A system and method for providing content offering recommendations to users based on the users' preferences. Content offerings may be assigned to a primary metagenre and one or more sub-genres, as well as a secondary metagenre (and additional sub-genres if desired). The offerings may also be identified by their source, and this information can be used with the primary/secondary metagenre/sub-genre data to prepare a listing of recommended files. The listing may be generated by first generating three match listings: 1) a strong genre match listing identifying those offerings that match two user preferred metagenres; 2) a genre/style match listing identifying those offerings whose primary metagenre and corresponding sub-genre are preferred by the user; and 3) a weak genre match listing identifying those offerings whose primary metagenre matches a user preference, but whose secondary metagenre does not. These listings may be combined, redundancies may be removed, and a subset may be presented to the user as a recommendation list.