This paper proposes a dynamic shadow generation system that combines the shadow of an object with the artificial shadows of virtual characters. In our proposed system, infrared light is used to capture an object’s shadow in order to discriminate between a shadow generated by an object and a virtual shadow generated by the system. Our proposed system determines areas in which shadows do not appear and then the shadows of virtual characters are added to these areas. This paper presents the basic idea of the system, the shadow generation algorithm that it uses, and an empirical study on the sharpness of a generated shadow, along with the distance between an object and a screen used in this system.