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Terry Southern's life and career unfold through a vibrant exploration of American culture from the conservative 1950s to the dynamic 1990s. The narrative highlights his influential role in shaping New Journalism and independent cinema, notably through his work on Easy Rider. It features a range of Southern's writings, including his iconic pieces in Esquire and personal anecdotes involving cultural icons like Abbie Hoffman and Stanley Kubrick. This journey captures the essence of an audacious figure who navigated the intersections of art, politics, and counterculture.