A system for generating a play-list includes a media player and a media file server. The media player automatically generates weight values of each media file therein. The media file server stores a plurality of category tables, each category table storing a desired sub-category and corresponding sub-category weight values; initializes the category tables in response to an operational input for generating a play-list; obtains a predetermined amount of media files from the media player; reads the desired sub-categories and the weight values of the obtained media files; increments a corresponding sub-category weight value in the corresponding initialized category tables by the read weight values; calculates final weight values of each media file according to the category tables; and generates the play-list of the media files according to the final weight values thereof. The present invention also provides a corresponding method that makes the play-list more suitable for the user's favors.