#21: Dixie Chicks
Sinnin’ and Winnin’
In 2000, the Dixie Chicks demonstrated their artistic integrity and their clear stranglehold on country music, buoyed by musical know-how and lyrical honesty and eloquence. Their near-sweep remains one of the most dominant performances by an act in a single ceremony.
With their four victories in 2000, the Texas trio was the true champion of the evening. They claimed the prestigious Entertainer of the Year trophy, becoming only the second group (Alabama) to win the award. They also took home Album of the Year for Fly, Vocal Group of the Year (for the third year running) and Video of the Year for their controversial “Goodbye Earl,” a clip that included cameos from Dennis Franz and Jane Krakowski as an abusive husband and his revenge-minded wife.
#22: Loretta Lynn
Entertainer of the Year win
With husband Doolittle absent (he feared for a disappointing evening), Loretta Lynn made history by becoming the first female to capture the award for Entertainer of the Year.
In 1971, Lynn began a professional partnership with Conway Twitty. As a duo, Lynn and Twitty earned a pair of #1 singles in the twelve months leading up to the 1972 ceremony, “After the Fire Is Gone” and “Lead Me On.” She also achieved a solo #1 with “One’s on the Way,” written by poet and songwriter Shel Silverstein. Her prolific chart presence also included “I Wanna Be Free,” “You’re Lookin’ At Country” and “Here I Am Again,” all Top Ten singles from the year preceding the awards show. So it was no surprise when Lynn shared the Vocal Event of the Year trophy with Twitty and nabbed her second win as Female Vocalist of the Year. The real shock was her victory in the top category, breaking the five-year stranglehold by male artists.
Lynn would secure eight CMA awards in her career, cementing her place as one of the finest women to ever sing or write country music. That status was confirmed by induction into the Country Music Hall of Fame in 1988.
Loretta Lynn, Hall of Fame induction (1988):
#23: Patty Loveless & George Jones
“You Don’t Seem to Miss Me”
Their partnership was a moment in hillbilly heaven, as one of the genre’s finest-ever traditional singers joined a terrific artist of the new generation in 1997. For her album Long Stretch of Lonesome, Patty Loveless enlisted the help of George Jones on the song “You Don’t Seem to Miss Me,” and its television debut occurred on the CMA show. Jones joined Loveless on stage, and the industry crowd voiced their approval of the perfect pairing. It was a soulful rendition of the song, a desperate plea to rekindle love’s flame. And only a couple of country music’s most heartbreaking voices could’ve given it the aching quality that writer Jim Lauderdale had intended.
#24: Ladies of the ’90s
The 1990s were a time of tremendous fortune for the leading ladies of country music, with the females in the genre mining more gold and platinum than ever and selling a record number of concert tickets.
The depth in talent was none more apparent than in the Female Vocalist of the Year category. Although only four men were named Male Vocalist of the Year between 1990-1999, eight different women received recognition as the year’s premier vocalist. Three women in particular, all diverse artists in an ever-changing genre, made their marks on the CMA Awards with their one win in the category.
#25: Willie Nelson & Julio Iglesias
“To All the Girls I’ve Loved Before”
The union of two styles of music can often produce dramatically interesting results, and so it was with the 1983 performance of “To All the Girls I’ve Loved Before,” an eventual #1 single for the Red Headed Stranger and the Latin pop icon Julio Iglesias. Although the song failed to meet with the highest critical acclaim, it was proof positive that genre boundaries can be eliminated with the talent of two strong artists.