[Object] It is desired that the user intuitively perceives the relationship between the plurality of pieces of content and the piece of content that is currently being played back.[Solution] Provided is an information processing system including an output control unit configured to control a display output unit in a manner that a display object indicating a sequential passage of time is displayed. The display object indicates a playback position of content, the display object including a plurality of areas corresponding to a plurality of pieces of the content.