I’ve got to start with the blurbs. When, 25 years ago this month, I first picked up a copy of Dave Eggers’ A Heartbreaking Work of Staggering Genius, I immediately noticed that the back jacket sported the greatest collection of promotional quotes ever committed to print. It starts with a screed from the writer Jim Lewis—“This is a blurb. It conveys no information about the book whatsoever …”—that perfectly skewers the promotional journey on which we’re about to embark. The next three blurbs are from Davids middlebrow, upper-middlebrow, and highbrow: Sedaris, Remnick, and Foster Wallace, the latter’s lavish praise written in the second person and thus, thrillingly, plucked from a personal letter to the author. (“I thought the places where you cut loose and did arias of grief, like at the church, were the book’s best art.”) The litany ends with novelist Rick Moody bestowing upon the book an anti-endorsement that presages, in seven words, the memoir’s power, its inventiveness, and in many ways the inevitability of its success: “This book does not need a blurb.”
And A Heartbreaking Work of Staggering Genius was indeed a sensation. For much of 2000, the memoir was everywhere. It was a 14-week New York Times bestseller, a Times best book of the year, a Pulitzer Prize finalist. It swept through the media gossip ecosystem like a wildfire and made Eggers an inspirational figure, the target of envy, a literary crush object. It was so famous that when the producers of Friends wanted viewers to know that Tom Selleck’s character was an OK guy, even though he was Chandler’s rival, they put a copy of A Heartbreaking Work of Staggering Genius on his coffee table.
AHWOSG, as everyone, including its author, called it, launched Eggers’ career, one that’s seen him publish dozens of books, write screenplays, oversee a literary magazine and publishing company, and launch a nonprofit that’s helped hundreds of thousands of children become better writers. All those things happened because the book was a phenomenon—and a quarter century later, it seems clear that phenomenon is as much part of the book’s legacy as its literary risk-taking. This isn’t only because of the unlikelihood of an innovative, challenging book by a previously obscure author becoming a huge success. It’s because AHWOSG gave 29-year-old Dave Eggers everything that 23-year-old Dave Eggers ever dreamed of—and it was terrible.
The origin of AHWOSG was the kind of tragic tale made for memoir: When Eggers was still in college, both his parents died of cancer just a month apart from each other. The book’s first chapter agonizingly chronicles the illnesses of Heidi and John Eggers in Lake Forest, Illinois, then follows Dave and his 8-year-old brother Toph as they escape, fantastically, “through the window and fly up and over the quickly sketched trees and then to California.” In the Bay Area, where their older sister Beth is in law school, Eggers lives with Toph in a roommate/surrogate parent situation that Eggers characterizes as near feral but that, readers come to understand, is actually loving and supportive, if at times desperate.
But that’s just the story, and the story is not what most readers remember most clearly about AHWOSG. Even if you loved the book back then, you may not recall the rest of the book’s plot, which follows Dave’s twentysomething flounderings in a 1990s San Francisco about to be overwhelmed by tech money, primarily his work launching a scabrous satirical magazine called Might. But what I’m certain you do remember is the drawing of the stapler.
That drawing appears at the end of the book’s long, funny, bizarre front matter, everything that appears prior to Page 1. This encompasses xxxix pages, including: a copyright notice larded with gags; “Rules and Suggestions for the Enjoyment of This Book”; a collection of discarded epigraphs (including “Ooh, look at me, I’m Dave, I’m writing a book! With all my thoughts in it! La la la!” —Christopher Eggers); details as to what bits have been fictionalized; an acknowledgment that the author, too, has concerns about the title; an “incomplete guide to symbols and metaphors”; a breakdown of how he spent his $100,000 advance; and a long apologia for/defense of writing a memoir in the first place.
It’s that question—should he be writing about this at all?—that animates this front section, and really the entire book. Eggers addresses it from every angle, shamefacedly admitting that there are simply too many memoirs out there, defiantly noting that other writers are writing way worse books, confessing that the very idea of fictionalizing his story would have felt “like driving a car in a clown suit.” Toward the end of the “Acknowledgments” section, Eggers acknowledges “that no, he is not the only person to ever lose his parents, and that he is also not the only person ever to lose his parents and inherit a youngster. But he would like to point out that he is currently the only such person with a book contract.”
“Does there seem to be more meaning in these asides, footnotes, marginalia?” he once wrote in McSweeney’s. “Could it be that a group of writers, of a certain … age, feels more comfortable here, in the crevices, speaking their minds in these small, almost hidden ways, afraid to simply say things in plain language and bold type?” Or, as he put it in one of the “removed passages” of the book that he nonetheless found a way to insert back into the front matter: “See, I like the scaffolding. I like the scaffolding as much as I like the building. Especially if that scaffolding is beautiful, in its way.”
This scaffolding, combined with the book’s astonishing first few chapters, makes for exhilarating reading, a peak that the book struggles to match the rest of the way through. (Eggers being Eggers, he has anticipated this response, suggesting that many readers might want to stop after Page 109: “The book thereafter is kind of uneven.”) Rereading it now, I was surprised by how well the book manages to maintain the energy of those first hundred pages, considering that in many ways, the rest of the book is just Some Things That Happened to Dave. Some of the things are naturally dramatic, and some of the things are not, but such is Eggers’ skill at teasing meaning and emotion out of a scene—at taking an evocative moment and blowing it out through digression, flashback, and minutely observed detail—that a ride to the hospital with a painful kidney stone becomes an adventure for the ages. Much was made, when the book was published, of Eggers’ debt to David Foster Wallace, but in the structure of these chapters, I see the influence of Nicholson Baker, whose novel The Mezzanine unpacks a single escalator ride into a novel-length narrative whose real setting is not the lobby the narrator traverses but—as Eggers jokes (“jokes”) in AHWOSG—“the many twists and turns of his own thrilling and complex mind.”
I don’t know that I’ve ever read a book that is better at dramatizing—embodying—the feckless confidence of one’s early 20s, that feeling that if only you and your genius friends could be set loose upon society you could transform it, terraform the political and cultural and artistic structures of the earth and make a new world, a better one. Granted, from the standpoint of February 2025, when actual twentysomethings are doing the dark, horrible version of this in Washington, this prospect can be a bit alarming, but the immense humor and rage and charisma of the book nevertheless command your attention as a movie star commands the screen.
One of the book’s centerpieces is a retelling, in Q&A form, of Eggers’ in-person interview to be a cast member on the San Francisco season of MTV’s The Real World. In the book, Eggers has agonized over whether he should audition at all, whether to do so would make him a sellout or in fact would present him the opportunity to soar. Like many other dramatized conversations in AHWOSG, the Q&A—46 pages long, even longer than the book’s front matter—devours itself, transforming from quasi-realistic representation of an actual event to a meta self-interrogation, in which Eggers describes the comfort of his own upbringing, movingly reveals his late father’s alcoholism, and defends Gen X’s-obsession with itself.
“My feeling is that if you’re not self-obsessed you’re probably boring,” he says, claiming that the truly interesting people of his generation, the ones who will one day change the world, are the ones who are absolutely convinced that they have something important to offer, that they must be heard. It’s a comically messianic argument, though it’s also basically right.
In that same Q&A, Eggers makes another foray into defending his right to tell this story—defending the idea of transparent honesty, of revealing oneself, albeit in a format that’s deliberately obscurantist. In a fascinating rhetorical flourish, he does not lay claim to his own story but disavows it, surrenders it to the world. “These things aren’t even mine,” he writes. “My father is not mine—not in that way. His death and what he’s done are not mine.” He owns none of it, he says. “I do not claim exclusivity. Have it. Take it from me. Do with it what you will. Make it useful. This is like making electricity from dirt; it is almost too good to be believed, that we can make beauty from this stuff.”
“What about privacy?” his interlocutor asks.
“Cheap, overabundant, easily gotten, lost, regained, bought, sold.”
I still remember reading this section and thinking, yes. I understood that Eggers was not particularly fond of his younger self, that he was, at times, viciously satirizing that callow youth of a half-decade ago. “The goal was to make it painfully honest,” he’d said. “To make it hurt me. Again and again I tried to make it so that I looked as bad as I could, as I was.” Later he would describe the entire project of the book as “public embarrassment as punishment for living on.” And yet I read this and understood the bravery involved in such a claim, and thought, yes. No other book has ever made me want to write the way this book did.
But the book itself was just the beginning of the life of A Heartbreaking Work of Staggering Genius. The story, thereafter, is somewhat uneven.
It is difficult to overstate just what a phenomenon AHWOSG was upon its publication in February 2000. The book benefited from a masterfully conducted traditional campaign, one that leveraged the news media in all the ways a publicist might dream of. The New Yorker featured an enormous excerpt, more than 6,000 words, published in the same issue as a photo of Eggers and his cohort at the literary magazine McSweeney’s with a short ode to how cool they were. (The rubric: “The Next Generation,” a catchall under which the magazine also introduced its readers to Zadie Smith and Paris Hilton.) Michiko Kakutani wrote one of her name-making raves in the New York Times. (“A virtuosic piece of writing, a big, daring, manic-depressive stew of a book that noisily announces the debut of a talented—yes, staggeringly talented new writer.”) There was a profile in the same paper. A profile in New York magazine. A profile in the Washington Post. The blitz was so intensive that the New York Observer’s media reporter, Gabriel Snyder, devoted an entire column to chronicling it. Every print and online publication weighed in (Slate very much included). The only one that didn’t cover the book was Esquire, which was rumored to have banned Eggers’ name from the publication after Eggers skewered his former workplace in McSweeney’s.
I read it all. I devoured it. I was obsessed with the book, with McSweeney’s, with the elegant dance that Eggers seemed to be doing, pirouetting between sincerity and cynicism, ingenuousness and jadedness. I felt just as ambitious and just as at sea, and couldn’t believe someone had put into the world not just a book but an entire ethos, it seemed, that perfectly spoke to how I wanted to matter, the inchoate but powerful desire I felt to make something of myself. The book’s front matter featured one of Eggers’ bits of gnomic wisdom, the aphorisms he liked to sprinkle across his work:
Vintage
I was tired. I was true of heart!
And meanwhile, a grassroots, online fan community was growing. On Salon’s message board “Table Talk,” in an endless comment thread on the Atlantic’s website, and on the Letters page of McSweeney’s itself, devotees of the book and of Eggers’ whole vibe formed a movement of sorts. They discussed Eggers’ work, and their own, and met in person at Eggers’ book events, which were barely readings at all—more literary carnivals, full of jokes, stunts, and the occasional appearance by Eggers’ high school classmate Vince Vaughn. (Read this unhinged but utterly compelling reminiscence to see what the fan scene was like at its best and its worst.)
As the year went on, as AHWOSG occupied the Times bestseller list for months on end, the attention rose to a fever pitch. Rosie O’Donnell, a fan, tried to get Eggers to appear on her daytime show and settled for auctioning off his half-eaten breakfast for charity. Online parodists posited Eggers as a future dating-show contestant, or mashed up Eggers and fellow bestseller J.K. Rowling. (They even parodied the blurbs.) Someone launched a fake McSweeney’s site and, reportedly, replied to confused emailers as if they were actually Eggers. A future bestselling novelist blogged about trying to meet “famous dreamboat” Dave Eggers. A future National Book Award finalist said she’d like to punch Eggers in the face. A high school student posted Friends of Eggers, comprehensive, increasingly snotty recaps of Eggersverse news, chronicling the author’s friends, enemies, and “wannabes.”
And Eggers, who had wryly chronicled his youthful, unquenchable thirst for fame, saw that thirst quenched in an instant. How did it feel? “It sucks shit,” he was saying by March, less than a month after the book’s release. Besieged by press, Eggers soon stopped doing phone or in-person interviews, insisting upon emailed Q&As, and then only if he was assured they would run unedited. In one of those, with a student at the Harvard Advocate, Eggers belittled the interviewer—“Had this been asked in another, less glib, way, I would have answered,” he responded to an innocuous query about movie rights—and also issued a much-reprinted screed against the concept of “selling out,” against the critical impulse itself:
Do not be critics, you people, I beg you. I was a critic and I wish I could take it all back because it came from a smelly and ignorant place in me, and spoke with a voice that was all rage and envy. Do not dismiss a book until you have written one, and do not dismiss a movie until you have made one, and do not dismiss a person until you have met them. It is a fuckload of work to be open-minded and generous and understanding and forgiving and accepting, but Christ, that is what matters.
Eggers, who once tweaked celebrities and literary titans on the pages of Might, told LA Weekly he found it interesting to see “the same tricks that I used to pull as a young asshole being pulled on me.” But while he hated what was happening to him, he found solace—indeed, meaning—in the fact that the money he was making was being put to use: charity contributions, artist grants, and the growing McSweeney’s publishing project. “We’re publishing four books by the summer. That’s the whole point. If I need to be sacrificed in order to do that, that’s fine.”
In April, the high school student who blogged Friends of Eggers published emails he’d received from Beth, Dave’s older sister, in which she complained about how she’d been portrayed in the book. After the emails were reprinted in Harper’s that summer, she professed her sadness and embarrassment that she’d ever written them. “We are not sure why they, or anyone, would want to act in a way that would hurt our family, which, we feel, has already had our share of difficulties,” Dave Eggers wrote on McSweeney’s, in a message that was careful to criticize only Harper’s and not the teenage fan. “We are begging for less malice.”
The hysteria climaxed in early 2001, with the publication of the paperback edition. Inventively packaged—turn the book over, and you’d find a new addendum, titled Mistakes We Knew We Were Making, 48 more pages of corrections, jokes, and cris de coeur—the paperback was an instant No. 1 bestseller. When the New York Times ran a feature about the paperback, Eggers published a piqued 10,000-word “Clarification” that reprinted, in full, his correspondence with the Times. “My guess is you don’t think you come off too well, and you wish you could take each person reading this aside and try to explain,” he wrote to the reporter. “Welcome to the club.”
Eggers never, to my knowledge, complained about the readers who had found the book so thrilling—who surely dogged him online and in person as mercilessly as the press did. In Mistakes We Knew We Were Making, he describes how affecting it could be to connect with those readers. Nevertheless, the fulfillment of Eggers’ literary dreams had turned out to be a kind of torture, one he’d seemed to foresee. “You think you want people to know that stuff, and then after you’ve written it, you go, ‘Oh, fuck—I don’t really want anyone to know any of that stuff,’ ” he told New York magazine in the weeks before the book’s release. “In a way, it’s sort of like a letter you write that you should have waited before you sent it.”
I don’t think Eggers feels any differently now. (Certainly his family has had its share of further difficulties in the years since: In November 2001, Beth died by suicide, and last year, Christopher Eggers told the Hollywood Reporter that he and Dave are estranged. The reporter who broke that story is, unnervingly, the former blogger who, 25 years ago, wrote Friends of Eggers.) My guess is that Eggers has not minded the lack of 25th anniversary fanfare for AHWOSG, a book of which he’s said that, if he had to do it over, “I might have fictionalized it. Or made it semiautobiographical fiction. Or set it in the Old West.”
But though AHWOSG no longer has the profile it once did—according to Bookscan, which covers about 85 percent of U.S. book sales, it sells about 2,000 copies a year—I think it’s still important to remember, and to recognize. Both the book and the whirlwind that surrounded the book transformed how writers thought about what personal writing can do, and what a writing career should be. “In the way Bob Dylan going electric allowed every other folk singer to go electric,” the writer Lawrence Weschler said, “Eggers gave permission with voice to a whole new generation.”
Memoirs have gone in and out of fashion since 2000. They were declared dead following the James Frey debacle, yet memoirs by regular people, demi-celebrities, and even future vice presidents still succeed. While none of those books have matched Eggers’ for inventiveness (few can), the past quarter century has been a rich period for self-aware, voicey confessional writing—thanks in large part to the 2000s blog boom, some of the most prominent writers of which once filled those Eggers-adjacent comment threads with their opinions, as well as its reverberations everywhere from social media to Substack.
When I wrote my own 2019 memoir, I found that I, too, wrestled with the question Eggers wrestled with in AHWOSG—whether my story was worth telling—and that, as he did, I chose to handle that dilemma by confronting it head-on. I’m not the only one. “He put it all on the page. I realize now that I do that too,” said Nicole Graev Lipson, whose memoir Mothers and Other Fictional Characters publishes in March. “If he’s concerned about what readers are going to think, he’s just going to lay it out.”
In 2000 Lipson was the assistant to the Simon and Schuster editor who acquired AHWOSG, and she still remembers the thrill of reading the first pages of the memoir as it came in. (She’s immortalized on the final page of those acknowledgments, “right above the drawing of the stapler,” she said. “I dined out off that a long time.”) When she left the job to become a writer, she recalled, Eggers gave her a very supportive phone call. “Those things mean a lot to an aspiring writer, when a writer you admire makes you feel like you’re doing the same thing as him.”
Her experience, of feeling encouraged by Dave Eggers, is not uncommon. For all Eggers’ prickliness, it seems indisputable that his post-AHWOSG career has been good for art, good for literature, and good for the world. Even leaving aside his own subsequent books—which have been finalists for the National Book and National Book Critics Circle awards, and just last year won Eggers the Newbery Medal—McSweeney’s, now a nonprofit, has published scores of titles by ambitious young writers alongside big names like Miranda July, Michael Chabon, and Nick Hornby. Last year, one of its books, Sam Sax’s inventive debut novel Yr Dead, was longlisted for the National Book Award. McSweeney’s literary journal has won multiple National Magazine Awards. The nonprofit Eggers helped found, 826 National, has taught writing workshops to more than 600,000 young people. None of this would have happened if Dave Eggers hadn’t written AHWOSG, hadn’t spent the money he made on it—“silly money,” he wrote in Mistakes We Knew We Were Making, “money that was never mine and could never be mine”—on things that mattered to him.
And this, too, has been a lesson of AHWOSG: that writing about yourself might be painful, unbearable even. That people might misread your work, act with malice, take the wrong things from it—or even take the right things from it in such unbelievable numbers that you sort of wish you’d never written it in the first place. And yet it might all still, somehow, be worth it. That’s the conclusion Eggers reaches in Mistakes We Knew We Were Making, his final word on his first book. He wrote much of the addendum in a rush in September 2000, including a passage that I never saw back then but that I find immensely moving now.
I was ashamed, because I had written what I saw as a much too revealing and maudlin thing, overflowing with blood and sentiment and a simple bare longing for people who are gone. The book was seen by its author as a stupid risk, and an ugly thing, and a betrayal, and overall, as a mistake he would regret for the rest of his life but a mistake which nevertheless he could not refrain from making and worse, as a mistake he would encourage everyone to make, because everyone should make big, huge mistakes.
That Dave Eggers published such a heartfelt defense of radical honesty in personal writing, in type so tiny I can barely read it, in material he deleted from later editions of the paperback, feels just about right. I hope Eggers never has to answer another question about A Heartbreaking Work of Staggering Genius in his life. But I’m grateful for the big, huge mistake he made by writing it, and I hope that people keep on reading it, long after we’re all gone.
