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His fourth album, Feel That Fire, was released in early 2009, followed by the bluegrass-themed Up on the Ridge in 2010. 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. Greatest Hits: Every Mile a Memory arrived in 2008. In 2006, he returned with Long Trip Alone, a more polished effort that was commercial but not crass.

Modern Day Drifter 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. It yielded the impossibly catchy single 'What Was I Thinkin'?' Capitol Records finally heard the artist, signed him, and released his self-titled debut, Dierks Bentley, in 2003. He landed a job at the TNN television network doing research on classic country music, and by night he worked on his demos. An all-night jam session recharged his batteries and he again started pursuing gigs.

It all changed when he walked into the Station Inn, a bar where the bluegrass faithful hung out.

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A love of the music inspired him to move to Nashville at the age of 19, but he quickly grew discouraged by the lack of public and professional interest coming his way.

Growing up in a non-musical family in Phoenix, Arizona, country singer Dierks Bentley got his country music education on his own, listening to records.