This article offers a comparative study of the strategies employed by Will Smith (together with his partner James Lassiter) and Tyler Perry as they surmounted racial barriers to become two of the most successful people in film. What emerges in both cases-despite very different institutional, production, and marketing strategies-is that race has strongly determined the career development of black top talent. Racial hierarchies have presented various obstacles hindering the progress of these individuals, but more surprisingly, such hierarchies have also indirectly facilitated their success. They were seized on by Smith, Lassiter, and Perry as both impetus and opportunity. The final section turns to a consideration of the racial implications of their breaking into film's elite ranks, suggesting that neither the racially incorporative nor resistive dimensions of this achievement have been sufficiently considered. © 2013 Copyright Published with license by Taylor & Francis.