The present invention relates to an information processing apparatus for controlling content reproduction on a basis of a first weight set to a playlist of contents and indicating a priority of the playlist and a second weight set to each of contents registered in playlists and indicating a priority of the content. The information processing apparatus includes a weight setting unit for, when a plurality of playlists are selected, updating a first weight set to each of the plurality of selected playlists and updating a second weight set to each of contents registered in the plurality of selected playlists according to one of a number of playlists in which each of the contents is registered and a specified reproduction method, and a reproduction controlling unit for controlling random content reproduction on a basis of the first weight and the second weight set by the weight setting unit.