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.

However, the Holmes School closed only a few weeks after Webster's arrival, bringing an end to his formal art training.

[1] In 1952, Webster suffered a heart attack while on a train that was just arriving in Stamford, Connecticut; he died shortly thereafter.

In 1924, he moved to the New York World and soon after added The Timid Soul featuring Caspar Milquetoast, a wimpy character whose name is derived from milk toast.

Youth's glories (The Thrill That Comes Once in a Lifetime) and the downside (Life's Darkest Moment) appeared on Saturdays and Tuesdays.

When Roth died the following year, the series came to an end with the last new drawing appearing in the New York Herald Tribune on April 4, 1953.

A cartoon published in a 1923 issue of New York World appears to depict a hypothetical machine which some suggest to be a prediction of AI-powered art generators by the year 2023.