Based on the cult classic book of the same name, written by Josh Alan Friedman, Tales of Times Square combines 16 mm footage and grainy Super 8, as well as original 35mm photography by Porn Star Annie Sprinkle, to paint a vivid picture of Times Square's seedy past, the sex industries that thrived there, and those threatened with extinction by a movement to 'sanitize the square.' The film investigates the past, present and future of the infamous neighborhood, at the height of its raunchy reputation.

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