Information distribution systems and information distribution methods are provided. In an information distribution system, header files of contents in accordance with a preference of a user of a data terminal are automatically selected, in advance, from a content distribution apparatus and are transmitted to the data terminal, so that probabilities that the header files of the contents have been already stored are very high when the user downloads the content of the body data. If the number of header files to be stored is more than a predetermined number, the most of the header files with respect to the contents of the body data to be downloaded will be in the data terminal. Therefore, on performing a downloading operation, the header files can be played immediately, then subsequently, the downloaded content of the body data are played, whereby the user can appreciate the content which the user desires to view and listen to without waiting time.