Person who drifts from town to town

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Possible Answers:

Hobo.

Last seen on: Daily Celebrity Crossword – 5/23/19 Top 40 Thursday

Random information on the term “Hobo”:

Jack Black (1871–1932) was a hobo and professional burglar. Born in 1871 near Vancouver, British Columbia, Canada,[citation needed] he was raised from infancy in the U.S. state of Missouri. He wrote You Can’t Win (Macmillan, 1926), a memoir or sketched autobiography describing his days on the road and life as an outlaw. Black’s book was written as an anti-crime book urging criminals to go straight, but it is also his statement of belief in the futility of prisons and the criminal justice system, hence the title of the book. Jack Black was writing from experience, having spent thirty years (fifteen of which were spent in various prisons) as a traveling criminal and offers tales of being a cross-country stick-up man, home burglar, petty thief, and opium fiend. He gained fame through association with William S. Burroughs, and his writings had a profound effect on the writings and lives of all the Beat Generation.[citation needed]

Jack Black is an essentially anonymous figure; even his actual name is uncertain,[according to whom?] Some 1904 news articles name him as Jack Black, alias Tom Callahan, while a 1912 newspaper article names him Thomas Callaghan, alias Jack Black, and another gives his alias as Harry Klein. One of his nicknames among criminals was Blacky.[citation needed]

Hobo on Wikipedia