Conversation in the cloud is a live multimedia composition by one human musician and one AI musician. The conversation between the two musicians starts at the intersection of reality and virtuality via music. Then, both musicians will drive their limits through improvisation founded on each other’s music during the live performance. Finally, the two worlds slowly merge as the conversation deepens. The AI musician is a comprehensive system that involves multiple machine learning techniques to enhance its machine musicianship, such as deep neural network and human body pose estimation. Thus, the combination of live multimedia and performances from the two musicians unveils a multidimensional music conversation.