Lucky Wander Boy tells the story of an obsessed collector of classic video games. Our protagonist has his childhood love of video games from the classic era reawakened by a coworker's copy of the MAME emulator and ultimately must choose what priorities to adopt in his life.
There has been a fair bit of discussion in recent years about the definition of the word "geek." One common definition holds that a geek is one who obsesses over some non-mainstream interest above all others. Weiss includes an essay (written from the perspective of protagonist Adam Pennyman) that defines the term to refer to one who places that non-mainstream interest above status. He argues that humans have a natural drive to be liked and respected, and that geeks are those in whom this drive is weaker than their personal obsessions.
Pennyman begins to write the "Catalogue of Obsolete Entertainments," an in-depth analysis of various vintage video games. Along the way, he finds himself employed at portal-entertainment.com, a media company involved in the production of a movie based on Lucky Wander Boy, a game that had been an important hobby during Pennyman's childhood.
Pennyman then feels compelled to fight his boss's attempts to turn the project into a low-quality action movie. He researches Lucky Wander Boy and its author and proceeds to write a script of his own, in hopes of delivering it directly to the author herself. Ultimately, he must choose between his geek need to save Lucky Wander Boy's cultural legacy and his human drive for a normal life and relationship with coworker and fellow classic game aficionado Clio.