#2: Alan Jackson “Pop a Top” 1999 At the 1999 ceremony, George Jones, just months removed from a near-fatal car accident, was nominated for Single of the Year for his autobiographical ballad “Choices.” When CMA
#3: Charlie Rich Traditional vs. Mainstream Country 1975 Presenter Charlie Rich fanned the flames of an ongoing battle between country music’s traditional artists and the pop singers making waves in Nashville when he presented the
#4: Cindy Walker Hall of Fame acceptance speech 1997 Cindy Walker was inducted into the Hall of Fame in 1997, an honor that is still rare for women (only nine female artists currently hold membership).
#5: Reba McEntire Reba’s Red Dress 1993 For her 1993 CMA duet “Does He Love You” with Linda Davis, Reba McEntire asked stylist Sandy Spika to design a dress worthy of the moment. Mission accomplished.
#6: Mary Chapin Carpenter Opening Act 1990 In a rare coup for a new artist, Mary Chapin Carpenter earned a coveted performance slot on the 1990 show, and she used it to establish her identity
#7: Shania Twain Entertainer of the Year 1999 She’d long been an afterthought with the Country Music Association, failing to secure an award in her six-year career, but the organization righted past wrongs by honoring
#8: Faith Hill & Carrie Underwood Female Vocalist of the Year 2006 The CMAs experienced an unwanted (and many would argue, unwarranted) amount of attention in 2006, when an intended joke by Faith Hill cast
#9: Dolly Parton & Randy Travis Male Vocalist of the Year presentation 1988 Dolly Parton had a little fun with her presentation of the Male Vocalist of the Year award in 1988. First, she flirted
#10: Kathy Mattea AIDS Ribbon Presentation 1992 In a courageous move, Kathy Mattea drew attention to the AIDS epidemic at the 1992 ceremony. The entertainment industry was making special note of the disease by wearing
#11: Garth Brooks Entertainer of the Year speech 1991 The star of Garth Brooks was burning brighter than ever by the time of the 1991 ceremony. His win for the 1990 Horizon award was only