The choice for a particular narrative architecture has been a major concern for the literary writer and to the African American literary writer, the use of African oral literary elements has been a resourceful option. The present study hypothesizes that August Wilson uses the dilemma tale as a narrative architecture in his The Piano Lesson play and argues that this narrative style helps Wilson to frame the dialogic surrounding what legacy is to the African American. The study reveals that tradition is problematic for the African American to conceive. The conclusion is that the dilemma tale type as a narrative style helps to understand that tradition or, legacy is a complex phenomenon for the African American to fathom.