Women face significant hurdles in the attainment of leadership positions. When they do attain them such positions tend to be riskier than those attained by men, a form of bias called glass cliff. This study investigates ambivalent sexism as an individual difference that influences the occurrence of glass cliff. Little research examines individual differences contributing to glass cliff. It is proposed that individuals with high hostile and benevolent sexism are more likely to perceive women to be suitable for leadership of a poorly-performing organization and men to be suitable for leadership of a well-performing organization. The sample of our experimental study consisted of 378 students who rated either a female or a male candidate under a poor or good performance condition. We tested our hypotheses using a moderated regression analysis. Both components of sexism impacted how individuals evaluated male and female leaders under different organizational performance conditions. Hostile sexism was the dimension that led to glass cliff. Benevolent sexism had an unexpected effect on leadership choice. The differences between the two types of sexism and the different role each type plays in preference for masculine and feminine leadership are discussed. Leader gender and perceiver's sexist attitudes influence evaluations for leadership positions.