This study investigates the portrait paintings of the Chosun period and the Death Records of the Chosun-dynasty Sillok in an effort to find new methods to apply to character design. The basis of this study were 42 figures from a group of portrait paintings from the late Goryeo period to the Chosun dynasty of the 25th King, Chul-Jong. First, Chinese letters illustrating the personalities in the Death Records were classified into five groups based on the Big Five theory, which divides personalities into the Big Five Personality Traits of extraversion, agreeableness, conscientiousness, neuroticism, and openness. Secondly, a representative facial image was created through a morphing technique after extracting the portraits using a method that relied on the high frequency of the appearance of specific Chinese letters related to each personality type.