"A Heartbreaking Work of Staggering Genius" (2000)

A Heartbreaking Work of Staggering Genius is a book that is, in an odd way, both in conflict with itself and with its own author.  It's a dazzling take on the memoir, but strictly speaking is listed as a novel -- though understood (and characterized by Eggers himself in his introduction) as an only somewhat fictionalized memoir. Along with allowing certain narrative conveniences, the fictionalizing of memoir allows a commentary on the expectations and absurdities of memoir itself.

Tim Parks noted this aspect of the book in a 2012 New York Review of Books piece:

Dave is given to wild exaggeration. He loves to tell tales, forgivable because hilarious, endearing because so obviously the product of a youthful desperation to achieve. The exaggeration seeps into the memoir itself; an interview where Dave explains to a TV producer why he should be on a reality show becomes a fifty-page tour-de-force. Much of what he tells the producer beggars belief, while the length and elaborate nature of the interview suggest that Eggers is exaggerating for us what exaggeration there may have been at this encounter, assuming it took place. 

Despite our amused skepticism, the technique works as memoir; this is the kind of person Dave is. We have not so much his life as his constant retelling of it. All is performance and persuasion with the present state of Dave’s mind the only topic on offer. Long conversations with Toph, for example, allow the younger boy to deconstruct, with sophistication beyond his years, the self-serving, pseudoethical positions Dave takes in his magazine. Rather than giving an accurate picture of Toph, it seems Dave is aware of his brother mostly insofar as he offers a foil to explore his own misgivings. After Toph lands one particularly eloquent blow, Dave protests: “You’re breaking out of character again.”

There's also, as maybe fits the book's own self-critique, Eggers' own subsequent distance from AHSWOG itself; after an extensive retrospective commentary in the first paperback edition, titled "Mistakes We Knew We Were Making" (excerpted here and here at the Guardian), he has rarely discussed the book since.

Part of that might be an understandable exhaustion with the subject; for all the astounding range of Eggers' subsequent work, AHWOSG is the first book that many people will mention.  (The fascinating Open Syllabus Project, which rounds up information from over a million syllabi to see what books colleges actually assign, shows AHWOSG way out in the lead among his works.)

So you may be tempted to assume that reader response and a varied subsequent career is at the root of this.  But there's a deeper ambivalence about the genre itself at work -- the very one expressed in the book itself, and in its paperback addendum. And it's one that Eggers laid out quite clearly in this NY Magazine profile before AHWOSG's release -- before that subsequent onslaught of publicity and reader reception:

He thinks all the postmodern reflexiveness will keep unwanted readers away. "I don't like the idea of it being a popular book; I think it would creep me out," he says. "Nobody likes the self-conscious stuff too much. I don't think the average Angela's Ashes reader will take to this. And the word motherfucker appears like 60 or 70 times." 

Tucked into one corner of the living room, there's a small shrine to the Eggers and McSweeney (his mother's maiden name) families -- just a few old photos and framed documents. And Eggers has no plans to write another memoir. "Never again," he says sharply. "It's one of those things where you completely get it out of your system and that's it." Now he's working on a novel written in the third person, with a woman as the main character. "I've gotten all that self-consciousness out of my system," he says. "Also, you get tired of using the word I. At least, I do."

One of his most extensive commentaries on memoir since then might be in his foreword to The Autobiographer's Handbook (2008), where he lauds the simple value of a familial record -- in his case, an account written by his great-great grandfather T.S. Hawkins, a founder of the California town of Hollister.  After his recent New Yorker piece on Hollister, Eggers has in fact just reissued Hawkins' Some Recollections of a Busy Life.