One of the four most celebrated talents of Wu (Suzhou) from the Ming dynasty, Zhu Yunming (1461-1527) was most admired for his accomplishment in calligraphy. At a time when the leading trend in the late Ming dynasty was artistic freedom and liberation from rules in calligraphy, Zhu Yunming was ranked the period's finest calligrapher and leading proponent of this trend-being the first to revolutionize the cursive script. Here, my research establishes and classifies Zhu Yunming's achievements in the various styles of writing as a basis for judging his style of calligraphy. His background, philosophy, and influence on the literati style of Suzhou (national, economic, cultural, and commercial centre) during the Ming Dynasty will also be highlighted according to his three stages of artistic development. Zhu Yunming thrived on variety and change and was renowned most notably for his iconoclastic thinking. At the pinnacle of his art, we see the calligrapher - one who was not only well-versed in the scripts of several great ancient masters, but also able to synergize these forms to craft his unique style of the cursive script.