Wouldn't you like to have had a cup of coffee or a good Manhattan with that fellow? There's a challenge to that expression, but it's not agressive. It's as agreeable and amusing as his work. He was. . .

Harold Tucker Webster (September 21, 1885 – September 22, 1952) was an American cartoonist known for The Timid Soul, Bridge, Life's Darkest Momentsand others in his syndicated series which ran from the 1920s into the 1950s. Because he disliked his given name, his readers knew him as H. T. Webster, and his signature was simply Webster. His friends, however, called him Webby. 

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.

He had a schedule:

He alternated his various features throughout the week: Caspar Milquetoast was seen on both Sunday and Monday. Youth's glories (The Thrill That Comes Once in a Lifetime) and the downside (Life's Darkest Moment) appeared on Saturdays and Tuesdays. On Wednesday, The Unseen Audience offered satirical jabs at radio. How to Torture Your Husband (or Wife) was published each Thursday, and the week ended with Bridge on Fridays.

First we'll examine his 1919 panels, followed by work from other decades. Webster was one of the first forgotten characters I discovered waaaay back in high school, and I've always had a soft spot for his work.

NOTE: Caspar Milquetoast has been redone, with 20 more examples added in 2020.