A method of conducting a disc jockey (DJ) commentary analysis for indexing and search is provided. More specifically, a method is provided for automatically generating metadata related to commentary of media segments to enable tagging, storing and context relevant searching. Speech-to-text conversion technology and audio/video analysis are used to generate content and metadata. Subject matter is then identified and filtered to a predetermined set of subjects. Metadata tags and context profiles for the media segments are generated to index the media segments. Moreover, context information of the user is used to generate a context profile of the user in a format similar to that of the media segment. Indexed media segments are searched to match with the user context profile and a relevant media segment is presented to the user.