In his hard-boiled detective fiction series set in Harlem, Chester Himes created a wide variety of recurring African American female character types. In this essay, I focus on The Crazy Kill (1959/1989), assessing the extremely ambitious, sexually alluring, scheming, and manipulative outlaw female characters. Himes's novels suggest that viewing these female characters as merely immoral or unethical is too simplistic. Context, history, traditions, political, and socioeconomic imperatives count. However, because of genre expectations established for more than 100 years, an assertive female character may be overly determined as merely a femme fatale. Also, because of traditions established depicting African American female characters as wanton, overly sexualized beings, the expectation that a racialized female character is morally objectionable is rooted more in racism than in evidence of the character's conduct. I suggest Himes challenges traditional expectations established by the genre for female characters as well as time-honored popular culture depictions of racialized characters, by offering an affirming critical read of his ambitious Harlem female characters.