H. T. Webster was born in 1885 in Parkersburg, West Virginia. He started his comics drawing career when he was twenty years old by getting published in an outdoor magazine called Recreation. Then he got a job as a sports cartoonist at the Denver Post. Not much later, Webster did some freelance work for the Chicago News, followed by jobs at the Chicago Inter-Ocean and the Cincinnati Post, where he got to draw political cartoons.
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In 1912, Webster landed a prestigious job at the New York Tribune, where he created two of his most famous comics, 'Poker Portraits' and 'Life's Darkest Moment'. After a short stint at the New York World, where he created 'The Man in the Brown Derby', he made his comics comeback at the Tribune, creating his best-known comic, 'Timid Soul'. Harold Webster kept working on the Timid Soul Sunday comic until his death in 1953. Webster's longtime assistant and ghost artist Herb Roth continued his features for another year, when he also passed away.