Computer-based methods and systems for dynamically inserting advertising content into a radio broadcast are provided. Example embodiments provide a Streaming Content System that comprises one or more media servers, an ad content repository, a broadcast throughput channel, an enhanced media encoder interface, and an ad server interface. These components cooperated to request ads that are targeted according to passed personalization data. The ads are inserted dynamically into a stream of audio or video content upon detection of an ad event. To control playback delays, the ads are preferably buffered ahead of their need.