This paper discusses Tang Hsien-tsu’s (湯顯祖) self-transition, his changing relationship with the world, and his deepened inclination to introspection after his fall from grace in 1591. This paper takes 1591 as a turning point in Tang’s life and thought, presenting Tang’s removal from his official position as a possible reason for the timing of Tang’s peak period of playwriting. After Tang was removed from his official position, he used playwriting to express his feelings. In his plays, Tang allowed his imagination full reign without boundaries. His most mature works—“The Peony Pavilion” (牡丹亭), “Nan-k’o Chi” (南柯記), and “Han-tan Chi” (邯鄲記)—were collectively composed after 1591, when Tang returned to his hometown. The key theme in these three plays is “ch’ing” ( 情); moreover, the main characters in all three plays sought to understand themselves. Tang’s plays were not written purely for amusement, but rather offered him the chance to explore and observe “reality.”