Using Vietnam’s legends of “principal graduates of the two kingdoms,” I introduce a concept of “civilization envy.” A principal graduate was one who scored the highest in imperial examination, and the two kingdoms referred to Southern Kingdom (today’s Vietnam) and Northern Kingdom (today’s China), respectively. Civilization envy was a mentality that desired to prove one’s civilizational equity with or even superiority over the center of All-Under-Heaven, namely, China. This mentality was common in historical East Asia (including China), especially among literati. It manifested differently in East Asia, and among its various Vietnamese manifestations, these legends conveyed it in the most pronounced way. They all share a motif of “underdog’s triumph.” The stories relate an arrogant Chinese emperor picking up on a Vietnamese envoy and conjuring up vicious tricks to expose his supposed lack of civilization, only to be awestruck by the envoy’s extraordinary literary talent. The emperor is so impressed that after his failed plea for the envoy’s stay, he bestows on him the honorific title and sends him home. The earliest legend was written in the 18th century, and over time the stories of five such principal graduates appear, and their stories are taught in modern Vietnam. In this talk, I will chart the evolution of these legends to illustrate the mentality of civilization envy. I will also compare it with “grammar envy,” a concept coined by Sanskrit Philologist Sheldon Pollock, so as to highlight how entrenched the cultural-geopolitical metaphor of “the center” is in East Asian history.