Provided is an information processing apparatus that can display a planar video in a manner suitable for circumstances of use when a planar video is displayed on a video display apparatus used by being worn on the head by a user. The information processing apparatus is connected to a video display apparatus used by being worn on the head by a user and switches between a first display mode in which a planar video is displayed in the front direction of the user irrespective of the change in position and/or orientation of the video display apparatus and a second display mode in which a planar video is displayed in a manner that changes with the change in position and/or orientation of the video display apparatus based on a given condition.