This paper aims at researching Fabulation or The Re-education of Undine by Lynn Nottage which shows social insight with sarcastic perspectives and comic inversion in a “far less predictable” way. As a third generation of African American woman playwright, Nottage who gained prestige attached to the Pulitzer Prize award in 2009 deals with social issues by suggesting a civic character Undine and foregrounding a raised issue of the inner conflict between middle and lower class in African American community. She denies the label and the categorization of African American plays by ancestors and shows ‘flexibility’ and ‘mobility’ beyond the racial issues. In Fabulation, Nottage explores intensified stratification among the classes in African American community by introducing a dramatic rise and fall of Sharona Wilkens who changes her name to Undine Calles to achieve the top position in elite business field. Undine amplifies a new issue revolving around the growing population of upper/middle class in African American community. Nottage foregrounds the “unspoken issue” in the community by high lightening the duality of a CEO Undine as a ‘top girl’ in business as well as a welfare queen in Brooklyn. In the process of Undine’s tumbling from top to bottom and her re-education, Nottage exposes the alienation of a African American family as well as the irrational social welfare system of the U.S. government. Fabulation signifies the future aspects of African American plays, escaping from the color-coded prison and opens a new era of African American women’s theater marching to the mainstream stage regardless of sex, race, and class.