13. A method for generating an adaptive playlist for a media player executed on an onboard vehicle computing device of a vehicle, the method comprising: generating an adaptive playlist including a plurality of user playlist media items selected from a plurality of stored media items based on user media preferences for a user; and receiving in real-time, while the vehicle is moving, current contextual data from an onboard vehicle data source, wherein the current contextual data includes calendar information of the user received at the onboard vehicle data source from a user account at a remote data source via a wireless communication link, the calendar information comprising one or more of personal calendar entries of the user, shared calendar entries for a shared calendar to which the user subscribes, and synced calendar entries from a synced calendar maintained on a portable device associated with the user; tracking and storing the current contextual data history over time, and correlating the current contextual data history with the user media preferences; selecting in real-time, while the vehicle is moving, one or more contextual media items from the plurality of media items, based on dynamic contextual data including the calendar information received at the onboard vehicle data source from the remote data source; interleaving in real-time, while the vehicle is moving, the selected one or more contextual media items into the adaptive playlist; removing in real-time, while the vehicle is moving, the selected one or more contextual media items from the adaptive playlist; playing the media items in the adaptive playlist via an output device.
15. The method of claim 13 , wherein the user media preferences include one or more of a track preference, a genre preference, an artist preference, a media preference, or a religious preference, and are based on historical listening patterns of the user.