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A sculptor, painter, ceramist and leather carver, Kittelson was a self taught artist who was born on a dirt farm in Arlington, South Dakota. As a child, John's earliest exposure to sculpture was playing with wood toys hand-carved by his father. He traveled to California and then to the Black Hills where he worked as a horse trainer and bronc rider. He and his wife settled in Cheyenne, Wyoming, where he worked as a carpenter and dabbled in painting and wood carving while working as a saddlemaker. He settled in Poudre Valley near Bellvue, Colorado and turned to making leather saddles and belts. His last work in leather was the trophy plague for the Cheyenne Frontier Days in 1957.
The previous year, he began painting in oil, and signed his work with a Tepee Bar brand. Then he turned serious about sculpting and did woodcarving, especially horses. The quality of his work earned him election in the Cowboy Artists of America in 1966. Four years later, he began working in bronze, which earned him more money.
For his woodcarving, he would buy an entire tree, usually a linden tree, and let it sit for several years so that it "cured". Then he had the wood kiln dried and went to work on it with a chisel.
In 1965, he sent in slides of his carvings to the Cowboy Artists of America and became one of the first fifteen members. Living in Cody, Wyoming, he became a full-time sculptor of wood, preferring to work with bass because it withstands temperature