D.B. Weiss says he inoculated his sense of humor against the “sometimes stifling MFA atmosphere” he encountered at the Iowa Writers’ Workshop by hitting Trinity College in Dublin for a master’s in philosophy first. “I don’t remember much of that, but I’ve been told I had a great time,” he says. “When else am I going to have the time and the liquor necessary to read Finnegans Wake from cover to cover?”

Weiss, who was born and raised in Chicago but now lives in Los Angeles, says there are funny people in writing workshops, but it’s hard to discuss techniques as slippery as humor, so students are afraid to share “nonserious” writing. “Humor–the kind that draws a laugh, not a knowing smirk–sometimes has to swing for the fence, and if you strike out hard, or even if you strike out with half the people…well, it can make for an uncomfortable writing workshop situation.”

In Weiss’s first novel, the wry Lucky Wander Boy, which was published in February by Plume, young narrator Adam Pennyman fakes his way into a job as an Internet copywriter after getting fired from another where he was pretending to be a graphic designer. Bored with the stupid porn sites, bad movies, and other philistine modern amusements he has to promote, he devotes his free time to a somber cause: the compilation of something he calls “The Catalog of Obsolete Entertainments,” a book-length series of essays offering analyses of arcade games from the golden era of Pac-Man and Donkey Kong that would sound laughably self-important and academic even if they were written about King Lear. During his research he hears mention of one of his forgotten obsessions: Lucky Wander Boy, a failed absurdist video game in which there’s apparently no way to win; after a certain stage the player simply wanders in the desert. Pennyman proceeds to lose his marbles trying to find an old machine.

The action and dialogue are flush with slapstick and wit, and at first it’s easy to snicker at Pennyman’s stuffy prose. But as his search for a Lucky Wander Boy console takes over his life–two beautiful girlfriends in turn throw up their hands at him, and he loses his grip at work–the catalog becomes frantic, personal, and philosophically resonant.

Pennyman’s fascination with the decadent ease of home video game systems–suddenly players could move from one video world to the next by reaching down from the couch to switch cartridges instead of walking from one arcade machine to another–is key to his worldview. His narrator, says Weiss, is profoundly dissatisfied with having only one life to live, a mentality that comes from video games, “but could just as easily come from TV or the Internet or many other places–an attitude that initially has an ‘eat your cake and have it too’ allure to it, but ends up paralyzing him by leaving him unable to make concrete choices.” The novel’s ambiguous ending, he says, “is where this character flaw begins to infect the very story he’s telling us.”

Weiss says he keeps his own writing under control by being honest with himself about his chops. “With my own work at this point in time, I think I’d rather have ‘serious’ working as an undertone or an aftertaste, something that occurs to you after you’re done reading it, rather than in the middle, or on the first page. I’m just not a very ‘serious’ person, and I think that when people who aren’t serious–and good at it–try to go for it anyway for whatever reason, the results are hardly ever readable.”

When Pennyman interviews for the copywriting job, he can’t name any fiction projects of his own to back his claim that he’s a writer–but he gets it anyway because the boss assumes his experience is all in advertising and is relieved, thinking the new employee won’t steal company time for his own work. Weiss has often feared he isn’t a real writer himself. “It’s a very tenuous thing,” he says. “Some days it seems like it’s all going so well–and then you remember that thing you did a few months ago that seemed like it was going so well, that somehow turned into an absolute piece of shit while it sat on your hard drive. But the impostor complex waned a little bit after Lucky Wander Boy came out. I mean, I still like it, and it’s been more than a year since I wrote most of it.”

Weiss will read from Lucky Wander Boy at 8 PM on Friday, April 18, at Quimby’s 1854 W. North, 773-342-0910. It’s free.

Art accompanying story in printed newspaper (not available in this archive): photo/Paul L. Merideth.