Watch Kenny Chesney: Greatest Hits (2001) Official Trailer

Country singer Kenny Chesney combines an old-fashioned cowboy persona with a few modern flourishes -- and that's an irresistible mix. When Chesney's "Greatest Hits" album was released in September 2000, it immediately took the No. 1 position on the charts. This video captures the country star in fine form in his music videos ("Me and You," "Don't Happen Twice" and "All I Need to Know").