Organizational life is rife with opportunities for social comparison. Although the status and performance of an employee might be objectively high by most standards, the relative standing of that employee compared to other employees might result in feelings of envy. Especially upward pay comparisons with those earning more than oneself, can result in benign or malicious envy. Building upon social comparison theory, we investigated whether high or low assimilation with an upward comparison person is associated with malicious and benign envy, so that envy is dependent upon the degree of assimilation. We also examined whether individual differences in core self-evaluation and social comparison orientation moderate the association between upward pay comparison and malicious and benign envy. For this study, we designed a randomized vignette study manipulating assimilation with the upward comparison person, followed by a survey measuring the dependent variables. 462 full-time employees were recruited using an online data collection platform. Contrary to our hypotheses, the findings did not support the expected associations. However, the findings suggest that individuals’ self-evaluations and their tendency to compare themselves with others may play a role in their experiences of envy. Further research is necessary to determine the relationship between assimilation with a comparison target and malicious and benign envy, to investigate when and why some upward pay comparison processes lead to favorable, and some to unfavorable, employee and organizational outcomes.