|Characters were created as pictorical representation of speech and various sounds of nature. Character painting has attempted a deconstructive approach in the process of creating pictures with characters, sounds with characters and vise versa. The purpose of this study is to analyze the methods, characteristics and approaches of deconstructive character paintings, suggesting the spirits and directions of this era to encourage higher-level of creativity and creation of more advanced, unconventional works in all fields of visual arts. This study deals with the history of letters, the relatedness of character painting and deconstructive approach, analysis of world-class character painting artists`` works, the theories of character paintings created with repeated letters, words and numbers, its deviant characteristics, and clarified its problems and prospects. Also, this study demonstrates and investigates the fact that Jacques Derrida``s Deconstructionism has to do with nature, scatteredness, spaces and redundancy. The author has discovered that creation of character painting has problems that go against the basic spirits of deconstruction, such as excessive uses of English alphabets, Chinese characters and flat surface expressions, calling for expansion of Korean character painting creation with letters proved to be the most scientistic in the world as a solution. In order to do so, the author has suggested internationalization of Korean character paintings, establishment of its identity and continuous experiments of revolutionary methods using various mediums such as flat and three-dimensional surfaces, device installation, LED and 3D image methods.