A novel and useful system and method of automatic resource connection, selection and rating for providing a radio like listening experience to a user. The mechanism is operative to automatically establish a connection from a mobile communications device having media player capability to a music file collection. Playlists maintained on the device are periodically updated with new playlists downloaded to the device. The device generates playlists so as to eventually cycle though the entire contents of a music file collection. Users are given the ability to rate songs by title, artist, album, etc. These ratings are used to calculate scores for each song which are used to bias a random selection process for determining the next song to play. This provides a user with a radio like listening experience.