Prior literature on humor primarily documents its positive effects on employees’ attitudes and behaviors, though increasing research on aggressive humor suggests some conflicting viewpoints. This paper proposes a model based on social comparison and attribution theories to examine the influence of supervisors’ aggressive humor on employees’ strain and addictive behaviors. The tests of the research model entailed a 2-wave study with 243 frontline employees from 4 manufacturing companies of a group corporation in China. The results showed that supervisors’ aggressive humor with employees related positively to employees’ strain. This positive association became stronger when the supervisors did not use aggressive humor with the peers of the focal employees. Employees’ strain mediated the interactive effects of supervisors’ aggressive humor with the focal employees and those with their peers on employees’ addictive behaviors (e.g., problematic use of Internet, alcohol, and tobacco). As well as having practical implications, this study offers theoretical insights for research into humor, leadership, and addictive behaviors.