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Love, Nat ( June 1854–1921), cowboy and author, was born in Davidson County, Tennessee, the son of Sampson Love and a mother whose name is unknown. Both were slaves owned by Robert Love, whom Nat described as a “kind and indulgent Master.” Nat Love’s father was a foreman over other slaves; his mother, a cook. The family remained with Robert Love after the end of the Civil War....

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Will Rogers Left, with Will Hays, c. 1925. Courtesy of the Library of Congress (LC-USZ62-83080).

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Rogers, Will (04 November 1879–15 August 1935), entertainer and social commentator, was born William Penn Adair Rogers near Oologah, Oklahoma, in what was then the Cooweescoowee District of Indian Territory, the son of Clement Vann Rogers and Mary America Schrimsher, Cherokee ranchers. Rogers County, which contains both Oologah, site of the historic Rogers home, and Claremore, site of the Will Rogers Memorial and Museum, is named after the prominent father, not the prominent son. “Uncle Clem” was a major player in Oklahoma politics before and after statehood (1907), serving as a judge, as a member of the Dawes Commission (to distribute Indian lands prior to statehood), and as the first local banker. Will’s loving wife, the former Betty Blake, whom he married in 1908, later remembered that “Will had everything he wanted. He had spending money and the best string of cow ponies in the country. No boy in Indian Territory had more than Uncle Clem’s boy.” (Yet being “Uncle Clem’s boy” could have its downside, too.)...

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Charles M. Russell. Photographic print, late nineteenth or early twentieth century. Courtesy of the Library of Congress (LC-USZ62-114799).

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Russell, Charles Marion (19 March 1864–24 October 1926), artist and author, was born in St. Louis, Missouri, the son of Charles Silas Russell, a wealthy businessman, and Mary Elizabeth Mead. As a child, Russell always preferred modeling in clay, drawing, and playing hooky. In 1879 his parents sent him to a military academy in New Jersey, but after a year they relented and allowed him to realize his dream of becoming a cowboy. He moved to the Judith Basin in Montana, where he tended sheep (1880), did chores for a hunter and trapper (1881–1882), and sketched western activities and scenery in his spare time. After a visit back in St. Louis for a month in 1882, he returned to the Great Northwest as a horse wrangler and cow puncher for several Montana cattlemen (1882–1893), but he continued to sketch and paint as much as he could....

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Siringo, Charles Angelo (07 February 1855–18 October 1928), cowboy, detective, and author, was born on Matagorda Peninsula, in Texas, the son of an Italian immigrant (first name unavailable) and Irish-born Bridgit White, farmers. His mother was widowed in 1856, married a drunkard named Carrier in 1868, lived with and then without him in Lebanon, Illinois, and next moved to St. Louis. Siringo had no schooling during the Civil War years in Texas, became a cowboy at age eleven, ran cattle for an employer named Faldien, worked at odd jobs in Lebanon (1868–1869), and was a bellhop for a year in a St. Louis hotel. After a fight with another employee he made his way to New Orleans, where he was befriended by a childless couple who sent him to school until a near-fatal knife fight, which he won, caused him to decamp for Texas in 1871....