H. T. Webster, aka Harold Tucker Webster, was a prolific cartoonist who drew more than 16,000 single-panel cartoons in his career from the 1920s into the 1950s. He disliked his given name so his readers knew him as H. T. Webster or simply as Webster, which is how he signed his cartoons. Webster grew up in Tomahawk, Wisconsin. He sold his first cartoon for $5 when he was 12 to the magazine Recreation and studied drawing from a correspondence course when he was 15. Two years later, he left Tomahawk and high school, moving to Chicago to attend the Frank Holmes School of Illustration. A few weeks after his arrival, the school closed, thus ending Webster’s formal education.
Webster’s most famous syndicated cartoon series is The Timid Soul featuring Caspar Milquetoast, a wimpy character whose name is derived from milk toast. Webster described Caspar Milquetoast as "the man who speaks softly and gets hit with a big stick". The modern dictionary definition of milquetoast (meaning a very shy or retiring person) comes from Webster's cartoons.