A method for use in an automated media scheduling system includes generating a shots representing potential playlists of media items. Each of the shots includes multiple shot positions. A shot-position-dependent score of a current content item being considered for insertion into a particular shot position of a particular shot is generated, and indicates how closely the current content item conforms to a predetermined set of factors associated with the particular shot position of the particular shot. The current content item is inserted into the particular shot position of the particular shot based, at least in part on a comparison of the shot-position-dependent score of the current content item with shot-position-dependent scores of other content items, and the shot positions of each of the shots are populated with eligible content items. One of the shots is selected for scheduling based on aggregate scores of eligible content associated with each individual shot.