A method and a system may be provided to sample media content similar to media content enjoyed by a user. Feature vectors, which describe a number of characteristics, with respect to media content enjoyed by the user, may be employed to find similar media content from a media library, or a media service. The similar media content may be played, interleaved with requested media content. Relevance feedback, with respect to played media content, may be transparently or explicitly provided. The feature vectors may be updated based on the provided relevance feedback. Additional similar media content may be found from the media library, or the media service, based on the updated feature vectors, and may be played. An interface may be provided such that the user may purchase sampled, media content via a media device for playing the content.