Dierks Bentley actually goes by his middle name; his first name is Frederick. Born in Arizona, Bentley spent his high school years at boarding schools and completed a year of college in Vermont, before transferring to Vanderbilt University in Music City. He worked at the Nashville Network (TNN, now Spike TV) before signing with Capitol Nashville and releasing his self-titled debut — the album that spawned his No. 1 single, “What Was I Thinkin'” and went platinum — in 2003. Two years later, Bentley married his wife Cassidy, received the CMA Horizon Award (now New Artist of the Year) and was inducted into the Grand Ole Opry; he’s one of the youngest members of the prestigious organization. The singer has been known to infuse his music with bluegrass sounds, and in 2010, he released a true bluegrass album, ‘Up on the Ridge’, which features many collaborations and hit No. 1 on Billboard’s Top Bluegrass Albums chart. Bentley also has his pilot’s license and owns his own plane — so his role as a pilot in the hilarious, award-winning “Drunk on a Plane” video wasn’t such a far-fetched idea.