Music mood recognition by machine continues to attract attention from both academia and industry. This thesis explores the hypothesis that the music emotion problem is circular, and is a primary step in determining the efficacy of circular regression as a machine learning method for automatic music mood recognition. This hypothesis is tested through experiments conducted using instances of the two commonly accepted models of affect used in machine learning (categorical and two-dimensional), as well as on an original circular model proposed by the author. Polygonal approximations of circular regression are proposed as a practical way to investigate whether the circularity of the annotations can be exploited. An original dataset assembled and annotated for the models is also presented. Next, the architecture and implementation choices of all three models are given, with an emphasis on the new polygonal approximations of circular regression. Experiments with different polygons demonstrate consistent and in some cases significant improvements over the categorical model on a dataset containing ambiguous extracts (ones for which the human annotators did not fully agree upon). Through a comprehensive analysis of the results, errors and inconsistencies observed, evidence is provided that mood recognition can be improved if approached as a circular problem. Finally, a proposed multi-tagging strategy based on the circular predictions is put forward as a pragmatic method to automatically annotate music based on the circular model. / Graduate / 0984 / 0800 / 0413 / zazz101@hotmail.com