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Published on November 5th, 2014 | by Jay Rachel Edidin

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Looking for Lucky Wander Boy

The pareidolia of D.B. Weiss’s 2003 novel Lucky Wander Boy is pervasive, compelling, contagious. My notes for this article—assembled as I re-read the book for the first time in nearly a decade—look like a text-only analogue to a pinboard out of A Beautiful Mind: works with tangential thematic or structural connections to Lucky Wander Boy; quotations from the book and elsewhere; citations marked “real” or “Weiss” depending on the sources I could find. I found myself looking up the date of the final post on the original Gaming Intelligence Agency—March 31, 2002—to compare it to the original release date of Lucky Wander Boy—February 2003.

The name at the center of this metaphorical red-string map—to what extent it has a center—is Marc Laidlaw, best known as the writer of Half-Life series, and the first person I met who had found Lucky Wander Boy through means unconnected to me. I met Marc when I was an editor at Dark Horse; he had a story in an anthology for which I served as in-house editor. Later we talked on and off about putting together a collection of his short fiction; and it was through him that I ended up in touch with and editing books from Valve, but that’s irrelevant.

What is relevant—or seems like it should be—is that Marc was also an old-school Gaming Intelligence Agency fan. He was the one who told me that the GIA had been revived, last PAX, over fancy beers and truffle-infused popcorn at a pub whose name I’ve forgotten but which was my go-to for work meetings in 2013. It was Marc who first put me in touch with Andrew Vestal, who at that point had existed in my mind as a sort of abstract entity for over a dozen years; and who had also read Lucky Wander Boy and originally suggested this article.

The catch, of course, is that this is all sleight of hand. None of it actually matters—not Marc, not the pedigree of my relationship to this site. It’s possible that the GIA, intricate and high-mindedly absurd, primed my palate for Lucky Wander Boy, but if so, it was one of dozens of such aperitifs. It matters roughly as much as the fact that my name has the same number of syllables, the same rough cadence, as both Adam Pennyman, and, by extension, Lucky Wander Boy.

That’s the sort of thing this book does to my head.


The first thing I read at the GIA—back in 1999, when I was a senior in high school, four years before Lucky Wander Boy would hit the stands—was a piece of fan fiction. I read it on my boyfriend’s computer; the same boyfriend who, by means of impassioned “video games are art” speeches and the impressive-for-its-time opening cinematic to Final Fantasy VIII, had also talked me into getting my first game console the previous year. The story was called “Dirt Angels,” and it was by someone who went by Matthew Shuele—presumably a pseudonym, since “Dirt Angels” is the only link Google yields in connection to Shuele’s name.

You can still read “Dirt Angels” on the GIA archive, if you’re so inclined; I did, tonight. It’s not bad, even at 32 instead of 16, even with a writing and editing career in the difference. But that’s not important, either.

The important thing about “Dirt Angels”—at least as it applies to the GIA as I found it in 1999; and, by extension, as it applies to Lucky Wander Boy—is what it’s about; or, rather, what it’s not. It’s Final Fantasy VII fanfiction, but it’s not about Cloud or Sephiroth or any of the main characters, or any characters who even appear in the game. “Dirt Angels” spins off from a piece of throwaway set dressing from the game’s first act: a name scrawled haphazardly across a crumbling wall; incidental minutiae infused with new and poignant meaning.


luckywanderboy-cover“Back then, I harbored an inchoate version of a suspicion I still harbor today: that the intrinsic value of a thing is directly proportional to its initial impenetrability, and that things worth knowing often cloak themselves in hall-of-mirrors absurdity to scare off dabblers and those seeking choice small-talk nuggets.”

—D. B. Weiss, Lucky Wander Boy

To describe Lucky Wander Boy as “dense” is a radical understatement. It’s crenellated, fractal, aggressively solipsistic; perhaps what you’d get if Jorge Luis Borges had been born late enough to write about video games. It’s a sweeping exercise in formalism, about a sweeping exercise in formalism; that the title of the book and the eponymous white whale of a game its protagonist chases are the same seems unlikely to be either coincidence or even convenience.

Lucky Wander Boy is a novel about video games, but more, it’s a novel about granular, minute obsession; a desperate and all-consuming need to find or create meaning from meaninglessness. And so to write about Lucky Wander Boy is a somewhat reflexive exercise: it’s never quite clear—and probably never will be—where the line sits between the profound and the absurd. Does Lucky Wander Boy‘s density make it more rewarding? Or does it simply motivate readers to project profundity where none really exists? Pattern recognition is an intrinsic and hard-wired human trait; given no patterns to find, we will create them ourselves.


Superficially, Lucky Wander Boy is the story of Adam Pennyman, a man in his late twenties who has lied his way into a series of increasingly lackluster jobs; whose relationship—built on equally if less consciously disingenuous grounds—is falling apart. Pennyman channels his frustration and stasis into a growing obsession with classic video games, documenting and analyzing them obsessively in what he intends to be his magnum opus, the Catalogue of Obsolete Entertainments. To Pennyman, games are transcendent, almost supernatural; the catalogue entries where he hypothesizes connections between Donkey Kong and the demiurge of Gnostic heresies and reads Marx and Darwin into Pac-Man.


Back in the day, the GIA was notorious for its intricate and extensive April Fools’ pranks: massive site overhauls, fake announcements so painstakingly constructed that other sites regularly picked them up and ran them as actual news. So established was that reputation that when the GIA finally closed its doors on March 31, 2002, many readers assumed at first that it must be another such prank.

On April 1, 2000, among a bevy of other joke features, the GIA ran an exhaustive retrospective of the game Minesweeper. I don’t know if D. B. Weiss read the GIA; I do know that the Minesweeper vault, while somewhat more crude in its construction, predicts Pennyman’s Catalogue with almost uncanny accuracy.


Given the nature and structure of the novel—the intricate hall-of-mirrors strangeness, the genre self-awareness that borders on (but never quite slips into) satire, the first and most obvious approach to a Lucky Wander Boy retrospective would be as an entry in the Catalogue of Obsolete Entertainments.

(Is there a point at which layers of referentiality become so fine, so self-repeating that they become a seamless whole, merged under their collective weight and the pressure of authorial pretension like sedimentary rock? I assume there must be. It’s a thought that has followed me through this article; and before, through reading Pennyman’s vertiginous rhapsodies on the ghosts of numbers that flick across his emulated console, the book itself translated to the screen of my phone, far from the battered paperback I’d inherited near the end of college.)

Certainly, such an expansion of the scope of the Catalogue would not be without precedent: in the novel, Pennyman’s entries swell to encompass his job and, ultimately, himself. It would, of course, be one of the later entries, one of the ones that Pennyman writes as he slides further and further into obsession, myopically focused on the elusive Lucky Wander Boy and its elusive creator. In these entries, Pennyman’s tone dissolves from academic to personal as he claws desperately for meaning, some greater purpose or grand decision.

Adam Pennyman is not an appealing protagonist. He’s an unpleasant person. He lies. He’s manipulative, lazy, cruel; he doesn’t really seem to see other people as quite real. For me, at least, he’s also acutely relatable. For him, to interact with media is to lose himself in its minutiae; to try to hone some higher meaning from every errant pixel. But of course, what Pennyman is really searching for is his own reflection, the long-lost game that spoke his name and waits for him, and him alone. Aren’t we all?


“While the hedonistic treadmill carries the others through cycles of momentary appeasement and slow, scraping dissatisfaction, the geeks will penetrate deeper and deeper into the music the others cannot hear, its notes independent of the demands of the world that pull people through jobs and parties and bars toward their end. They will hear its forgotten strains and study its evolution in all its branching intricacy, and in the unlikely event of an afterlife they will have their music to carry them, they will never grow tired of it, they will still be going and going and going long after the others have overdosed on the maximum conceivable pleasure and chosen self-extinguishing over the ultimate boredom hangover that follows. Their passion is like a red dwarf star—it may not burn as hot, but it burns longer. It burns near forever.”

-D. B. Weiss, Lucky Wander Boy

For all its grounding in video games past, Lucky Wander Boy was in many ways a novel before its time. It’s easy to imagine it becoming a sensation in the world of ARGs and viral sensations, adopted by the same kids who revel in the open-ended complexity of Homestuck and spent hours dissecting Braid. Adam Pennyman’s minute, academically inflected approach to game criticism to some extent predicted the evolution of that field; his Confederacy of Dunces intractability, self-absorption, and fucked-up relationships with women predicted the culture that would grow around it.

In 2003, Lucky Wander Boy was an anomaly. It garnered positive if somewhat baffled reviews, achieved middlingly respectable sales, and fell rapidly out of print. It remains Weiss’s only published novel, and the rest of the works listed on his cursory Wikipedia entry are all adaptations or prequels for other franchises—most notably, the HBO adaptation of George R. R. Martin’s Game of Thrones.

And so the cult of Lucky Wander Boy has remained small. There’s instant camaraderie in finding another fan: you may not become bosom friends, but there will be some degree of mutual understanding. At best, you will find that you speak the same language of obsession and fetishize intricacy with the same fervor; at worst, they still probably won’t call you pretentious.

As I look back at the friendships I’ve formed over this book, it strikes me that they have involved almost no discussion of the book itself. The mutual acknowledgement is enough; the rest is either assumed to be universal or recognized to be personal to an extent that defies conversation.


“[The gamer is] skating across the surface of a chain of games, words, hopes, associations that has no endpoint. He has no existence save as this chain, this progression. He can choose to become two, three, four or more… but he cannot choose to stop choosing, because he is the choosing, the changing, the becoming.”

-D. B. Weiss, Lucky Wander Boy

The end of Lucky Wander Boy is—well, open is one word for it. Fractal. Fractured. A mirror-hall of choices. What meaning the reader is to derive from it, Weiss seems to tell us, is whatever meaning we’ve brought in. Pac-Man is a study in capitalist theory; Donkey Kong, a Foucaultian nightmare. Lucky Wander Boy—like the eponymous game—is whatever you create of it yourself.

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About the Author

is a writer and editor based in Portland, Oregon.



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