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Jack Black was a burglar, rambler, jailbird and writer whose lone published memoir, You Can’t Win (1926), was an important early influence on William S. Burroughs and, through him, the other Beat writers. With a film adaptation of the book, starring Michael Pitt, expected later this year, now is a good time to rediscover this classic road narrative. Anthony Mostrom tells the story of Jack Black through his own words and those of Burroughs.