A system and method are operable within a computer network environment for compiling a singular video file from user-generated video file fragments for playback in tandem with a context-providing audio file. The system includes at least one client operable to generate at least one video file fragment in tandem with audio file content simultaneously consumable via each client. Each video file fragment is generated at or between a select start time and at a select end time during playback of a select audio file content segment, the parent audio file of which segment has a universally unique identifier. A remote service system compiles the video file fragments into a video file fragment compilation for playback progression in tandem with playback of the audio file content based on the select start and end time of the video file fragments as associated with select audio file content segments of the audio file.