This paper compares the attitudes towards life of the iconoclastic literati of the Wei and Jin dynasties (namely Ruan Ji 阮籍 and Ji Kang 嵇康) and Cao Xueqin 曹雪芹 (or Jia Baoyu 賈寶玉, his voice in the Dream of the Red Chamber 紅樓夢). In the first section, we discuss anti-Confucianiasm ad anti-moarchism and how the iconoclastic literati of the Wei and Jin objected to empty ritualism and Confucianism being turned into a vehicle for slaughter in the hands of the ruling class (Ji Kang, for instnce, placed himself above social strictures and followed nature while Ruan Ji proposed a kingless society). For his part, Cao expressed similar ideas in The Dream of the Red Chamber in making no distinction between high and low, superior and inferior. The next section looks at the great importance attached to sentiment 情 by these literati. Ruan was well known for his expression of true love and deep affection, while Jia Baoyu breaks through the limits and controls the ethical relations to express his love for not only youg maids but also all living things. Finally, we focus on a sense of mourning over the passage of time that is a fundamental theme of Ruan's yunghuai 詠懷 (expressing the feelings of the heart) poems and attempts by the iconoclastic literati of the period to summon up the past and preserve memories in their writing in an effort to combat the passage of time and a coming death. We find similiar thems and creative motifs in The Dream of the Red Chamber and note that Cao lets Baoyu live in the Daguan Garden 大觀園 because a retreat to such garden is reminiscent of the ideal life-style of those iconoclastic literati.