IN JIMMY CORRIGAN: The Smartest Kid on Earth (2000) and Building Stories (2012), Chris Ware has already produced two of the most artistically ambitious and paradigm-exploding works of contemporary comic art available anywhere. So it’s fair to say that expectations for the publication of his long-running serial Rusty Brown are extremely high. The complex interplay between originality and repetition tends to become an overarching concern in the middle period of any successful artist, no matter the medium they work in. How can someone produce art that is in continuity with, but not a bare retread of, the work that made them famous? And then how can do they do it over and over again, for decades at a stretch? Nearly anyone who becomes renowned as an auteur eventually faces the moment when critical reception of their work collapses into frustration with their stylistic tics, their thematic obsessions, their blind spots and omissions.

In Ware’s case, the critics have been especially preoccupied with the melancholic cynicism about the possibility for human fulfillment that is central to his work. This cynicism, which Isaac Butler recently called “miserablism,” has been so intense and unrelenting that it once led Douglas Wolk to query, “Why Does Chris Ware Hate Fun?”

With this in mind, how can Rusty Brown — a work Ware has been composing for over 16 years, and which he publishes here still only half-completed — possibly escape the shadow of what came before? When we open the cellophane encasing the book we discover elements of Ware’s creative process we recognize immediately: his famous Peanuts-like caricatures and bright primary colors; his penchant for diagrams, graphs, maps, and snowy tableaus; and his trademark, bitterly self-deprecating micro-comics. Haven’t we been here before?

To some extent we have, though the book eventually moves us out of that orbit. The opening sections seem like a remix of concerns from earlier Ware comics, especially Jimmy Corrigan. We once again settle on disaffected, unhappy boys, preoccupied with superheroes and their toys, clinging pathetically to a childhood that is slipping away, even as it wasn’t all that happy or nurturing to begin with. Teaching Ware for the last 15 years or so, I have seen classroom after classroom starkly divide on such betrayals, with half the students utterly revolted by Ware’s acerbic, intensely unlikable protagonists and the other half seeing in them an unexpected and perhaps not altogether welcome reflection of their own lifelong deficiencies and pathologies.

Jimmy Corrigan’s inside front cover was adorned with a quiz to see if you were personally damaged enough to be a successful reader of the book (with the first question jokingly telling women they might as well just put the book away right now). The first volume of Rusty Brown dispenses with the quiz and instead stamps the copyright page with a “THIS BOOK IS THE PROPERTY OF” seal reminiscent of public-school textbooks. The owner is listed as Rusty Brown: if you own the book, you’re already him.

In Rusty Brown’s long introductory section, we follow Rusty and his soon-to-be best frenemy Chalky White on the day of their first meeting, over the long course of a single day at the private school they attend. Rusty’s father is a teacher at the school, as is a fictionalized and aggressively creepy version of Ware himself. Fans of Ware’s periodic Acme Novelty Library publications may recognize Rusty and Chalky from published excerpts of the series, but most of their contentious relationship will happen after this day’s events — and indeed, after this first section, Rusty Brown mostly pushes Rusty into the background, focusing on the pulp-science-fiction fantasies of his sad-sack (and also pretty creepy) father in the second major section, and moving on to even more ancillary characters in the third and fourth.

I suspect many of the critical conversations around Rusty Brown’s first volume will revolve around the book’s transcendent third section, an 80-page cradle-to-grave study of the life of one of Rusty’s older teenage bullies, Jordan Wellington “Jason” Lint III, that invites comparison to the high-modernist stream-of-consciousness narration of Ulysses or Finnegans Wake. We begin with an almost pointillist, black-and-white-and-red abstraction of a human face, which we come to understand is how an infant Jordan sees himself. Soon his mother and father come into focus as well, body part by body part. The section next depicts the growth of Jordan’s language comprehension, showing Jordan’s name morphing from total gibberish to “jRdn” to its final form, and then providing a tableau of an entire world in which each object is labeled by a simple color or noun. Subsequently Jordan’s early acquisition of language contorts into a nightmarish study of a child being screamed at over and over again (“No, Jordan! No! Bad!”), as well as confused recognition of the domestic violence in his household. That same rage soon manifests in Jordan himself, alongside a possessive attitude toward the toys with which he plays (“Mine! Mine!”). And so we watch Jordan — who renames himself Jason after his mother’s early death and his father’s remarriage — transforming from an unhappy kid into a horny young teenager, then a cruel and homophobic bully, statutory rapist, burnout, and twentysomething addict who chases a hopeless music career while sponging off his father’s wealth.

But, remarkably, Jason cleans up his act. He starts working for his father’s firm, meets a girl, falls in love, and enters recovery. He gets married and has a son, becomes a devoted dad, and rises in the ranks at the company. He reads The 7 Habits of Highly Effective People and clips inspirational quotes from Pierre Teilhard de Chardin (“We are not human beings on a spiritual journey. We are spiritual beings on a human journey.”). When Jason briefly encounters an adult Rusty Brown at a supermarket in their hometown, he seeks connection with him, but a distressed Brown recoils from the contact — and Jason reflects on the encounter with a mix of pity and guilt that seems appropriately mature, if still a little self-involved. Jason even finds religion, and begs forgiveness for his sins. Around the halfway mark of the book, Jordan Lint tells us, “Finally, I have found grace. Finally, I have found love. Finally — I have found myself.”

And then, just as remarkably — in what seems like brutal confirmation of the proposition that Chris Ware hates not just fun but hope itself — it all completely goes to hell. Jordan cheats on the wife he thinks saved his soul with a young woman from his church, and soon enough he cheats on her, too. He gets drunk at his father’s 65th birthday party, and the next time we see him he is divorced, sporting a new, thinner look complete with dyed-black hair and a goatee (as well as a growing bald spot). We see signs that Jordan is making money through criminal commingling and embezzlement of his clients’ funds. When we encounter Jordan near the end of his life, he is bankrupt and miserable, trapped in a prison of bad memories, excuse-making, self-pity, and regrets, haunted by the ghosts of the people he has hurt but still unable to take any responsibility. “Why? Why did my father hate me so much?” he pathetically asks his second wife on the day that sees the end of his career. By the end, even she is surprised by how petty and mean he’s become (“You really are a fucking bastard, aren’t you?”).

Then the story takes an even darker turn. As Jordan enters old age, we learn that when he was younger he committed a horrible act — one we never saw, because an ashamed and deluded Jordan has never allowed himself to think about it. We encounter it now, from the victim’s perspective, in images depicting the world as a jagged, nightmarish sea of red, overawed by Jordan’s monstrous face. As Jordan grows older still, the form of the story once again shifts: he falls into a sea of senile dementia that returns him to the disordered, abstracted thinking that characterized his infancy, before finally drifting away into total loss of self during a half-remembered reverie of another horrible act committed decades earlier. Ware, it turns out, has made us experience Jordan’s own carefully constructed facade of redemption, only to finally pull back the curtain on the horrors it concealed all along.

Ware’s appreciation of the radical horror of being — the sheer dread that comes with existing at all, the guilt and sorrow that comes with living a life you can’t take back — reaches an absolute pinnacle in these pages, which easily could have been published on their own as a short novella. The sheer artistic achievement of this spellbinding sequence is matched only by its totalizing cosmic pessimism: we are born to suffer; we become monsters before we are even aware enough to choose or to know better; we are incapable of growing or changing, much less ever being happy. The true enormity of our failures and our crimes against each other and against ourselves is always at the edge of our consciousness, simply waiting for the moment of terrible and final revelation. If, for a certain type of reader, this all feels absolutely and unalterably true, whether we’d like it to be or not, for another type of reader it is, I imagine, a biting portrait of human misery that could seem genuinely unbearable to endure.

Me? It made me so incredibly sad. I loved it.

Despite Ware’s unparalleled mastery of the art of losing, there are hints in Rusty Brown, as in the artist’s other major works, that he might prefer to be the second sort of reader, despite his own habits of thinking and his global reputation as a deeply depressed creative. In the final section of Rusty Brown Volume 1, we turn to the story of Joanne Cole, Rusty’s teacher and later the principal of the school he and Jordan attended. A black woman working in a district whose teachers and students are mostly white, Cole is determined and confident, but worn down by the racism of her surroundings and haunted by the memory of the child she gave up in a closed adoption as a teenager. The final cliffhanger of the book sees this child, Janice Woods, returning to Cole’s life and comforting her as she breaks down into sobs of joy and regret — a miracle of genuine parent-child reconciliation of the sort that has seemingly been foreclosed everywhere else in Ware’s work.

As we head into the gap between volumes Ware labels “Intermission,” Janice explains that she wasn’t going to contact Joanne at all, but she was pushed to do so by a co-worker. We find, in a teeny-tiny footnote, that this co-worker was Jimmy Corrigan’s sister, Amy, whom we last saw lonely, depressed, and working on Thanksgiving Day. Here, perhaps, Ware calls his critics’ bluff: Rusty Brown is not just a spiritual but also a literal sequel to Jimmy Corrigan. And perhaps Amy is still alone, perhaps she’s still depressed. But we learn here that she has been a source of comfort and support to her friend, suggesting the character has not allowed herself to become bitter or broken the way the end of Jimmy Corrigan suggested she might have. Can we imagine Amy Corrigan happy? Satisfied? Personally fulfilled? Having it all?

Of course, if we’d cut Jordan’s story off in the middle, it would have looked like a story of redemption, too. And maybe Joanne’s miracle will turn sour in the same way in the next volume. But maybe it won’t. Surely, at least every once in a while, the brilliant omniscience of Ware’s artistic style can produce a happy ending, too. The weird, wondrous reversal at the end of Joanne’s story, complete with a link back to Ware’s most famous work and the unexpected revision of its mirthless ending, offers up a fragile hope that Rusty Brown Volume 2, whenever it arrives, might yet have something new to show us beyond Ware’s trademark excruciating beauty and meticulously crafted, gloriously intricate despair.

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Gerry Canavan is an associate professor of contemporary literature at Marquette University and the author of Octavia E. Butler.