Chen Yingzhen has been regarded as the Taiwan’s utmost representative leftist intellectual. However, this article tries to reconstruct Chen’s historical significance in Taiwan’s Sixties in a broader perspective. Taiwan’s Sixties was a peculiar period. While there was a global youth rebellion, Taiwan’s post-war baby boom generation, who have just been re-educated as Chinese, were going through a cultural “renaissance” and started to practice what they have digested, and to realize their creativities in all aspects, and this could be called the generation’s self-realization. Chen Yingzhen was one of their initiator and leader, and a very significant one. The fact that there were no dominating ideologies during this period allowed room for this wave of creativity to flourish.