Dierks Bentley burst onto the country music scene in 2003 when his self-titled debut album’s toe-tapping first single, “What Was I Thinkin’,” climbed to the top of the Billboard country charts. Since then, he’s had 20 country No. 1s – and counting – from nine studio albums, seven of which have reached the top spot on the U.S. country LP charts, and nearly all of which have been certified gold or platinum. Singer / songwriter / guitarist Bentley’s success might seem understandable, when hearing his note-perfect delivery of classic Music Row songs and seeing his blonde, square-jawed good looks, but it begins to feel a little less likely when considering some of the unpredictable and gutsy choices he’s made.