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Cobb is remembered best for his humorous stories of Kentucky and is part of the American literary regionalism school. These stories were collected first in the book Old Judge Priest (1915), whose title character was based on a prominent West Kentucky judge named William Pitman Bishop. Writer Joel Harris wrote of these tales, "Cobb created a South peopled with honorable citizens, charming eccentrics, and loyal, subservient blacks, but at their best the Judge Priest stories are dramatic and compelling, using a wealth of precisely rendered detail to evoke a powerful mood."Among his other books are the humorous Speaking of Operations (1916), and anti-prohibition ode to bourbon, Red Likker (1929).