Much like the Harlem Renaissance in the 1920s, which established the vitality and relevance of Black artists to an international audience, the Chicago Literary Renaissance, of which Masters was a leading voice, defined the importance and relevance of Midwestern life in America. For more than 10 years leading up to World War One, a gathering of writers, artists, playwrights, journalists, composers, and photographers dedicated themselves to capturing the realities of life in a Midwestern culture being compelled to abandon its rural roots and find an entirely new identity within an urban environment.

The movement had its initial conception around 1893 when Chicago hosted an international exposition to commemorate the anniversary of the voyages of Columbus. For months, intelligentsia from around the world flocked to Chicago, and in the process resident artists began to perceive the changing nature of the Midwest. Working against the idealistic stereotype of a bucolic rural world whose residents maintained a strong work ethic, clear family identities, and stabilizing religious grounding, the members of the emerging Chicago Renaissance were determined to reveal a more honest definition of the peoples and cultures of the changing Midwest.