Disclosed herein are an information processing apparatus and method, a program, and a recording medium, in which a content is recommended to each user on the basis of even the metadata that is assigned with no classification. A metadata analysis block resolves metadata acquired by a metadata acquisition block into components. A dictionary data generation block generates dictionary data in which genre is correlated with keyword and each component. An associated-information database generation block references the dictionary data to assign genre to the metadata which are assigned with no genre, thereby generating an associated-information database of content. An associated-information search block references the dictionary data to identify a genre from a keyword of interest data to search for associated information, thereby recommending content to the user. The present invention is applicable to personal computers or HDD recorders.