Both clinical theory (Kernberg, 1974a) and diagnostic nomenclature (DSM-IV-TR; APA, 2000) describe narcissists as envious, although what little evidence exists suggests this relationship may be weak or nonexistent (Gold, 1996). To examine this discrepancy, 204 young adult students completed dispositional measures of narcissism (grandiose [adaptive, pathological] and vulnerable), entitlement, and envy. Later, students competed against ostensibly advantaged opponents in a betting simulation, completed self-report measures of relative deprivation and envy, and could spend some of their earnings to burn their opponents' earnings (assessing possible behavioural effects of envy). Structural equation models were evaluated for each episodic envy variant (self-reported, behavioral, indirect). Only the self-reported envy model demonstrated adequate fit and variance explained. Vulnerable narcissism strongly predicted envy via a "trait" route entailing susceptibility to chronic envy and a "triggered" route implicating frustrated entitlements, whereas adaptive narcissism predicted envy via the "triggered" route only. Possible theoretical and clinical implications are discussed.