The American West has its own mythology, bolstered by characters who’ve taken on their own significance over the course of their representation across film and painting and literature: Natives and cowboys, the horses they ride, the landscapes that backdrop their good-and-evil adventures. Thomas Blackshear knows its traditions well, having dedicated a good portion of his illustrative practice to the Western school of art. “I can say that a lot of my work is centered around storytelling,” he tells Document.

Blackshear was recently commissioned by Stetson—the American heritage brand near-synonymous with the lore of the cowboy hat—to reimagine Lon Megargee’s iconic painting, The Last Drop From His Stetson. First conceptualized a century ago, the work was originally no more than an advertisement. Over the years, however, it’s come to embody the so-called Cowboy Ethos: one of respect, compassion, integrity, and a bond between man and the world around him. It’s no doubt an idealized version of the reality of Westward expansion: A hardworking man, kneeling in the dirt under open sky, offers his canteen’s last to a brown-and-white steed. Thus was the case with much of the work that characterizes the movement—propaganda seducing young men toward the new frontier, contributing to an idyllic, up-by-bootstraps narrative promising adventure and self-determination.

“They represent the rugged individuals who carved out a life for themselves in the new Western frontier—a way of life that has been romanticized, representing the American Spirit.”

“I wouldn’t say that my work complicates the cowboy’s position in American art history,” Blackshear says. “It just tells the truth of what has been hidden from American culture and the history books.” His rendition of The Last Drop features a Black cowboy, standing upright, gazing at the viewer as he tends to his horse. “Let’s be real,” the artist goes on, “the truth is, white men working on ranches were called ‘cowhands,’ and Black men working on ranches were called ‘cowboys.’ That’s where the name came from.”

Blackshear’s work is a modernization of the story Megargee put forth. It’s a personification of the hidden Black cowboy—offering necessary nuance to a tradition characteristically lacking in it. “I wanted to stay true to the original concept, but with a different vision,” he continues. “I am known for painting personalities. I would hope that this version causes one to want to know more about this cowboy, as an individual.”

Having been an illustrator for upwards of 40 years, Blackshear’s work traverses genres: He’s produced drawings for Disney and Universal, and National Geographic; designed 30 US postage stamps; been inducted into the Society of Illustrators’ Hall of Fame. His allegiance to the world of Western art harkens back to nostalgia, and a drive to cast what’s legendary in contemporary light. “This generation’s men of courage are superheroes with capes,” he says. “For my father’s generation—and when I was a little kid—heroes wore cowboy hats. They represent the rugged individuals who carved out a life for themselves in the new Western frontier—a way of life that has been romanticized, representing the American Spirit.” There’s value in paying homage to these long-standing motifs, where history is cared for, in all its complexity.