This paper aims at exploring the influence of corporate social responsibility (CSR) on firm performance and brand value for the companies covered within the top list of 50 U.S. companies for Social Responsibility drawn up by the Boston College Center for Corporate Citizenship and Reputation Institute, over the period 2008-2011. Moreover, this paper attempts to relate CSR with entrepreneurship, respectively Corporate Social Entrepreneurship and Corporate Entrepreneurship. Firm performance was measured both through accounting-based (return on assets and return on equity) and market-based firm performance measures (earnings per share). Brand value was proxied through Brand Finance data. CSR was reflected through the index developed by Carroll School of Management’s Center for Corporate Citizenship at Boston College in conjunction with the Reputation Institute. By employing panel data regression models, there resulted a positive and statistically significant relationship between CSR and firm performance as proxied by return on assets. However, we notice the lack of any statistically significant relationships between CSR and return on equity, as well as CSR and earnings per share. Furthermore, there was found no association between CSR and brand value.