He released a solo R&B album, Back to Then in 2002 on Hidden Beach Recordings but no singles from it charted. Six years later, Rucker signed to Capitol Nashville as a country music singer, releasing the album, Learn to Live that year. Its first single, “Don’t Think I Don’t Think About It”, made him the first black artist to reach number one on the Hot Country Songs charts since Charley Pride in 1983. (Ray Charles hit number one in March 1985 in a duet with Willie Nelson with “Seven Spanish Angels”. ) It was followed by two more number one singles, “It Won’t Be Like This for Long” and “Alright” and the number three hit “History in the Making”. In 2009, he became the first black American to win the New Artist Award from the Country Music Association, and the second black person to win any award from the association. A second album, Charleston, SC 1966, was released on October 12, 2010. The album includes the number one singles, “Come Back Song” and “This”.