At 21, Remington inherited $9,000 from his father's estate, bought a small ranch in Kansas and with several other men eventually purchased a saloon in Kansas City. Even though he was cheated by his partners and lost considerable money, Remington had indeed been selling some paintings and drawings of his own, and he felt confident of his eventual success to return to New York, there marrying Eva.

However, with his inheritance gone, Remington found it hard to make a living on the sale of his paintings alone and began to illustrate for Outing Magazine, Harper's Weekly, Youth's Companion and Century. The Century articles were written by Theodore Roosevelt, and the collaboration was eventually published in book form. Immensely popular, the book contained ninety-nine Remington drawings and greatly furthered his career.

Remington lived in New York but repeatedly traveled west and was an observer of many historical events such as the battle at Wounded Knee. Not only did Remington record these events with pen, ink and paint, he wrote about them. The artists/journalist became a war correspondent to Cuba in 1898 where he witnessed the capture of San Juan Hill. Remington called himself a historian by virtue of his collected magazine articles, illustrated by himself, and wrote two historical novels, John Ermine of the Yellowstone and The Way of the Indian. He also completed illustrations for his friend Owen Wister's Done in the Open.

Because Remington is so associated with the American West, it may be surprising that he spent time with Augustus Saint-Gaudens and others in the artist colony in Cornish, New Hampshire. He almost bought property there, finding the fellowship of the community very stimulating.

Many of his earliest sketches and paintings depicted Apache conflicts and their great chief, Geronimo. These tightly rendered and dramatic depictions are accentuated by the brilliant and dusty colors reminiscent of the desert. Remington’s later style involved an increasing looseness in his brushwork; painted in short, occasionally broad strokes, one senses the dash and flair that Remington was able to transmit a story, elevating it to the status of art. “It is hardly possible to convey in words an accurate idea of the panic and terror spread throughout the country by Apaches on the warpath,” Remington wrote in an unpublished manuscript. “I have been in towns when yellow fever and cholera were first announced and have seen the panic-stricken flight of the people; but have never seen anything so terrify and paralyze people as the near approach of these bloodthirsty outlaws.”