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Webster’s Unalloyed

May 2024
3min read

H. T. Webster’s cartoons offer a warm, canny, and utterly accurate view of an era of everyday middle-class life

H. T. Webster was not a great artist. Once he had established a style, it hardly changed in more than forty years of drawing. Indeed, in mid-career he lost the use of his right hand due to acute arthritis, but in a few months he was drawing with his left, and his later work is quite indistinguishable from his earlier. Moreover, Webster’s style was highly reminiscent of Clare Briggs, the cartoonist a generation older who invented the comic strip.

But if only an adequate artist, Webster was a very great cartoonist, for he had the gift of finding the universal in the particular. Day after day he would draw a few spare lines, add a swash or two of black, a dozen words or so, and millions of middle-class newspaper readers would recognize themselves, their neighbors, their children in the act of being human, and laugh.

Webster captured with apparent ease (apparent ease, of course, is almost always the result of very hard work) the myriad minor moments of his life and times. Because he was such an acute observer, his cartoons are still a window into his world, that of middle-class America in the period framed by the two world wars.

Looking at his cartoons, a person might conclude that Webster was a gentle, happily married man who was fond of golf, fishing, poker, bridge, and dogs. And that is precisely what he was: Webster almost always portrayed the world from his own perspective. He even drew many cartoons about the travails of being a cartoonist.


Since he had no children himself, his many drawings involving them usually harked back to his own turn-of-the-century childhood. One shows a small boy proudly presenting a tiny fish he has just caught to his parents, who carry on as though he had landed leviathan. Although the cartoon was drawn in 1948, the mother is wearing a long skirt just as his own mother had done fifty years earlier.

Webster was born in 1885 in Parkersburg, West Virginia, and his parents named him Harold Tucker. He loathed his first name and always signed himself with his initials. To his friends he was known as Webby. When Webster was still a boy, his father, a druggist, moved the family to a small town in Wisconsin with the improbable name of Tomahawk. While Webster would live most of his adult life in the great world centered on New York City, there was always much of small-town America in his work.

Webster’s art education was, well, sketchy. He got the lowest marks in his school drawing class (mainly because he drew what he wanted to draw and not what—still less how—he was told to). Leaving Tomahawk at the age of seventeen, he enrolled in Frank Holmes’s School of Illustration in Chicago, only to have it close a couple of weeks later. That concluded his formal art training.

He vowed to make his little pictures so big a million people could see them at once—and he Succeeded.

But the young H. T. Webster sketched endlessly and had no doubt what he wanted to do in life. A boy-hood friend taunted him that he was going to spend his life drawing little pictures instead of doing something important. Webster retorted that he was going to draw big pictures, so big a million people could see them at once. Webster recalled the incident with satisfaction many years later when his cartoons were appearing in newspapers that had a combined circulation of nearly twelve million.

His first job was with the Denver Republican , but he shifted over to the rival Post when it offered him $15.00 a week as a sports cartoonist, a very good salary at that time for someone still in his teens. (Webster later remarked that “if they had known it, they could have got me for $1.50.”)

Soon back in Chicago, he began to do political cartoons. Before long these were appearing on the front page of the Chicago Inter-Ocean and obviously reaching their targets. One wounded political Pooh-Bah, doubtless to Webster’s delight, actually introduced a bill in the state legislature forbidding uncomplimentary cartoons.

Webster moved from newspaper to newspaper as his career expanded, and he took a year off to travel around the world before settling in New York in 1913. In 1919 he began his association with the New York Tribune (soon merged with the Herald ). Except for a seven-year stint with the New York World , he was with the Trib the rest of his life, his daily cartoon appearing on the front page of the second section. For many readers it was the first thing they looked at after the headlines.


Webster specialized in the single frame cartoon, each a part of one of a number of series he developed over the years. These series included “The Thrill That Comes Once in a Lifetime,” “Life’s Darkest Moment,” “Poker Portraits,” “Bridge,” “How to Torture Your Wife” (and “How to Torture Your Husband,”) “Fishing,” and, by far the most famous, “The Timid Soul.”

The Timid Soul was a middle-aged American whom Webster named Caspar Milquetoast, a word that is now in every dictionary. Mr. Milquetoast was a kindhearted, decent man who hated to offend anyone and consequently was a pushover. His overactive conscience caused him to obey every law scrupulously, even to the point of hurrying past No Loitering signs.

The appeal of this character to Webster’s audience is easy to understand. Anyone who has ever allowed himself to be buffaloed into doing something he didn’t want to do or automatically feels guilty while clearing customs can identify with Caspar Milquetoast.

For the last two decades of his life, Webster pursued the even tenor of his way, turning out cartoons for the Herald Tribune , wintering in Florida, summering in Connecticut, playing bridge, and fishing with his many friends. Then, on September 22, 1952, he collapsed and died while returning to his home in Connecticut after a weekend fishing trip with his friends. His cartoons continued to run in the Tribune until the backlog was exhausted, the last one appearing on April 4, 1953. That day, wrote the playwright Robert E. Sherwood, was for millions of Americans one of life’s darkest moments.


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