The Boot Staff

Jackson's songs are some of the essential country songs of the last two decades.

The country star says his favorite memory from a previous CMA Awards ceremony is one from very early in his career -- and it's something that no one else saw.

On Oct. 15, 1969, Cash took home a record-setting five CMA Awards, including the night's highest honor, Entertainer of the Year.

"That was one of the greatest moments of my musical life."

I was walking out, and Emmylou walked up to me and ..."

On Oct. 11, 2003, McGraw's hit "Real Good Man" landed at the top of the charts.

On Oct. 8, 1994, Keith was undoubtedly raising a glass to toast to his success.

On Oct. 8, 1984, Murray was the queen of the CMA Awards.

McGraw and Hill first met at a Nashville radio station event, but things didn't start heating up until the blond beauty, a budding star at the time, was an opening act on McGraw's 1996 tour.

Oct. 5, 1994 was a day of celebration for Gill.