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This study aims at investigating the effect of corporate social responsibility (CSR) and corporate social irresponsibility (CSI) on corporate financial performance (CFP) in firms headquartered in developed versus emerging countries. Drawing upon stakeholder and legitimacy perspectives, the authors argue that the CSR/CSI–CFP relationship differs depending on the home-countries’ level of economic development as this reflects their different sensitivity to sustainability. Indeed, as emerging economies are normally characterized by weaker regulations, they are likely to place lower pressures on companies for superior CSR practices. Therefore, the authors expect the effect of CSR on CFP to be more positive for firms headquartered in advanced than in emerging countries. At the same time, the authors propose a more negative relationship between CSI and CFP for firms headquartered in developed countries due to the higher overall sustainability expectations required to gain legitimacy. The empirical analyses, run on a sample of 1,971 publicly listed firms between 2010 and 2020 from developed and emerging economies, support the expectations, thus confirming that country-specific contextual factors do play a role in shaping both the positive and the negative impact of CSR and CSI on CFP, and that the reactions of stakeholders to responsible and irresponsible behavior are stronger when their sensitivity to sustainability is higher.