The next year, he auditioned for the Alvin Ailey American Dance Center (1983-1986) and received a scholarship to study under Alvin Ailey. He also received a merit scholarship for the Internationale Akademie des Tanzes in Köln, Germany (1984-1985) and was the recipient of a Presidential Scholar Award for the Arts (1986) from YoungArts. In 1986, Alvin Ailey personally invited him to become a member of his junior company, the Ailey Repertory Company. Richardson then danced with the Alvin Ailey American Dance Theater as a principal dancer from 1987 to 1994 before starting his own company with fellow Ailey dancer, Dwight Rhoden. In his seven years with the company, Richardson danced works by José Limón, John Butler, Elisa Monte, and many others.