In the present chapter, we present the case study of the only woman film director who has ever won an Academy Award for Best Director, Kathryn Bigelow. We analyzed 43 written interviews of Kathryn Bigelow that have appeared in the popular press in the period 1988–2013 and outlined eight main themes emerging regarding her exercise of leadership in the cinematic context. We utilize three theoretical frameworks: (a) paradoxical leadership theory (Lewis, Andriopoulos, & Smith, 2014; Smith & Lewis, 2012); (b) ambidextrous leadership theory (Rosing, Frese, & Bausch, 2011), and (c) role congruity theory (Eagley & Karau, 2002) and show how Bigelow, as a woman artist/leader working in a complex organizational system that emphasizes radical innovation, exercised paradoxical and ambidextrous leadership and challenged existing conventions about genre, gender, and leadership. The case study implications for teaching and practice are discussed.

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