Bringing his love of Merle Haggard and Waylon Jennings more to the forefront, Modern Day Drifter followed two years later and became a Top Ten hit. In 2006, he returned with Long Trip Alone, a more polished effort that was commercial but not crass. Greatest Hits: Every Mile a Memory arrived in 2008. Although it was perhaps a bit early in his career for a compilation, it did contain his key charting singles and added in fan-selected live tracks as a bonus, making it a nice summation of Bentley's work up to that point. His fourth album, Feel That Fire, was released in early 2009, followed by the bluegrass-themed Up on the Ridge in 2010.
Bentley's sixth album Home, released in 2012, featured a dozen new songs that the singer road-tested on tour. It was an eclectic and varied affair, with guest spots from Little Big Town's Karen Fairchild as well as Tim O'Brien and Sam Bush, among others. Capitol issued his self-funded EP, Country and Cold Cans, that summer, and before long he had begun sessions for what would be his seventh full-length release for the label in 11 years. "Bourbon in Kentucky," a duet with Kacey Musgraves, was the first single from the sessions, but it flopped upon its June 2013 release, going no further than number 40 on the Billboard Country charts. A second single, "I Hold On," quickly followed and went into the Top Ten, but the lack of success for "Bourbon in Kentucky" was a factor in pushing back the release of Riser; it didn't appear until February 2014. ~ David Jeffries & Steve Leggett, Rovi