Song shuffling system plays a series of songs selected from a shuffled plurality of predefined audio content sources. An exemplary embodiment concurrently receives, during a shuffle operation, a stream of audio content from each of the predefined audio content sources, wherein each of the streams of audio content comprises a plurality of serially received songs. Each song is stored by the media device as the song is received. A first predefined audio content source is selected from the predefined audio content sources. Then, a first song is selected having a beginning portion that is stored in the memory medium and that was provided by the selected first predefined audio content source. A second predefined audio content source is selected from the predefined audio content sources that is to provide a second song that is to be presented to the user upon conclusion of the presentation of the first song.