A system for generating an optimized video including in-stream events for video content and advertising content selected at the time of playback. The system includes a manifest generating module configured to retrieve video content from a content repository for listing in a content manifest in response to a received request from a mobile device, the content manifest including at least one advertisement insertion point. The system further includes an advertising event correlation module configured to retrieve one or more advertisements based on a correlation between advertisement properties and playback properties and an advertisement serving module configured to provide the retrieved one or more advertisement for insertion into the at least one advertisement event insertion point.