Henry Darger is typically thought of as the archetypal, reclusive Outsider artist. The Chicago artist, who lived from 1892-1973, was orphaned as a child and spent most of his adult life as a janitor for various hospitals. Having severely limited contact with the outside world, he created, in his off-work hours, an exquisitely detailed and complex fantasy world called In the Realms of the Unreal, which was discovered posthumously. Along with the text he composed hundreds of illustrations, which are also autonomous works of art in their own right. Acknowledging his current Outsider status, I ask the question, how much of an outsider was Henry Darger, really? This thesis recontextualizes the work of Darger in a new context, that of early twentieth-century hobby culture. Observing the ways in which his artistic practice reflects a potential link to hobby culture, through its use of models, templates, and production, I seek to assert Darger's place in a larger community. In addition, I tie recurring themes in his text and drawings with contemporary popular literature, such as L. Frank Baum's Oz series and Harriet Beecher Stowe's Uncle Tom's Cabin. Finally I examine the ways in which this leisure culture reinforces productive work models, bringing a certain work-like practice into the home. The hobby can also be viewed in the context of Darger's art as a kind of self-management or self-regulation. Pushing the limits of hobbydom to the extreme, Darger puts on display the productive ideology of American hobby culture, and consequently, his critical potential as an artist.