Crosby, like a great many cartoonists then and now, started precociously. At sixteen, he found work in the art department of The Delineator, a women’s magazine—or a “Journal of Fashion, Culture, and Fine Arts”—edited by Theodore Dreiser. He was versatile and, in the early years of his career, malleable. By seventeen, he was working as a political cartoonist, at first for the New York Evening Call, a Socialist broadsheet for which he once did an effectively grim cartoon about the Triangle Shirtwaist Factory disaster (reprinted in Robinson’s book). He showed interest in combining ideology and humor, an inclination that grew with the years in ever-stranger ways. Crosby worked up samples of two politically skewed humor cartoons, “Biff” and “The Extreme Brothers—Laff and Sy,” and the Call published them until readers complained about their frivolousness. Crosby, describing his disappointment in one of several books he published years later, said, “Communists absolutely have no sense of humor, and they positively dread ridicule.”

He bounced around New York publications, ascending with each bounce, till he landed, at age nineteen, at Pulitzer’s New York World, where he worked as a beat artist—a reporter who filed narrative drawings of news events, something of a precursor to today’s visual journalists. Assigned to the Metropolitan section of the Sunday edition, Crosby covered New York politics and crime for a couple of years, then bounced some more among newspapers and magazines (with a stint in the Army during the First World War) until he ended up at Life magazine, producing wry cartoons of social commentary as well as more conventional domestic humor. It was at Life that Crosby developed Skippy.

A boy of five or six who sometimes looked younger and almost always acted older, Skippy was an unprecedented comic-book kid—neither a hooligan nor very happy most of the time. He is no urchin; Crosby dressed him like a little fop in a high-collared shirt, a polka-dot bow tie, and a waistcoat that dangled nearly to his scrunched-up socks. Skippy has empty ovals for eyes and, in most of Crosby’s drawings, no mouth. His face is almost expressionless, like Buster Keaton’s, and, as with Keaton, the surface blankness leads one to imagine Skippy as endlessly complex inside.

He is a solitary character, often depicted sitting on the curb or leaning on a fence by himself; and, even when he is doing something with his friends in the strip’s small group of recurring characters, he is always alone in his point of view, the only one to grasp or to challenge the situation at hand. The backgrounds in the strip are minimal—sometimes just plain white space without so much as a suggestion of setting. Skippy occupies a space not abstracted, in the manner of the desert-mirage dreamscapes of Herriman’s “Krazy Kat,” but subtracted. He lives nowhere in particular but in his head, and his lonesomeness is the deep source of Skippy’s veracity. Childhood is a lonesome time, as former children often forget. The lonesomest kid in the comics, Skippy was also the realest one until Charlie Brown.

Indeed, Skippy was the first realistic, believable child in the comic strips, as Robinson points out early in his book. “The brilliance of Skippy,” Robinson argues, “was that here was a fantasy with a realistic base, the first kid cartoon with a definable and complex personality grounded in daily life.” Skippy is invariably occupied, to the low degree that he is occupied by anything, by the everyday matters in a young person’s life—working a gumball machine, bringing home his report card, avoiding a bath.

As I mentioned, I had seen the 1931 live-action Skippy movie in a film-history class session on child actors, and I had found it sweet and gently humorous; Jackie Cooper, at age nine, was nominated for an Oscar for Best Actor for his performance in the title role. Until I read Jerry Robinson’s book, though, I had not realized that the film, just like all the movies made from comic books in recent years, was only one element in a multi-platform franchise that predated those buzzwords by half a century. Once Crosby moved “Skippy” from Life magazine into newspaper syndication in 1925, it reached millions of readers in hundreds of newspapers around the United States. There was a Skippy radio show; novels about Skippy written by Crosby; a popular song about Skippy (“You can always see him in the daily papers/you’ll love his capers”); Skippy dolls; Skippy trading cards; Skippy jigsaw puzzles; a Skippy wagon; a Skippy sled; and Skippy eyeglass frames (complete with a sticker certifying, “This case contains a pair of genuine ‘Skippy’ glasses,” despite the fact that Skippy didn’t wear glasses).

David Hajdu is a professor of arts and culture journalism at Columbia's Graduate School of Journalism.