When I used to teach The Great Gatsby, I spent the better part of a class period on the vehicles depicted in the first three chapters. My goal, of course, was to prepare the students for the climactic scene when Daisy Buchannan – at the wheel of Gatsby’s yellow car – kills her husband Tom’s mistress Myrtle Wilson shortly after a long, tense day in New York City. But even without this collision in mind, there is plenty to say in the early chapters in this novel about how its characters get from place to place. Tom’s mistress’s husband, for example, is a mechanic, and Tom stops to pick up Myrtle for a rendez-vous at her husband’s station, which couldn’t be any more torpid under a layer of gray ash that settled on it from the railyards on the edges of the city. When Nick Carraway meets Gatsby, Gatsby’s first remark is to give Nick an open invitation to come up with him in his hydroplane, and on the same evening, dozens of drunken partygoers bumble through the process of getting their stalled cars to start. And then there are all the emotions attached to cars – freedom, the thrill of spontaneity and recklessness and power, the tendency of a car to serve as a physical representation of its owner’s personality – and the fact that to drive a car is to wield a deadly weapon.

I don’t remember exactly when it was that I made the connection between all the conveyances in Gatsby and the even-more-impressive cache of vehicles owned by Christian Grey in the Fifty Shades of Grey trilogy. Grey’s collection is more impressive than Jay’s, of course, although he has the advantage of about 90 years on his Prohibition-era opponent. Grey’s collection includes several cars and SUV’s, plus a helicopter, a jet, a glider, and a yacht – and probably a few more that I am forgetting. This one perhaps-coincidental parallel between the two characters made me look for others, and each connection let to still others – and also, of course, to some areas in which the two fail to align with one another – which, of course, led to some interesting insights as well.

Both Jay Gatsby and Christian Grey were born into poverty in the north-central United States: Jay in South Dakota and Grey in Michigan. While Christian was adopted by an affluent family while still a child, both characters began to construct their adult selves through the help of mentors in early adulthood: Dan Cody in Gatsby’s case and Elena Lincoln in Christian’s. Both become impossibly, almost comically, wealthy – neither is ever depicted actually bathing in money Scrooge McDuck-style, but it’s a good bet they thought about it – but retain a hollowness inside them. Both are generally understood by the people who know them as lonely and sad. Both construct lavish homes for themselves. Gatsby becomes known for the extravagant parties he throws at his Long Island home – parties intended to lure Gatsby’s beloved, Daisy Buchannan, into the reunion that is Gatsby’s sole desire – and Christian’s home contains his “playroom” – a fully-equipped BDSM studio into which he brings, before the series opens, an ongoing series of petite, brown-haired submissive women who help him enact his fantasies. Gatsby gazes out over Long Island Sound at the green light he knows is attached to Daisy’s dock; Grey – who is always associated with aboveness: his penthouse apartment, his helicopter, his glider, his jet, his position at the apex of the economic ladder, the height differential between him and his submissives – fixes his gaze on Anastasia.

I know that many of my readers are probably screaming that this comparison makes no sense – how can I compare two works of such uneven literary merit? You’ll hear no disagreement from me on that front: The Great Gatsby represents the English language at its most graceful and inspired while the Fifty Shades series is barely written in complete sentences. Yet I’ll also argue that these works succeed equally at the goals they set out for themselves. Gatsby is meant as an examination of the American capacity for renewal, as both a celebration of its era (the 1920’s) and an exposé of the hollowness at that era’s core, and as a work of linguistic art; Fifty Shades is meant as a work of erotica aimed at a mass (though primarily female) audience. Evidence of Gatsby’s success is found in the fact that of all works of literature written in English, The Great Gatsby is the one that is taught as a core text in just about every American high school. I’ve never seen an American literature syllabus that leaves it out. Evidence of Fifty Shades’ success was palpable in the weird summer of 2012, when it was barely possible to eat in a restaurant or spend time in a crowded public place without hearing the series mentioned. Once that summer I was in line in the grocery store behind a grandmotherly white-haired lady who stopped to check her phone, which had beeped with a text message. “Oh, good!” she announced to half the store. “It’s the library! Fifty Shades of Grey is finally available! I’m going to go pick it up RIGHT NOW!” The same enthusiasm is ever-present today, one week after the movie adaptation premiered. I don’t think I’ve heard a single positive statement about the movie (which I haven’t seen), but still – the world (and by that I mean the internet) is abuzz about it.

Both novels are fairy tales, of course, and at least in part they are fairy tales about money. Both Jay and Grey acquire gigantic fortunes while still young, under dubious circumstances. Gatsby lost the fortune he inherited from Cody as easily as he gained it and soon amassed an even greater fortune on its own, in a manner Fitzgerald hints was likely illegal, involving gambling, the smuggling of illegal liquor, and/or other back-alley pursuits. Grey’s rise is even more shadowy and took place under the tutelage of Elena Lincoln, a friend of his mother’s who seduced him (and had sex with him, and made him her submissive) when he was only fifteen. He explains that her forceful presence gave him the discipline, focus, and confidence he needed to become a billionaire by his mid-twenties. Gatsby’s career is motivated by his desire to win Daisy back from Tom Buchannan; Christian’s has a somewhat less clearer purpose but seems connected to his panicked, desperate need to keep himself and the people he loves safe – a need that rises out of his traumatic childhood as the son of a “crack whore” (a phrase used in the novels with almost-comic frequency) who nearly starved to death when she died in their apartment and no one found him for several days.

Traditional fairy tales in which princes save princesses or other women are usually told from the perspective of the women who are saved. Fifty Shades adheres to this structure, more or less – although one could certainly argue that Ana saves Christian just as much as (or more so than) Christian saves Ana. The Great Gatsby, though, is told through, of all things, the perspective of the “prince’s” next-door-neighbor, a hapless but verbally gifted stockbroker from the Midwest. For this reason, the reader is kept at a distance from Daisy, who is as morally opaque when she runs down Myrtle Wilson in chapter 7 as she is in the novel’s first few pages, when she announces a propos of nothing that the best thing a woman can be is a “beautiful little fool.” Many of the complaints I’ve heard about the movie adaptation of Fifty Shades (interestingly enough, I don’t remember these sorts of complaints about the novels) have to do with the fact that Ana’s sexual initiation at the hands of Christian isn’t entirely consensual. The modern reader’s insistence on absolute openness, honesty, consent, and communication in sexual relationships balks at both the interior doubts Ana experiences and at the way Christian always takes such an assertive role in the progress of their sexual relationship. On the other hand, I’ve never heard anyone accuse Gatsby of sexual aggression, in spite of the fact that his initial coupling with Daisy (years before the novel begins) is described in the following terms: “He took what he could get, ravenously and unscrupulously – eventually he took Daisy one October night, took her because he had no real right to touch her hand.” It’s true that this statement would have seemed somewhat less untoward to one of Fitzgerald’s original readers than it does to a more modern sensibility, but nevertheless this is a harder statement, a more aggressive depiction of sexuality, than anything in Fifty Shades of Grey. The word ‘ravenously’ even comes from the same Latin root as the word ‘rape.’

It wasn’t until I started thinking of Jay and Grey as parallel characters that I realized how profoundly non-sexual Gatsby is. He has more in common with a plastic groom on top of a wedding cake than with an actual husband or lover. In Daisy’s presence he stammers and moves spasmodically and can barely carry on a conversation, so much so that Nick Carraway – no paragon of suavity himself – has to take him aside and say, “You’re acting like a little boy… Not only that, but you’re rude.” Christian, on the other hand, exudes sex. His home is built around his sexual proclivities. For a while (in the second book, I think) his former submissive sex partners pop up around every corner. He is as confident and efficient at bringing Ana to orgasm as Gatsby is pathetic when he shows up for his reunion with Daisy “pale as death, his hands plunged like weights in his coat pockets… standing in a puddle of water gazing tragically into [Nick’s] eyes.”

This essay represents the point-and-grunt method of literary criticism at its finest. I don’t have a theory, and I have nothing to tell you about the Great Truths of our Time. I am certainly not going to use the word zeitgeist. Nevertheless, the connection between these two fictional characters intrigues me. Is the fact that Grey is largely sexually appealing to readers and audiences while Gatsby is not simply the result of the fact that Grey’s creator is a heterosexual woman while Jay’s is a heterosexual man, or is there something more beneath the surface that impacts the way these men are perceived as lovers? Is wealth a more reliable indicator of sexual desirability than physical appearance? What about confidence? Which of the two characters is more dysfunctional from a contemporary pop-psychology perspective? (The conventional wisdom would say it’s Grey; I’m not sure I agree.) I wonder, too, what The Great Gatsby would be like if Fitzgerald had been writing in our era, when he would have more freedom to write explicitly about sex – and how Fifty Shades would be different if it had been written in an earlier era, when its author would have had to conceal so much of its life-force behind innuendo? I am reminded also of the recent movie adaptation of The Great Gatsby – of its near-cartoonish hyperbole and nonstop action. What would happen if Fifty Shades or one of its sequels were filmed in this manner, to emphasize the fact that, like Gatsby, it’s a fairy tale and not meant to be taken as a realistic depiction of a sexual relationship?

And that’s it. I have no answers. But, as always, it’s been fun formulating the questions.