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  • Katherine Dahl

The Great Gatsby: A Jazz Age Classic in Four Songs


Leonardo DiCaprio as Gatsby in The Great Gatsby (2013)

Whether you read it for school or just to see what the hype was about, anyone who remembers The Great Gatsby knows it is one of the most interesting classics of the roaring ‘20s. For those unfamiliar, the story—told through the eyes of the Westerner, Nick Carraway—focuses on the mysterious and illustrious East Coast millionaire, Jay Gatsby. Gatsby, who quickly becomes an object of Nick’s fascination, hosts lavish parties in his mansion, owns a flashy car, and has countless connections in the city. As Nick eventually finds out, this is all an attempt for Gatsby to recapture the attention of his old lover, Daisy Buchanan, who herself has married another man. Gatsby’s idolization and obsession with their past romance leads him to entangle himself (and Nick) into the lives of the Buchanans, no matter the negative consequences.


Billie Holiday's 1957 self-named album

For five years, Gatsby maintained a zealous love for the young, beautiful Daisy, even after she married Tom. He rebuilds his entire life and builds up his fortune to impress her when they finally meet again. In the novel, Fitzgerald uses the moon as a symbol for Gatsby’s vision of the young Daisy; thus, “when [Gatsby is] looking at the moon,” he’ll actually “be seeing Daisy," like in Billie Holiday’s “I’ll Be Seeing You." Gatsby actually projects Daisy into almost everything he sees, like flowers (obviously) and the green light across from the lakeshore on the Buchanans’ dock. He sees her in “all the old familiar places” and in “everything that’s light and gay,” since Daisy was and continues to be his sole motivation for continuing on.


The Platters' Golden Hits compilation featuring "The Great Pretender" (1986)

Gatsby became a brand new person over the course of those five years—he became a party man, an extravagant character, and the subject of much gossip among the neighbors, even though no one really knows much about him. He adopts the “great” persona to completely erase his poor past and lowly upbringing. Thus, he becomes “The Great Pretender,” just as in the song of the same title by the Platters. He is immensely popular, so when “[he’s] lonely," “no one can tell” because of how he hides behind his flamboyant personality and glittering reputation. The people who attend his parties don’t know about his yearning for Daisy and, therefore, don’t know about his past nor his present. The ‘Great Gatsby’ is a mask for the real Gatsby, who, despite his endless amounts of material possessions, riches, and friends, is eventually disillusioned with the new life he leads.


Gatsby, Daisy, Nick, and Tom (left to right) at a lavish Gatsby party (2013)

When Daisy does come back into that life, Gatsby realizes he needs to overcome her attachment to her husband, Tom Buchanan. He hopes his new wealth and status will dazzle her into rekindling their old love outside of her marriage. In the same way as in “This Boy” by the Beatles, Gatsby “wants [her] back again” away from “that boy [who] took [his] love away." Tom is himself a racist, domineering, and unfaithful husband who “isn’t good for Daisy,", even if her life with him is comfortable. Gatsby’s entire persona and life were built around the hope that it would win her back, and the crux of the novel comes from Daisy’s conflicting feelings for Gatsby versus for Tom. Poor Nick is stuck in the middle of it all. Daisy is his cousin, but Gatsby is his friend.



Lonesome Dreams by Lord Huron (2012)

The novel is the written account Nick wrote after moving away from the coast. The conclusion of the story has Nick moving “way out West” even if his heart is left in the East with Gatsby (and Daisy, to some extent); thus, the final song, focusing on Nick now, is “I Will Be Back One Day” by Lord Huron. The “great big lake” in the song is reminiscent of the cove by which Nick and Gatsby lived, and it was indeed the first place Nick saw Gatsby. Even years and years after the conclusion of the story, Nick still remembers Gatsby with a sort of mystified fondness: he “can’t seem to leave it behind," which is why he chose to write about his experience in the first place. He’s stuck on those “windswept shores of the time before," so he immortalizes them into the pages that we read.


Gatsby and Daisy (the Great Gatsby 1974)

I read The Great Gatsby nearly a year ago, and I still remember it clearly. I think I’m stuck in the story as much as Nick is. It’s short and sweet and perfectly poetic—one of my favorite modern classics, if that's a bit basic for me to say. If anyone wants to get into classics, this is an easy start. The movies are great, too! In some cases, they’re called classics for a reason. I hope everyone had a great Thanksgiving break!


Runner-ups: “Don’t Let Him Go” by REO Speedwagon, “Money Honey” by Elvis Presley.


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