Rucker continued to tour and perform with Hootie & The Blowfish while working on his sophomore solo effort, a country album called Learn to Live. The album's first single, "Don't Think I Don't Think About It" jumped to to Top 20 on the Billboard charts in July of 2008, making Rucker the first African-American singer to reach the top of the country charts since Charley Pride in 1988. Rucker's newfound fame in the country realm also earned him an invitation to the Grand Ole Opry later that year, and his performance earned a standing ovation.
Rucker's single eventually hit number one on the country charts, and the album received platinum status in 2009. The album's next two singles "It Won't Be Like This For Long" and "Alright" also hit the top of the charts, making Rucker the first country music singer to have his first three singles reach number one since Wynona Judd in 1992. Rucker's album also gained the attention of critics, and earned him two Country Music Association award nominations in 2009, including Male Vocalist of the Year.
Continuing to thrive as a country music artist, Rucker released Charleston, SC 1966 in 2010, which topped the country album chart and featured the hit "This." His next record, True Believers (2013), helped him add another Grammy to his collection. The song "Wagon Wheel" earned him a win in the best country solo performance category in 2013. His most recent effort, 2015's Southern Style, was another success, lifted up by such songs as the title track and "Homegrown Honey."
In his private life, Rucker enjoys football, and hanging out with close friends Brad Paisley and Tiger Woods. He married long-time girlfriend Beth Leonard in 2000. The couple resides in Charleston, South Carolina, with their two children. Rucker also has a child with a former girlfriend.