The Fresh Annotator is a creative engagement application designed to help students forge a personal connection with hip-hop educational content through play. The initial middle school history content is delivered in the form of multimedia lyrics which include keywords that students can annotate with drawings, their own audio, text, or video. Students can play back and live-jam to their annotations. Teachers can access online and use without having to create a login account or downloading and installing any software. The tool is designed so that it can be used by students individually or collaboratively as a group. Individual sessions are saved as unique URLs.