Although many studies have examined individual difference predictors of cheating, insufficient attention has been given to several important personality variables (the Big Five, perfectionism, and subclinical psychopathy). Moreover, insufficient use has been made of concrete indicators of naturalistic scholastic cheating. Using a computer-based behavioral measure, we examined the correlates of multiple-choice exam cheating in several large undergraduate classes. In Study 1, 291 participants completed a comprehensive battery of personality measures. Their cheating on several subsequent exams was best predicted by their level of subclinical psychopathy. A possible artifact is that those high in subclinical psychopathy are less scholastically competent—a factor known to predispose cheating. To address this possibility in Study 2 (N =150), we included measures of cognitive ability and a pre-course knowledge test. After controlling for both ability and prior knowledge, subclinical psychopathy remained a significant predictor of cheating behavior. Demographic variables such as gender, ethnicity and major did not add significantly to the prediction of cheating. Implications for educators and researchers of cheating are discussed.