Systems and methods for personalizing video playback are disclosed. In embodiments, a computer-implemented method, comprises: initiating, by a computing device, a video playing session of a video; recording, by the computing device, user initiated playback actions during the video playing session as playback event data; determining, by the computing device, context data based on content of the video, and saving the context data; determining, by the computing device, insights regarding the user playback event data utilizing the context data; and generating, by the computing device, one or more recommendations based on the insights.