In this article, we test psychodynamic assumptions about envy and narcissism by examining malicious envy in the context of narcissistic grandiosity and vulnerability. In Study 1, students (N = 192) and community adults (N = 161) completed trait measures of narcissism, envy, and schadenfreude. In Study 2 (N = 121), participants relived an episode of envy, and cognitive-affective components of envy were examined in the context of both self- and informant reports of their envy and narcissism. In Study 3 (N = 69), narcissism was linked to reports of envy covertly induced in the laboratory. Vulnerable narcissism was strongly and consistently related to dispositional envy and schadenfreude (Studies 1–2), as well as to all cognitive-affective components of envy (Study 2). Furthermore, it facilitated envy and schadenfreude toward a high-status peer (Study 3). Grandiose narcissism was slightly negatively related to dispositional envy (Studies 1–2), and it did not predict informant reports of envy or cognitive-affective components of the emotion (Study 2). Finally, it did not exacerbate envy, hostility, or resentment toward a high-status peer (Study 3). The results suggest envy is a central emotion in the lives of those with narcissistic vulnerability and imply that envy should be reconsidered as a symptom accompanying grandiose features in the diagnosis of narcissistic personality disorder.