At the age of seventeen, he took an exam. As far as literary talent is concerned, he was absolutely the first, but because of his poor handwriting, the examiner ranked him as the second. This incident greatly stimulated Dong Qichang. From then on, he studied calligraphy seriously and made considerable achievements. His representative works include Pipa Xing by Bai Juyi, Poems of Haicheng, Destiny of Three Nobles, Poems in Cursive Script, Overlapping Pictures and Postscripts, Ni Kuanzan, Fu Ji before and after the Red Wall, etc. Dong Qichang put forward the theory of "North-South School" in view of China's traditional literati painting creation, which contributed to the sectarian dispute in painting and had a great negative impact. His calligraphy and painting creation advocates development and innovation on the basis of copying the works of the ancients, and pursues maturity before beauty in the use of pen and ink, which embodies the simple and naive personality of literati's creation. Coupled with his prominent political position at that time, his style of painting and calligraphy became the mainstream of the painting circle in Ming Dynasty, including Essays on Painting Zen Room, Rong Tai Collection and Painting Purpose. Dong Qichang is also involved in painting. He is good at painting landscape paintings and studied under Dong Yuan, Huang. His painting style is leisurely and gentle, fresh and beautiful, simple and elegant.
His landscape works are softer, more attractive, less bold and less imposing. He advocated imitating the ancients rather than creating them, such as "Snow in the Cave" and "Map of Xishan Plain", all of which imitated the ancients. Although Dong Qichang didn't leave any books and monographs, his experiences and opinions in practice and research can be seen in a large number of inscriptions. Dong Qichang has a famous saying: "Jin people's books take rhyme, Tang people's books take method, and Song people's books take meaning." This is the first time in history that calligraphy theorists defined the aesthetic orientation of calligraphy in Jin and Tang Dynasties with three concepts: rhyme, method and meaning. These viewpoints are very helpful for people to understand and learn classical calligraphy.