In 1912, Webster drew a daily panel for the New-York Tribune, under a variety of titles—Our Boyhood Ambitions, Life's Darkest Moment, The Unseen Audience.

In 1924, Webster moved to the New York World and soon after added The Timid Soul featuring the wimpy Caspar Milquetoast.

The accompanying article said, "millions of Americans know Caspar Milquetoast as well as they know Tom Sawyer and Andrew Jackson, better than they know George F. Babbitt, and any amount better than they know such world figures as Mr. Micawber and Don Quixote.

When the term is used to describe a person, it typically indicates someone of an unusually meek, bland, soft, or submissive nature, who is easily overlooked, written off, and who may also appear overly sensitive, timid, indecisive or cowardly.

[7] One journalist has suggested that Casper the Friendly Ghost, a cartoon character originating in the late 1930s, was a spoof named partially after Webster's Milquetoast, although there has been no official confirmation of this relationship.