A play list of songs or other media items is automatically generated (380) based on external factors (314, 324, 334) such as weather conditions, stock market conditions, sales of songs, or calendar data, e.g., day of week, holidays or user designated dates such as birthdays, anniversaries and the like. External data (310, 320, 330) relating to the external factors can be received (115) from a radio broadcast, Internet link, or link to a vehicle computer, for instance. The external data is mapped (360) to media items to obtain matching media items (370) for the play list. The mapping may also account for user preferences (145). The user may select (305) the external factor, which represents the mood and/or current preferences of the user in a much better way than the conventional criteria such as genre, artist or album alone.