Jungchull(정철) was a very famous poet of Kasa(가사), Sijo(시조) and Hansi(한시) during the middle period of the Chosun kingdom. He has been studied by modern scholars mainly as a poet of Kasa(가사). These days, however, his Sijos are being studied as an important literary achievement. The purpose of this study is to analyze the pursuit of reality and elegance expressed in Jungchull's Sijo in order to understand his Sijos more deeply. In the process of this discussion, I will take a look at some of his Kasa(가사), Hansi(한시) and biography also, and I will compare his Sijo(시조) with that of his teacher's, friend's and senior's. Jungchull considered it important to become an official in the royal court because he was a Confucian scholar who believed in jugi-theory (주기론), in which all realistic phenomena is evaluated(Confucianism is very realistic in essence), and he had a happy life in the royal household until he was ten years old. I found that characteristics of his "realistic pursuit" are represented in his Sijo by two situations: the one is when he is apart from the King, and the other when he is together with the King. In all situations, though, he pursued an official position in the royal court. When he was apart from the king, his absolute resolution to follow the King was expressed in his not being able to sleep. In his sijo, he asks the wild duck to inform him of the King's welfare. He tries to flap his wings, to be the water or the moon in order to reach the royal household where the King was living. When he recognizes it's impossible, he expresses his perfect loyalty to the King in his Sijo by using literary paradox. According to this, he describes himself as not an able scholar, but also not a flattering scholar. In his sijo, he reminisces about working for the King in the royal household, when he had a good relationship with the King. But when he was an official in the province in a good relationship with the King, he expressed his intention of coming back to the royal household in order to be with the King again. From this we can ascertain that his pursuit of reality means to occupy an official position in the royal household, to serve the King and to have political power among of the officials. His elegance, expressed in his sijo, is deeply related to his absolute political pursuit of the King. He describes two kinds of elegance: nature related elegance and drinking alcohol related elegance. Two kinds of nature related elegance were delineated in his sijo, depending upon his political situation. When he had a good relationship with the King, occupying an official position, he delineated his gladness and free-heart in harmonizing with nature. But when he lost his official position. he expressed his purity using nature, and exclusion from nature. These kinds of nature related elegance were different from that of the usual Confucian scholar, for example, contemporaries Lee Hwang Next, two kinds of drinking alcohol related elegance were delineated in his sijo depending upon his political situation. More often he depicted excitement and composure of mind in his sijo by drinking alcohol in good situations than in efforts to overcome his agony in bad situations. The tradition of overcoming one's agony by drinking alcohol in bad situation was discovered by this writer in Jungchull's teacher's, and also his junior's sijo. Lastly in my next research paper future, I will look at the reason why certain various themes are represented in Jungchull's sijo, and what their the relationships are, to understand his literary works as a whole.