Systems and methods for generating an adaptive playlist on a computing device onboard a vehicle are provided. The system may include an onboard vehicle computing device configured to execute a media player program. The media player program may include 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. The playlist manager module may include a playlist generation engine configured to generate an adaptive playlist including user playlist media items, and a contextual media selection engine configured to select contextual media items based on the dynamic contextual data and interleave the selected contextual media items into the adaptive playlist.