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As a child, Stephen Holland wore a brace on his leg which prevented him from playing sports and attending his neighborhood school with his friends. His handicap, in a curious way, apparently intensified his innate artistic talents. Instead of participating in sports, Holland sketched his family and friends playing. Fortunately, the special high school he later attended encouraged his art studies and Holland's talents blossomed. He subsequently studied at Art Students League, the School of Visual Arts and Pratt Institute, all in New York City.

Holland quickly gravitated toward drawing and painting sports themes. Unable to afford to pay for models, Holland drew inspiration from photographs he found in sports magazines. He was intrigued by the stories written about the athletes, their dedication and discipline to their sport. So fascinated by the athletes determination to win, Holland seems to have internalized the same inner strength as the athletes themselves and developed his own artistic prowess. His paintings are images of action, strength and purpose.

Holland received national attention when the American Sport Art Museum and Archives awarded him the honor of Sports Artist of the Year in 1993. His painting of Muhammad Ali for the Silver Anniversary of the Victor Award was later selected by Ali's wife for his 50th birthday party. His art also regularly appears on the Los Angeles King's Game Night hockey magazine. More recently Holland has been producing exciting celebrity portraits in addition to sports figures.