The Spanish conquistadors who ruled Mexico in the 16th century recruited native herdsmen on horseback to tend wild cattle on open rangeland. These "vaqueros" wore buckskin clothes, wide-brimmed hats, tall boots and spurs, and chaperajos (shaggy protective leggings), and carried la reata (rope). From that tradition came the itinerant cowpunchers, or cowhands, who drove Texas longhorn cattle to pasture and to market across the American southwest in the 1830s, and who established cattle ranches in the Canadian West in the 1880s. The term encompassed all cattle-handlers from simple livestock growers to moneyed English lords, Remittance Men and North-West Mounted Police ranchers.

The cowboy has been mythologized and popularized by entertainers who exhibited the cowboy skills of riding and roping at early "wild west" shows, later in rodeos and stampedes, and eventually in Hollywood movie westerns. Legendary cowboys in Canada include Guy Weadick, creator of the Calgary Stampede; John Ware, former black slave who ranched in southern Alberta; and rodeo competitors Pete Knight and Herman Linder.

See also Ranching History.