Using data from a representative sample of adults age eighteen to fifty-five who reside in Toronto, Canada, and are employed in the paid labor force, this study asks: Are the health benefits of education, income, job autonomy, and nonroutinized work different for women and men? If so, do mastery and self-esteem contribute to those differences? Results show that women and men derive different personal benefits from socioeconomic status and job qualities: (1) education, job autonomy, and nonroutinized work are associated more positively with the sense of mastery among women, (2) job autonomy is associated more positively with self-esteem among women, (3) education, job autonomy, and nonroutinized work are associated more negatively with depressive symptoms among women, and (4) job autonomy and nonroutinized work are associated more positively with global health among women. Moreover, the patterns in (1) and (2) explain the gender-contingent effects in (3) and (4). In addition, unexpected suppression effects reveal that, among men, education is associated negatively with mastery and self-esteem-but only after adjustment for job conditions. I interpret the findings in the context of the disadvantaged status thesis and speculate about status-related social comparison processes.