Sisyphus myth is the paradigm of a meaningless life with the features of pointlessness and futility. He is condemned to roll a huge stone to the top of a hill in the underworld. Upon reaching the top, the stone immediately rolls down to the bottom and thus he must repeat the labor endlessly. Pathetic as his eternal punishment is, it reflects the fundamental question of life meaning and thus evokes nonstop philosophical discussions and literary interpretations. This study aims to examine this timeless myth through the Buddhist perspective. Sisyphus’ endless task of stone rolling represents a samsaric existence deprived of freedom and autonomy. Yet, there exists the hope of liberation in the bondage of repetitious labor. The contents of this study are divided into two parts. The first part analyzes Sisyphus myth as a manifestation of samsara and karma. The second part provides his predicament with the solution of Zen insight. While Sisyphus myth is generally recognized as a metaphor of existential absurdity, Dharma offers the spiritual remedy to give the seemingly doomed karmic recompense a positive twist.