A portable digital media player and method for providing convenient music recommendation are presented. A collection of music is maintained and includes a multiplicity of music stored in digital media form. A music recommendation is automatically generated in response to a recommender input. An identifier for a recipient is provided. Music to be recommended is identified from one of the music collection and a sample of music in an ambient environment. Information to the music recommendation to describe the music to be recommended, to identify the recommender, to capture a context of the recommendation, and to specify a rating for the music to be recommended is ascertained and added to the music recommendation. The music recommendation is sent for electronic receipt by the recipient.