High school curriculum reform involves many complicated issues. This study aims to discuss the challenges of high school curriculum reform by addressing the curriculum issues reflected in the Eight-Year Study, the well-known educational experiment conducted in the United States from 1930s to 1940s. Firstly, the authors review the historical significance of the experimental curriculum and the recommendations rendered by the Progressive Education Association at the end of the experiment. Then, this study discusses the issues involved in the implementation of the experimental curriculum in the Eight-Year Study. Additionally, the authors offer some critical reflections to rethink the curriculum experiment experience of the Eight-Year Study. Finally, this study addresses the implications of the issues and recommendations for the current high school curriculum reform in Taiwan. It is hoped that through the review of the historical curriculum events, this paper can provide different perspectives for more thoughtful deliberation in the policy making of the current high school curriculum reform.