The words "individuality" and "creativity" have been frequently used in the philosophy of Japanese education since the Meiji period, and emphasis on individuality has come to be a key term in recent educational reforms. However there is no consensus on how these words are understood by teachers, administrators and scholars. This study analyzes how individuality and creativity are understood, taught and evaluated in Japanese and American classrooms, by focusing on language arts lessons, and in particular writing instructions. Observation of lessons, interviews with teachers, and analysis of students' compositions reveal that in American classrooms, creativity is achieved through ideas written in realistic terms in an appropriate form, whereas in Japanese classrooms, it is achieved through vivid expressions of personal feelings based on the shared experiences of a teacher and fellow students. In order to achieve creativity, teachers in the United States give strict guidance in composition, stressing techniques for choosing the style best fitting the student's individual objective among several different ones. In Japan, teachers encourage students to freely express their feelings, and yet students' compositions show remarkable similarity. Paradoxically, the strict technical teaching of different styles produces variety in students' writing in the United States, while the encouragement of free writing produces compositions that are strikingly similar to each other in Japan. One of the reasons of this outcome is that mastering different styles provides a choice among alternatives for American students to express their ideas. However, the results of the research do not mean that Japanese students lack individuality and creativity. Rather, differences in American and Japanese teachers' views of "individualtiy" and "creativity" influence teaching practices and their outcomes.