The invention has many different applications and implementations. One or more embodiments of the invention, however, are directed to a software program and/or computer hardware configured to enable users to select one or more master clips having predefined gaps, obtain insert data (e.g., an insert clip), seamlessly merge the insert data into the selected master clip to generate a media clip, and distribute the media clip having the insert data to one or more receiving users for playback. The method of distribution can vary, but in one or more embodiments of the invention the system is configured to obtain user information from a server, assemble personalized media clips (e.g., file(s)) based on that user information, and distribute the personalized media file to one or more users associated with that user information. Embodiments of the invention may utilize scaleable architectures to process any number of users and/or recipients.