Popular theorizing about happiness pursuit emphasizes universal paths to happiness, but other theorizing acknowledges different people achieve happiness in different ways (i.e., subjective well-being, SWB). The present work extended this latter perspective by examining how antagonistic pursuit of a grandiose identity ('narcissistic antagonism') - generally thought to reduce narcissistic people's SWB - may relate to increased cognitive well-being (i.e., a component of SWB) for narcissistic people with lower self-esteem. In Study 1, participants (N = 417) reported their narcissism, self-esteem, narcissistic antagonism, and general life satisfaction (to index cognitive well-being). In Study 2 (pre-registered), participants (N = 450) reported their narcissism, self-esteem, narcissistic antagonism, general and domain-specific life satisfaction, and general affect (to index affective well-being, which is a different component of SWB). Both studies revealed narcissistic antagonism related to increased life satisfaction only for more (vs. less) narcissistic people with lower (vs. higher) self-esteem. Study 2 not only replicated this interactive pattern on satisfaction across various life domains but also revealed the interaction may be related to increased negative affect. Broadly, results highlight how different people may enhance features of SWB in different, even 'dark', ways. © 2020 British Psychological Society.