Because of the humor and human interest in his cartoons, he was sometimes compared to Mark Twain, and his art style was quite similar to the work of Clare Briggs. During his lifetime, Webster drew more than 16,000 single-panel cartoons.

Born in Parkersburg, West Virginia in 1885, Webster grew up in the small city (pop. 3,365) of Tomahawk, Wisconsin where his father was a druggist.[2] He began drawing at age seven. When he was 12, he switched from cigarettes to cigars, and that same year he sold his first cartoon for $5 to the magazine Recreation.