1. A system for generating an adaptive playlist on a computing device onboard a vehicle, the system comprising: an onboard vehicle computing device configured to execute a media player program, the media player program including: a media storage module configured to store a plurality of media items; a user preference module having user media preferences; a contextual data module configured to receive dynamic contextual data from an onboard vehicle data source; and a playlist manager module including: a playlist generation engine configured to generate an adaptive playlist including a plurality of user playlist media items selected from the plurality of media items based on the user preferences; and a contextual media selection engine configured to select one or more of contextual media items from the plurality of media items, based on the dynamic contextual data received from the onboard vehicle data source, and to interleave the selected one or more contextual media items into the adaptive playlist.