As real-time 2-way networks are becoming common place, the industry has begun to shift its focus to the advanced services that can now be offered in our digital network environments. Applications such as Internet-on- TV and Video on Demand are in initial deployment and trial phases worldwide. Video on Demand, however, tends to be associated mostly with “Movies on Demand” – allowing subscribers to watch a movie whenever they wish and having VCR-like capabilities. There are, however, many different applications of Video on Demand, each bringing unique revenue opportunities and technical challenges. As we begin to move past the initial deployments and become comfortable with basic Video on Demand services, such as Movies on Demand, we can begin to explore other applications that utilize on demand video streaming, and thus leveraging our investments. This paper will review various Video on Demand applications, their technical infrastructure, business model overviews, and technical challenges ahead.