This study makes an analysis of I Know Why the Caged Bird Sings and Gather Together in My Name, two autobiographies by Maya Angelou and selected lyrics from the music of Tracy Chapman. Seeking to establish, comment and critique and perhaps interrogate the implications of resistance through “the word” in Maya Angelou’s works, it questions what this complex and creative use of literature and music means for the formulation of self-concepts and community identities. Conversely, it also foregrounds or assumes the presence of the themes of endurance, resistance, rebellion and protest in the two artists’ work. This is so as the two come from a background of deprivation, repression, violence, oppression and denigration as well as a silenced class. Maya Angelou and Tracy defy these odds and stand up to fight the injustices. In this sense, they are resisting racial and gender discrimination using various strategies of resistance. It interrogates what necessitated the resistance, and what they achieve in the end. In addition, it interrogates comments and even critiques the implications of this resistance to the self and the community as a whole.