This study focuses on the award-winning artworks of Western Painting in Joseon Art Exhibition of ‘the artists who defected to North Korea(Wolbuk Artist)’ who was active in the period of Japanese colonialism. Most of Wolbuk artists were developing their views on art in their late teens and early 20s and made their debut to the art world through Joseon Art Exhibition. Therefore a study on the award-winning paintings of Wolbuk artists in Joseon Art Exhibition will provide an opportunity to research their early paintings and training processes, and development of their views on art. The study focuses on finding activities and tracks of the artists who were neglected and not even mentioned due to their defection to North Korea. In order to do that, I looked for 'Wolbuk artists and their painting sin A Biographical dictionary of artists in Joseon (revised edition) written by Lee Jae-hyun which published in North Korea. From this book, I made a list of 96 paintings of 24 artists who won more than once in the Western Painting Department in Joseon Art Exhibition. Based on their first time award-winning paintings in Joseon Art Exhibition, the art activities of these 24 artists were divided into 4 groups -the 1920s, the early 1930s, the late 1930s self-taught, and the late 1930s study-abroad in accordance with the period of their activities and learning types. The winners of Joseon Art Exhibition in 1920s, Kim Yong-jun, Kim Joo-kyeung, Kil Jinsub, Jung Hyun-woong are well-known Wolbuk artists. Except Jung Hyun-woong who was selftaught and active artist in Joseon Art Exhibition, the rest received their basic education on painting in Koryu Art Institution and were educated with ideology of socialism in their years of high school and Tokyo National School of Fine Arts. To express their ideology/philosophy of art, they preferred to be active in group exhibitions than in Joseon Art Exhibition. These four artists including Jung Hyun-woong shared much in common for that they were crossing boundaries of art such as publishing and education during the late 1930s.