He's a little classier than twangy, but Vince Gill won't disappoint your down-home date. During his long-standing career, he's been honored with 20 Grammy awards, 18 Country Music Association honors and has made a pretty penny in album sales. He’s two-stepped into the Nashville Songwriters Hall of Fame with hits like "When I Call Your Name," "Look At Us," "I Still Believe In You" and "Go Rest High On That Mountain” and danced the do-si-do into to the Country Music Hall of Fame. He combines country and bluegrass to remind us which side of the Mason-Dixon we [mostly] belong to.