A Q & A with Christopher Castellani

Last Seen starts out with an intriguing premise: Four young men—Caleb, Matthew, Leo, and Steven—watching in on their loved ones from beyond the grave. Talk a bit about the plot of the novel.

Because the reader knows the fate of the four main characters from the flap copy, the primary drivers of the plot of Last Seen are, “how did these boys die, and why?” A secondary but crucial driver is, “are their deaths connected in some way?”

The present action begins in March 2020 when a man named James Hahn, who’s spent the last thirteen years trying to answer these questions, learns of the mysterious disappearance of University of Michigan student Matthew Cardullo. Matthew’s case reminds James of Caleb, the college boy with whom he had a secret love affair back in 2007. Caleb’s still-unsolved disappearance is what first ignited James’s obsession with the Smiley Face Murder Theory, an implausible but enthralling explanation for why young men like Matthew and Caleb keep turning up dead in bodies of water from New England to the upper Midwest.

As James tries to piece together what happened to Caleb, Matthew, Steven Donovan, Leo Ridgway, and the dozens of other supposed Smiley Face victims, the “victims” themselves — suspended in a limbo-like afterlife — are on a similar journey of understanding the why and how of their deaths and what, if anything, their otherwise ordinary lives meant. The boys speak directly not only to the reader, but to each other, forming a kind of community of lost souls. With varying degrees of success, they try to make contact with the one living person they can see from the beyond, who also happens to be the person they love most in the world. For Caleb, that’s James Hahn. For Matthew, it’s his mother, Lori. For Steven Donovan, last seen drunkenly wandering the streets of Boston, it’s his married lover, Monica. For Leo Ridgeway of St. Paul, Minnesota, son of a once-famous father and junkie mother, it’s his younger sibling, also named Leo, who was named Katie at birth.

Over the course of the novel, in scenes that stretch into 2035 and beyond, James, Lori, Monica, and Leo III offer crucial details and insights that not only complete the stories of Caleb, Matthew, Steven and Leo II, but reveal how their sudden deaths irrevocably altered the trajectories of their own lives.

This book is a bit of a departure from your previous work. Your past novels have mostly been historical — Leading Men was about Tennessee Williams; the “Maddalena Trilogy” about three generations of an Italian-American family — but Last Seen incorporates elements of suspense, true crime, and magical realism. Was that your goal when you started writing?

My only goal when I first started writing was to fully inhabit the bodies, hearts, and minds of the four main characters, as well as the loved ones they left behind. Because I never outline or try to impose themes or devices on any of my novels, the suspense and magical realism came as complete surprises to me, which I hope makes them feel so organic to the story that the reader can’t imagine Last Seen being told any other way. In fact, in early drafts, I tried to tell this story as straight realism, but I couldn’t find my footing; it wasn’t until I heard the voices of the boys calling to me from their murky afterlives that the project finally “clicked.”

Given that the fates of the four boys were inspired by the real-life cases associated with the Smiley Face Murder Theory, I knew I was venturing dangerously close to the genre of True Crime, but my goal was never to satisfy that particular genre’s demands, or even to include elements of a traditional mystery. As in any literary novel, the goal was to narrativize the experiences of characters who fascinated me in a way that felt as true and human as possible, capturing their voices with language as precise as I could make it.

All that said, Agatha Christie was my first true reading obsession. In middle school, thanks to the local library, I read every single one of her mystery novels and reviewed them Goodreads-style in a black-and-white composition notebook I proudly shared with the librarian on each weekly visit. So, it’s possible that the seeds of Last Seen were planted back in the mid-1980s and have just now borne fruit.

Last Seen also has a unique structure. There are sections narrated by Caleb, Matthew, Leo, and Steven, and by the people they’ve left behind, all interweaving. How did you approach piecing the characters and their arcs together?

This book always felt bigger to me than a single person’s story. The vision in my head was never of one life but of a mosaic of lives — a collection of characters that are adjacent and interrelated but not necessarily overlapping. In a mosaic, each piece is a different shape and size and color; they rub up against each other, but only on one or two sides; many don’t touch each other at all; but when you put all the pieces together, they form a coherent (if shattered) image that would appear incomplete without every single piece in its rightful place. This is one reason why I told Last Seen in twenty-six differently-shaped sections arranged out of chronological order, no two of which are the same length or tone. They are grouped into themed sections, however, and titled with variations on the Seen/Scene pun: Crime Seen, First Seen, Love Seen, etc. I think of these themed sections as the “grout” that holds the seemingly disparate pieces of the mosaic together, and which helps the pieces form that coherent image by the end.

Once I conceived of this structure, it became my intention for the reader not to fully “see” the entirety of the image until the very last piece is put in place. Along the way, I wanted the reader to get the same kind of pleasure and satisfaction they might get from doing a jigsaw puzzle, the joy of which comes not only from fitting the last piece in its center but from assembling first its edges, then its patch of blue sky, then that flock of birds in the top-right corner…Without those satisfying little victories and visions and mini-resolutions to little mysteries along the way, reading (and puzzling) are much less fun.

One throughline in the book is the Smiley Face Killer theory. Caleb’s boyfriend, James, becomes convinced that Caleb was a victim. What is this theory, and why did you want to explore it in fiction?

The Smiley Face Murder Theory posits that, over the past thirty-ish years, a vast and shadowy network of serial killers has been stalking college-aged men, kidnapping them, and then depositing their bodies in various icy rivers and lakes across the country. The Killers’ name comes from their signature: a single graffito of a smiley face they spray-paint on a nearby rock or bridge after dumping the body.

Two retired New York City police detectives — Roger Gannon and Anthony Duarte — were the first to promulgate the Smiley Face Murder Theory, which has been routinely investigated by law enforcement agencies and the FBI, among other groups, since the late 1990s. Despite its implausibility, and the fact that no hard evidence has been found to support it, the theory has proven to be remarkably resilient, perhaps in part because college-aged boys continue to go missing and/or turn up dead in various bodies of water with alarming frequency. Most such cases get solved soon after: the boys are determined to be runaways, or to have died by accident or suicide or at the hands of a mugger or someone they knew. However, dozens of the unsolved or inconclusively-solved cases share striking similarities, and not just the presence of the smiley-face graffito. For example, the boys in question have many demographic traits in common: they’re college-aged, living in New England or the Upper Midwest, traditionally handsome, white, straight, athletic, good in school, and were last seen by their friends leaving a bar or party at which they’d been happily drinking; their corpses show little sign of trauma or sexual violation; and, most eerily, they’re found floating supine with their arms crossed in an X over their chests.

For the record, I’m not interested in whether the Smiley Face Murder Theory is real; I’ve always been quite confident, from just the most casual research, that it’s not. But I am interested in the theory’s remarkable persistence in our psyche, as it seems to be an uniquely American phenomenon. Why do countless articles, documentaries, Reddit threads, and blogs continue to be written by people of all ages and genders and backgrounds obsessed with this far-fetched and widely debunked theory — myself included? What need does it fulfill for us to think of our strong, vital, American boys as somehow endangered? Why do we imagine this highly-organized “network” — presumably of men who are older? Less strong, less vital? Less white or less “American,” perhaps? — might be motivated to target and punish them? I think Smiley Face appeals to some of the darker and more fear-based aspects of our natures: our desire for retribution, our fetishization of a particular brand of masculinity, and our fundamental distrust of each other, to name just a few.

All of these are present, in various forms, in Last Seen. So is, more personally, the particular grief of losing a loved one who was so young and promising, and how the aftershocks of such a loss can still be felt decades later. Ultimately, though, I wrote about Smiley Face in fiction because I wanted to hear about all these things from the boys’ point of view; I was curious what they had to say about the choices they made in their lives, about how they construct and “see” themselves. That’s what literary fiction does best, of course: it gives people who’ve been stripped of their full humanity — by victimhood, by hero-worship, by the various demands of culture they were born into but didn’t necessarily create, by oppressive forms of socialization — the dignity of an inner life.

Caleb, Matthew, Leo, and Steven — in life and in death — all struggle with their own notions of masculinity. The state of masculinity in America is a hot-button issue right now. What made you want to explore this theme?

I finished Last Seen in October 2024, just before the presidential election, and right around the time the heat on this issue got turned up to high. As I was working on it, I wasn’t as consciously aware of masculinity as a political issue as I would be if I were working on the novel today — and, in my opinion, that’s a really good thing. I don’t think people read literary novels to be preached to or to have their worldviews validated. I think we pick up a literary novel because we crave the sort of deep dive into the murkiness and moral complexity of the human condition that such character-based and language-forward stories can provide. So that’s what I was trying to the best of my abilities to accomplish: an honest portrayal of four of the types of young men at the center of the Smiley Face cases, who suddenly just happen to be the ones at the center of our current political and cultural discourse.

From what I’ve observed of such men, “masculinity” as a facet of their identity informs virtually every decision they make and every emotion they express (though not necessarily every emotion they feel). Almost to the point of a punch line, the inability of men to communicate what’s in their hearts and on their minds has always been synonymous with masculinity itself. Matthew, Caleb, Steven and Leo — the four main characters in Last Seen — are coming of age in the early twentieth-century, a time when expectations for and definitions of what it means to be male and “masculine” in America are rapidly changing; they are the young men most deeply affected by the “loneliness epidemic”; meanwhile, they are struggling to learn an ever-evolving language for how to express their desires and ambitions and fears and senses of self both with the people they love and with each other. I can’t think of a more compelling group of people to try and understand, and empathize with, at this moment in our country, even/especially if I don’t agree with or relate to them on everything. For that reason, I’m grateful that I wrote this novel before the discourse got overdetermined by a million think pieces on the nature of the “manosphere.”

A line from Elena Ferrante — “Each of us narrates our life as it suits us” — became my guiding principle for the sections of the novel where my four young male protagonists tell their life stories unfiltered and uninterrupted. This is why, in those soliloquies, they are alternately withholding and confessing, bullshitting and truth-telling, boasting and self-effacing. I want readers to believe them, but not necessarily trust them. As they interrogate their own and each other’s moral character, so should we.

Your last book, Leading Men, is currently being adapted into a feature film produced by Searchlight pictures and Nomadland’s Peter Spears. What can you tell us about it?

Only that it’s been a joy to work with Searchlight and Peter Spears — a true mensch who is committed to the artistic integrity of all his film projects — and with everyone who’s been involved in the long and roller-coastery process. Peter optioned the novel a few months after it was published in spring 2019, and since then has renewed it again and again through a global pandemic, a writers’ strike, and the coming-and-going of a screenwriter and a marquee director. While I can’t divulge any concrete details, I can say that the project is still very much alive and that we may have some exciting news on it soon.

What do you hope readers take away from Last Seen?

Mostly I hope readers will fall in a complicated kind of love with all of these characters, despite — or maybe even because of — their flaws and deceptions and self-obsessions. This is true not only for the four boys at the center of the narrative, but for the people they left behind, none of whom is meant to be a hero or a villain.

I also hope readers will have strong opinions about the characters involved in the various types of romantic and familial relationships I explore, in particular so-called “age-gap” relationships; queer relationships; open relationships; the relationship between a mother and her autistic son; and the powerful bond between a brother and his younger sibling who transitions over the course of the novel.

I hope readers will catch the “Easter egg” in the character of Derrick, who is an homage to a character in an iconic work of gay literature.

This is my sentimental side coming out, but I also hope that, by hearing the voices of four young men who’ve died but are still connected to the ones they love most, readers will imagine that their own loved ones who’ve passed are still beside them somehow, and that this will make readers feel, even for just a moment, less alone. ▣