Since the CMA Awards' inception in 1967, when Eddy Arnold nabbed the first-ever Entertainer of the Year trophy, there have been many deserving country singers awarded the title.
In some respects, the Country Music Association has always done better than a lot of organizations within the "Nashville machine" at incorporating women into its mission.
Jackson has been a fan-favorite singer for quite some time. But he isn't afraid to risk his popularity and take a stand for what he believes in -- even if it means going against what "the man" says.