Shay Roundtree developed a strong theater background in Atlanta. His breakthrough came when he auditioned for and won a role in Drumline (2002). Shay drove to Los Angeles alone with a few dollars in his pocket. After a month he got an audition and won the role of Junie Gatling on NBC's Kingpin (2003) . Shay got the part and has never looked back. He has appeared on five episodes of Kingpin and a national spot for Mountain Dew.