The objective of this chapter is to develop a method for generating and analyzing creative work by using computers. In this chapter, novels, comics, and animations are considered representative creative work because the main method for representing creative work is the use of natural language and pictures. These works focus on interesting issues, which can be explained by computational approaches to narratology. In this chapter, the authors discuss the following three topics. First, a method of semi-automatic story generation by agent-based simulation is presented. Second, methods of generating and analyzing comics on the basis of the features of pictures and stories used are described. Third, the authors introduce a method of estimating the difficulties of translating a storyboard into original pictures in the process of creating animations.