Dierks Bentley

Dierks Bentley rocketed to the top of the country charts with his driving 2003 debut single "What Was I Thinkin'," opening up a career where he'd remain in the Top Ten year after year while simultaneously taking musical chances. Occasionally, Bentley dipped into his roots -- his 2010 album Up on the Ridge was largely devoted to bluegrass -- but his music was distinguished by how he blurred borders separating country, rock, and pop. Sometimes, Bentley's hits conveyed this sense of wanderlust -- this is especially true of 2005's "Lot a Leavin' Left to Do" and 2007's number one "...