Provided is an information processing device including: a data processing unit that performs a content playback process; and a communication unit that communicates with a server, wherein the content is content that has a segment region configured with a plurality of pieces of variation data which can be respectively decrypted by different keys, and for which a plurality of playback paths can be configured according to variation data which is selected as a playback object, wherein each piece of variation data is data for which a variation data identifier can be analyzed from decrypted data, and wherein the data processing unit receives playback path information which is allowed to be played from the server through the communication unit, and selects variation data from the segment region so as to perform content playback, according to the playback path information received from the server.