No American illustrator captured the quirks and codes of early 20th-century society quite like Charles Dana Gibson, and "Advice to caddies" stands as a testament to his sharp eye for social nuance. Gibson’s witty drawings, often published in magazines such as Life and Collier's, became so influential that his name gave rise to the “Gibson Girl”—an icon of modern womanhood. While the exact date and medium of this particular work remain uncertain, its subject matter and style unmistakably place it within Gibson’s heyday, when golf was emerging as a fashionable pastime among the American elite. In "Advice to caddies," Gibson zeroes in on a moment of mentorship—or perhaps mischief—on the golf course.

A seasoned golfer, depicted with the upright bearing and crisp attire of his class, leans in to dispense wisdom to a pair of young caddies. Their attentive, slightly wary faces suggest the weight of the golfer’s words, while the background, sketched with Gibson’s signature economy, hints at the manicured expanse of a private club. The caddies’ caps and simple clothing mark their station, and the subtle humor lies in the contrast between the earnestness of the advice and the boys’ likely skepticism.

This gentle satire recalls the social observations of George du Maurier, though Gibson’s line is bolder and his tone more distinctly American. As with much of Gibson’s work, "Advice to caddies" was probably first seen by the public in a popular periodical, reaching thousands of readers who recognized themselves—or their aspirations—in its scenes. Original drawings by Gibson are now prized by collectors, though many survive only as prints or magazine clippings. The precise whereabouts of this original are unclear, but similar works reside in collections such as the Library of Congress and the Smithsonian.

"Advice to caddies" reflects Gibson’s lifelong fascination with the rituals and hierarchies of leisure, and remains a lively document of an era when golf, and the social dance around it, was still new terrain for both artist and audience.