H. L. Mencken was born in Baltimore, Maryland, on September 12, 1880, the eldest of Anna Margaret and August Mencken's four children. August co-owned a cigar factory with his brother, and their success enabled him to buy a three-story brick home for his family. Mencken spent most of his life there, living elsewhere only during the five years he was married to Sara Powell Haardt (1930-1935). August paid special attention to his sons, fostering their talents and praising their accomplishments. When he was eight, Mencken developed a keen interest in reading and writing, which led to exceptional study habits. At the age of almost sixteen, he graduated at the top of his class at Polytechnic Institute.

Reluctantly, Mencken joined his father and uncle in their business, but when August died suddenly in 1899, the boy pursued his interest in journalism. He began working for the Baltimore Morning Herald, becoming...