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The popular hit song, “Hit the road, Jack,” is as much a part of American culture and slang as Jack Kerouac’s bestselling account of his life on the American highway, On the Road. For better or worse, North Americans have always been on the road, pushing westward towards California, Oregon and British Columbia, moving around the country in pursuit of the American Dream, or just driving along Route 66 to escape the mundane suburban life. This restlessness and the ease with which large segments of the population move and resettle characterizes many aspects of US and Canadian life, turning the road into one of the most powerful symbols in North American literature and culture. Through the analysis of various media forms, which may include film, fiction, music, material culture and architecture, this course will consider the road in America as reality and icon, extending it to the recent emergence of the Internet and the “information highway.”