1987
Entertainer of the Year
Hank Williams, Jr.

1988
Entertainer of the Year
Hank Williams, Jr.

1989
Entertainer of the Year
George Strait

1990
Entertainer of the Year
George Strait

1991
Entertainer of the Year
Garth Brooks

1992
Entertainer of the Year
Garth Brooks

1993
Entertainer of the Year
Vince Gill

1994
Entertainer of the Year
Vince Gill

1995
Entertainer of the Year
Alan Jackson

1996
Entertainer of the Year
Brooks & Dunn