Born around the same time as the American comic strip, in 1891, Crosby grew up in a day when newspaper comics were titillating the emerging mass audience for popular entertainment. Unruly, manic, crude, and hostile to propriety, the era’s cartoons captured American popular culture being born, and, nickel by nickel into the millions, they funded the news empires of both Joseph Pulitzer and William Randolph Hearst. When Crosby was a child in New York, the most popular comic strips in America—“The Yellow Kid,” “Happy Hooligan,” “The Katzenjammer Kids,” “Little Jimmy”—centered on the lives of kids growing up in the over-packed, chaotic, scary urban centers of the Northeast. (Few of the strips’ locations were explicitly named, although they all looked like New York City; in fact, most of the comics seemed to take place on a single block of tenements in the Lower East Side.) In the vernacular idiom of cartoon burlesque, the Sunday funnies dealt with the young problems of a new America.

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.

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