During 1882 he joined the Judith Basin Roundup as a night wrangler, this was the ideal situation for him as it gave him time to watch and sketch the cowboys at work in the daytime. He was fascinated with the Native American Indians, and visited them regularly, again sketching and documenting his travels.

He married Nancy Cooper in 1896 and they lived together in Montana for 46 years, he worked painting and sculpting in a log cabin next to the house and amassed a huge collection of weapons, horse jewelry, and cowboy memorabilia. He completed an amazing 4000 works during his lifetime.  His trade mark was to wear a sash rather than a belt, and many picture of him will show him in this attire. His love of the west has made him one of the most respected western artists of his time.