Creative industries produce many one-hit wonders who struggle to repeat their initial success and fewer hit makers who sustain success over time. To develop theory on the role of creativity in driving sustained market success, I propose a path dependence theory of creators’ careers that considers creators’ whole portfolios of products over time and how their early portfolios shape their later capacity to sustain success. The main idea is that a creator’s path to sustained success depends on the creativity in their portfolio at the time of their initial hit—relatively creative portfolios give creators more options for leveraging their past portfolios while adapting to market changes, increasing their odds of additional hits. I tested the proposed theory using an archival study of the U.S. music industry from 1959–2010, including data on over 3 million songs by 69,050 artists, and the results largely support the hypotheses. Artists who reached their initial hits with relatively creative (novel or varied) portfolios were more likely to generate additional hits, but a novel portfolio was less likely to yield an initial hit than was a typical portfolio. These findings suggest that new creators face a tradeoff between their likelihood of initial versus sustained success, such that building a relatively creative early portfolio is a risky bet that can make or break a creator’s career.