Since the publication of Their Eyes Were Watching God in 1937, African American women authors, consciously or subconsciously, have re-imagined Zora Neale Hurston’s Janie Mae Crawford character in various settings with conflicts pertinent to their respective era. Hurston’s Janie is an archetype for African American women characters who are involved in quest fiction. Janie’s primary objective is to experience romantic love and sexual expression. During her quests she combats intense influences in her life that threaten to ruin her dream, influences such as her Nanny’s Victorian principles of respectability and loveless marriages. Despite her struggles, Janie is successful in her quest; therefore, she is a self-actualized character. A guiding question for this project is what becomes of Hurston’s once-self-actualized Janie? I address this question by examining Ann Petry’s The Street (1946), and Sister Souljah’s The Coldest Winter Ever (1999) and A Deeper Love Inside: The Porsche Santiaga Story (2012). These three texts by African American authors each feature a Black woman protagonist at the helm of the story. I read the main women characters as literary reiterations of Archetypal Janie. Petry’s and Souljah’s texts, which span more than eight decades, and emphasize realistic social, cultural and political issues, can be read as modernized versions of Archetypal Janie’s quest story. This project does the following through literary and cultural analyses: 1) provides background on and justification for the pairing of street literature with canonical texts; 2) establishes a “Self-Actualized Janie” or a “Tragic Janie” as the two particular categories for Black women characters since Hurston’s Janie; 3) analyzes the internal and external factors that contribute to the character’s self-actualization or tragic outcome; and 4) emphasizes the importance of community and ancestral guides to the character’s development and actualization.