There is provided an information processing apparatus including a music storage portion to store music data, a music playback portion to play back music data, a metadata acquisition portion to acquire metadata describing information about the music data being played back in the music playback portion, a metadata transmission portion to transmit the metadata acquired in the metadata acquisition portion to the distribution server, a music reception portion to receive music data selected in the distribution server based on the information contained in the metadata and distributed from the distribution server, a music acquisition portion to acquire the music data from the music storage portion based on the information contained in the metadata, and a control portion to control the music playback portion to play back the music data distributed from the distribution server and the music data acquired from the music storage portion by the music acquisition portion.