This episode examines the Outlaw Country genre of the 1970s with respect to freedom: both in the sense of the artistic freedom that figures like Kris Kristofferson, Willie Nelson, and Waylon Jennings sought within the Nashville system and in the sense of freedom as a topic within the songs themselves. The second segment comes to grips with Kant's ideas about freedom and all the potential ambiguities it presents. Then I turn to the issue of US rugged individualism and its impact on Outlaw Country.