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The song is about the Great Depression of the 1930s, when jobs were very scarce and workingmen caught rides on freight trains to go where there might be work, often in distant parts of the country, since they had no money for travel. Railroad police looked for them, but some railroad workers looked the other way. Water tanks were placed at intervals along rail lines to replenish the water for steam locomotives. Since trains stopped there, they were a place where the hobos (railroad bums) waited for them. Some of the men came to enjoy the freedom of riding the rails, and it became a way of life, about which many songs have been written.
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