The present invention provides an information processing apparatus which can direct a user to a playlist different from a playlist being reproduced. There is provided the information processing apparatus including a content storage unit storing a plurality of contents therein, a playlist storage unit storing a plurality of playlists which is related to at least some of the plurality of contents, a reproducing unit sequentially reproducing a plurality of contents belonging to a first playlist in a plurality of playlists, a candidate content extracting unit extracting one or more candidate contents relating to a content being reproduced by the reproducing unit from the content storage unit, a playlist extracting unit extracting a second playlist to which the extracted candidate contents belong from the playlist storage unit, and a playlist switching unit switching a playlist to be reproduced by the reproducing unit from the first playlist into the second playlist.