15 famous people come from Ashland, Ernest Cline the best known
Ernest Cline is the best known, with articles in 28 languages. Second and third on the list are Edmund G. Ross and Tim Richmond. 6 of them were born between 1920 and 1969, more than in any other period. Births since 1970 account for 2 of the names.
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From Wikidata and Wikipedia: people whose birthplace is Ashland and whose English Wikipedia article agrees, ranked by how many Wikipedia languages cover each person. People known mainly for crimes, and adult performers, aren’t listed. “The usual town” = everyone born in the towns gathered so far.
Arthur B. Williams: Frontispiece of 1926's "Arthur B. Williams, Late a Representative." US Government Printing Office., Public domain, Wikimedia Commons