Growing up in Charleston, South Carolina, Rucker was exposed to the sounds of Otis Redding, Al Green, and Gladys Knight at an early age. Those R&B icons helped influence Hootie & the Blowfish's recordings, all of which featured Rucker's soulful baritone at the forefront, but it wasn't until his solo career that Rucker truly paid homage to the sounds of his youth. He initially planned to launch his solo career with The Return of Mongo Slade, which was scheduled for a summer 2001 release by Atlantic Records, but contractual changes prevented the album's release. A few months later, Rucker jumped ship for Hidden Beach Recordings, which then acquired the master recordings of his debut from Atlantic.

After making a cameo in the Farrelly brothers' film Shallow Hal, Rucker introduced his mellow, R&B-influenced music with 2002's Back to Then (essentially The Return of Mongo Slade with a different title), which featured collaborations with Jill Scott and Snoop Dogg. Rucker then returned his focus to Hootie & the Blowfish, releasing two albums with the group during the early 2000s before revisiting his solo career. This time, he opted for a country approach, and the twangy Learn to Live found an appropriate home among country music fans, who sent both the album and its flagship single, "Don't Think I Don't Think About It," to the top of the Billboard country charts. Two more singles also peaked at number one, pushing the album to platinum status within a year of its release. Rucker smartly stayed in the country mold for his follow-up album, Charleston, SC 1966, which appeared in fall 2010. His third solo album in a country vein, True Believers, followed in early 2013.