In this chapter, we present an intelligent media oriented e-learning system. In this system, we have developed a LMS (Learning Management System), some learning control systems and some learning media, with a flexible framework. It is intended to provide a collaborative workplace to encourage interactions among lecturer/learners. Moreover, we propose an innovative educational method of a cooperative link between a university and an industry for higher education. We analyze these results and the problems we encountered, as well as offer constructive solutions. Furthermore, we have developed some intelligent media such as an analyzer/summarizer by the statistical natural language processing for data log of discussion process to encourage/aware discussion/negotiation between learners and an automatic reporting processor.