Despite envy’s importance as a driver of social behavior, scholars disagree on its conceptualization. We review the literature and distinguish three incongruent theories: (a) Malicious Envy Theory (i.e., envy as uniform and malicious), (b) Dual Envy Theory (i.e., envy as taking on 2 forms, benign and malicious), and (c) Pain Theory of Envy (i.e., envy as uniform and driven by pain). Moreover, within and across theories, operationalizations of envy have included various different components. We integrate these conceptualizations using a data-driven approach, deriving a comprehensive theory of envy in 5 studies (total N = 1,237)—the Pain-driven Dual Envy (PaDE) Theory. Exploratory and confirmatory factor analyses of an exhaustive set of envy components (Studies 1–4) suggest that envy consists of 3 factors: Pain (i.e., preoccupation with the envy-eliciting situation, inferiority), predicts both benign envy (i.e., desire for the envy object, improvement motivation, emulation of the other), and malicious envy (i.e., communication about the other, directed aggression, nondirected aggression). An experience-sampling study (Study 5) suggests that pain constitutes a quickly fading reaction, whereas benign and malicious envy are enduring attitudinal constructs. We apply this theory in a meta-analysis on the controversial relation of envy and schadenfreude (N = 4,366), finding that envy and schadenfreude are more strongly and positively correlated to the extent that the respective research operationalizes envy as malicious, compared with as pain or benign envy. We discuss how the PaDE Theory can illuminate research on envy in diverse settings, and envy’s relation to other distinct emotions.