The authors begin this article looking at the start of the journey through this new 21st century and how educators at every level are endeavoring to meet the challenge to be responsive to the educational needs of their students, current and future. This is especially true in relationship to the education of students of diverse backgrounds (Ladson-Billings 2001; 1999; 1994) in public educational settings. They first discuss cultural identity and cultural experience, then articulate their meanings for cultural identity, cultural experience(s), and cultural gap in the context of this work. Next, the authors address two questions: (1) In what ways does critical race theory (CRT)/critical race feminism (CRF) connect with issues of cultural identity and cultural experience and (2) in what ways have such connections served the praxis of two African American educators?