Na Hye-sŏk (1896–1948) was a feminist writer during Korea’s colonial period, an outspoken advocate of equal rights for women, and Korea’s first woman painter of Western-style painting. As a prolific painter of landscape in oil color, Na produced over three hundred paintings and won several times at the Chosŏn Art Exhibitions. However, after her divorce following an extramarital love affair, this talented and envied “new woman” lost her celebrity, lover, children, and career and died alone in a hospital for vagrants. Both admired and vilified when alive, in the late 1990s Na was rehabilitated by scholars of Korean literature, art history, and women’s studies, and finally by the Korean government itself. This chapter attempts to elucidate this intriguing figure and her recent cultural comeback and finds a woman of remarkable originality, ability, and determination, with a passion for painting and writing that made her an icon in her time. It also shows that the trajectory of Na Hye-sŏk’s life and career was largely determined by the men in her life and by the constraints of public expectations of women. Fifty years after her death, her “re-iconification” arose from a confluence of three forces—influential men, feminism, and politics.