Grounded in stakeholder theory and a resource-based view of the firm, this longitudinal research demonstrates the evolution of corporate social responsibility (CSR) and firm reputation over time. Drawing on a 5-year sample of 285 major U.S. firms obtained from the KLD database and Fortune’s Most Admired Companies, we find that the proposed dynamic relationship predicts evolving stakeholder expectations to incite organizations to improve their social performance to earn reputational benefits. Contrary to the often labeled stickiness of reputation, we find a "Red Queen" effect that supports reputation as a dynamic construct where the change in CSR does predict a change in corporate reputation. Similarly, we find that the change in reputation over time varies by industry, being most pronounced for manufacturing. From a practical perspective, this relationship across time may incite managers to create sustainable competitive advantage by continuously investing in doing good to reap the benefits of looking good and looking even better with time.