Swift’s Homage to Gatsby

Osama Alkhawaja
6 min readApr 25, 2022


Back in our more vulnerable years — when we thought a few months of Covid was all we had to endure — Taylor Swift released Folklore. I was studying for the bar exam at the time, and I was not a Taylor fan by any means; Folklore changed that a bit (I denouce her prior work and I reserve judgement on any furture production). Cliché as it sounds, I listened to the album on repeat as I biked by the lake near my house. I also happened to be reading The Great Gatsby for the first time (blame my high school lit teacher for that).

So in the absence of human interaction, I figured I’d go on a little rant exploring these two bodies of work.

At its core, Gatsby is the account of a man who can’t get over a summer fling. After falling in love with Daisy Buchanan, Gatsby convinced himself that he had neither the wealth nor social status to marry her. He then manufactured a persona with the singular goal of becoming worthy of the woman he loved. Unable to move on from the past, he crafted an imagine of a man he dreamt of as a child to court a woman who only ever exisited in in his mind’s eye. So became the Great Gatsby. But despite his new found money and charm, he ultimately fails to win Daisy back. On the surface, he was thwarted by the social stratifications of the Gilded Age: new money remained new money. But on a deeper level, it was Gatsby’s self imposed barriers that limited his ability to be with Daisy. Gatsby’s story epitomizes what it means to have the right to pursue but not obtain happiness.

As I hear it, Folklore’s opening track sets the groundwork for the album-long extended metaphor to Gatsby’s story. The 1 is written from the perspective of someone who can’t help but reflect on what could have been if the relationship in question had gone a different path. In the iconic chorus, Taylor likens her failed relationship to the spirit of the 1920s: But we were something, don’t you think so? Roaring 20’s throwing pennies in the pool. An obvious double entendre, the Roaring 20’s refers to the Gatsby decade and the defining years between youth and adulthood.

As Taylor and Gatsby both know all too well (i couldn’t help it), those who find themselves on the other side of thirty and alone easily slip into the trap of being consumed by what could-have-happened. Taylor reflects, in a moment of great vulnerability, that if her wishes came true. It would’ve been you. For Taylor, this statement is an emotional and mental counterfactual. But for Gatsby, it was the driving force of his actions. Gatsby could not, resist the temptation to ask … If one thing had been different. Would everything be different today?

Nick Carraway, the novel’s unreliable narrator, warned Gatsby that he shouldn’t ask too much of his former lover. He explicitly told Gatsby that he “can’t repeat the past,” to which Gatsby retorts: “Can’t repeat the past? . . . “Why of course you can!” This reflects both Gatsby’s greatest strength and weakness. He was so sure of the future, but only because he remained fixated on the past. Despite the catastrophic events that spring from Gatsby’s attempts to win Daisy back, we never hear Gatsby express an ounce of guilt. Gatsby had no defense for never leaving well enough alone. Up until the end, in the gardens outside Daisy’s home, he insisted that all was going according to plan.

And because Gatsby was living outside the present momemnt, he could not see Daisy for who she really was, or at least, who she became: a careless person reckless with the emotions of others. She once remarked that the best thing a girl can be in this world is “a beautiful little fool.” This let us into Daisy’s secret: she was not the fool she was pretending to be; she could recognize the lack of meaning and purpose in her shallow life, and she was content with it. For Daisy, it would’ve been fun if Gatsby had been the one. But that’s all she was ever after. Fun. Whereas Gatsby was foolishly committed to their love, Daisy was only playing the part.

This theme comes to head in The Last Great American Dynasty. This song is dedicated to the life and times of Rebekah Karness, a woman who married the heir of the Standard Oil fortune. After her husband’s death, Rebekah instantly became one of the one wealthiest people in America. She would have fit right into West Egg with all the other uppity social climbers. A real-life rendition of Gatsby, Rebekah spent fortunes throwing lavish parties and glamorous events just to be snubbed by the gatekeepers of social capital. She ultimately died alone after a series of unsuccessful marriages.

Rebekah and Gatsby’s stories capture the spirit of the Roaring 20’s, particularly the plight of young ambitious people who had a marvelous time ruining everything. Despite the massive upheavals that occurred during the 1920s, their stories reflect how inelastic social stratification remained. One wonders if Rebekah’s life, like Gatsby, mirrored a character of herself that she invented as a child. If so, Rebekah also believed in Gatsby’s green light. A future we pursue relentlessly even as it seems to recede before us, on the faith that we will reach it one day. This belief resulted in tragic outcomes for both our protagonists, who seemed to be chasing the one thing they could never get, after all, There’s only so far new money goes.

And then there’s the three-song love triangle between Betty, James, and Augustine. Betty’s reference to a party serves as the emotional and lyrical bridge to Gatsby. As James drifts by Betty’s house on his skateboard, and Gatsby gazes at Daisy’s green light over the harbor, both men are paralyzed by the prospects of coming face to face with their former lovers. Like Gatsby, James is desperately trying to overcome events in the past. Particularly his own infidelity. If it were up to James, the summer with Augustine would never have occurred. Meanwhile, Gatsby wants to recreate the past. In short, James regrets the past, while Gatsby lives in it.

Despite these differences, both Betty and Gatsby build up to the moment when the former lovers finally meet at each other’s homes. When James arrives at Betty’s door, it sinks in that he will no longer be able to recreate this moment in his head after it occurs. Because Betty will either tell James to go to hell, or will she invite him to her garden. From then on out, reality, for better or worse, will replace his dreams. When Gatsby was waiting at Nick’s house for Daisy, the same thoughts and fears must have been occupying his mind.

Sadly, reality could not compete with their dreams. Nick realized this as an outsider looking in. He lamented that, “[t]here must have been moments even that afternoon when Daisy tumbled short of his dreams — not through her own fault, but because of the colossal vitality of his illusion. It had gone beyond her, beyond everything . . . No amount of fire or freshness can challenge what a man will store up in his ghostly heart.” Nick understood that Daisy and Betty could never live up to the expectations Gatsby and James had for them. Yet, despite these fears, and the inevitable shortcomings of reality, James and Gatsby both beat on against the current. An encouraging thought.

The best piece of art functions as a mirror, and Folklore and Gatsby both share this quality. A century apart the lessons remain the same. Both bodies of work are likely to endure­–despite their hyper specificity and deeply contextualized narratives–because there is enough ambiguity in the characters to enable us to use them as barometers for measuring our own life. Whether Taylor meant to or not, to me, Folklore will always be an unofficial homage to The Great Gatsby.



Osama Alkhawaja

Lawyer writing on politics, history, and anything that interests me in at the moment