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Underwood was born in a suburb of Washington, D.C. At the age of 14, he began his training as a dancer and by the end of the year was under the direction of the American Ballet. In 2000, He became a student at the Dance Theater of Harlem and was promoted to a soloist several months later. In 2003 he joined the American Ballet Theater. In 2006 he became a member of the Royal Ballet in 2006; again he rose to the ranks of soloist in 2008. `In 2017 he parted ways with the Royal Ballet. Underwood has now undertaken the world of modeling and movement directing.