A system for sharing playlists and playlist essence with different users. A user desiring to share his or her playlist generates the playlist and a playlist characterization. The playlist characterization is based on acoustic analysis data of one or more songs in the playlist. The playlist and playlist characterization is then transmitted to another end user device. The end user device receiving the shared playlist searches the user's music collection for the songs in the playlist. If a gap is detected in the playlist because the receiving user does not own a particular song, the receiving end user devices automatically selects another song that is owned by the user to fill-in the gap. The song is selected based on the playlist characterization with the aim of preserving the essence of the shared playlist.