As a child, Stephen Holland drew as soon as he could hold a pencil. His talent was truly developed when he attended a high school that devoted half the day to art studies. Following his graduation from high school, Holland attended the Art Students League, The School of Visual Arts, and Pratt Institute, in New York City.

His passion for painting athletes was born of necessity – unable to afford live models when he was a young painter, Holland painted from sports magazines, where he “saw the male form in all its power and glory, expressed as contemporary gladiator.”

In 1989, Holland was named “Official Sports Artist of the Kings.” In 1993 he was named Sports Artist of the Year by American Sport Art Museum and Archives, and was tapped as an official artist for the 1996 Centennial Olympics.