Barry Lyndon and Jay Gatsby are two men from humble origins who dared to dream above their station. They changed their names, crafted new personas, and clawed their way into elite society. But in the end, both met tragic, almost inevitable, downfalls. Were their fates karmic? Deserved? Or were they simply victims of a cruel society?
At first glance, Barry Lyndon and The Great Gatsby are cautionary tales about the dangers of ambition and social climbing. But look deeper, their stories don’t just warn against greed; they ask what happens to a person who bases their entire selfhood on external validation. What if the ladder to success isn’t just hard to climb… but leads nowhere at all?
Jay Gatsby and Redmond Barry are both men possessed by a fantasy. Gatsby longs to be “old money”: to win back Daisy Buchanan and prove that he belongs among America’s aristocracy. Barry wants to be a British gentleman, a man of status, property, and legacy. For both, romantic love becomes a symbol of social acceptance, a stamp of legitimacy.
They chase this dream with everything they have: by changing their names, they shed their pasts. They perform their new selves with charisma, clothes, and curated mythologies. They accumulate wealth, by any means necessary.
But no matter how rich or refined they become, they are always seen as impostors. Gatsby as the flashy gangster; Barry as a gold digger that took his wife’s title. In both cases, money buys access, but never belonging.
What these stories reveal is simple but devastating: in their respective worlds, class is not about wealth, it’s about essence. It’s about lineage, manners, history, an ineffable legitimacy that cannot be bought, only inherited.
Both narratives expose the lie of meritocracy: “If you work hard enough, you can become anything.” Gatsby and Barry work hard, they even succeed by conventional standards. But they’re still doomed. Not because they lack effort or ambition, but because the social order is rigged.
Even worse, the pursuit itself becomes a form of self-erasure. In trying to become someone else, they lose touch with who they truly are. Their downfall is not just external rejection, but internal disintegration.
At the heart of both stories lies an existential crisis: What gives life meaning, is it love, status, success, or something more intrinsic?
Jay Gatsby dies clinging to his illusion, what Fitzgerald calls his “Platonic conception of himself.” His downfall is made all the more tragic by his genuine belief in the dream. Gatsby’s story is drenched in romantic melancholy. He believed the world could be remade by desire, and died never seeing the truth. Barry Lyndon, by contrast, never seems to believe in anything as deeply. Kubrick’s version of the character is colder, more cynical. An opportunist who grasps rather than dreams. And so, his end is not heartbreaking, but quietly forgotten.
Where Gatsby dies for a dream, Barry simply fades into irrelevance.
What makes these stories truly haunting is that no one escapes. Even the rich, even the Daisys and Lyndons of the world, are prisoners.
The poor are desperate imitators, always reaching. The rich are hollow gatekeepers of lineage, stuck in roles they never chose. Everyone performs. No one is free. In existential terms: the hierarchy itself is absurd. It demands that people act out scripts, wear masks, and deny their authentic selves… all in service of a social order that gives no real meaning, only status.
Daisy Buchanan isn’t a villain so much as a survivor. She chooses stability over romance, realism over Gatsby’s delusion. And who can blame her for that? Lady Lyndon, barely given agency in Kubrick’s adaptation, becomes a symbol of entrapment, passed from one cold, loveless marriage to another, reduced to a financial asset. They are birds in gilded cages, not queens of their castles.
Taking this into a modern frame, The Great Gatsby and Barry Lyndon are also cautionary tales for insecure men. Both Gatsby and Barry are consumed by the belief that they can fix something broken inside through external success. They are driven not just by ambition, but by deep emotional wounds:
“I’ll be happy once I’m rich… once I have her… once I belong.”
It’s a dangerous delusion, one that is still quite prevelant.
They measure their worth in money, women, and reputation, things that are inherently unstable. And so, when those things are threatened, their entire self-worth collapses. In this light, both stories become warnings for anyone chasing validation instead of healing.
True confidence doesn’t come from a mansion or a title; it comes from character. From Gatsby’s unwavering hope, and Barry’s love for his son, we had a few glimpses of the remaining authenticity in their lives.
In the end, Barry Lyndon and The Great Gatsby are not moralistic tales about how crime doesn’t pay or how ambition leads to downfall. Their message is deeper and darker. They’re existential tragedies disguised as social satires. They don’t just warn against wanting more in life; they warn against living through the eyes of others, against defining your identity through external recognition.
The society that these two characters were set in, 18th Century England and 1920s New York offered the promise that if you play the game well enough, you’ll win. But the game is rigged— worse, it is meaningless. The tragedy isn’t just that Gatsby and Barry fail, it’s that they believed success would save them. Their stories challenge us to ask: What are we chasing? Who are we performing for? And what happens when we fail to reach that dream? Because if your identity depends on others seeing you as worthy, then you never truly exist at all.
Gatsby and Barry live in eras where class is fate. Today, class is more like momentum: it’s possible to change direction, but it still shapes your speed and trajectory.And the existential core of their stories remains painfully modern: When you stake your self-worth on how others see you, even if you “succeed”, you may still end up empty.
So yes, today’s society might be more fair and more mobile. But the human condition: the longing to be seen, to belong, to feel like we matter, remains unchanged.
And when that desire gets outsourced to wealth, status, or admiration? The dream still kills.