ever realizing it. A web we only see at the final moment.
Yet O. Henry chooses neither neat closure nor overt spectacle. His real ending is a soft pulse, a democratic assertion, a gentle insistence that the city is its own story — unfinished, unwieldy, and full of people whose lives matter even when no one is watching.