Since its inception, the top honor an artist could be given at the Country Music Association awards is this one: Entertainer of the Year. Originally a revolving door of winners, the winner in early years was often not even nominated the following year. In 1981, Barbara Mandrell became the first artist to win the award twice. Alabama succeeded her with a three year run from 1982-1984. Fourteen years later, Garth Brooks became the first artist two win four times, a feat later matched by Kenny Chesney in 2008.
Here’s a look back at the award from the very beginning, along with some facts and feats about the category and its nominees.
- Bill Anderson
- Eddy Arnold
- Merle Haggard
- Sonny James
- Buck Owens
One year after being inducted into the Country Music Hall of Fame, Eddy Arnold was named the very first Entertainer of the Year at the inaugural CMA awards in 1967. Don’t assume it was a sympathy vote. Arnold had three #1 hits in the twelve months leading up to the ceremony, as he was in the middle of his impressive mid-sixties comeback, a period best defined by the 1965 classic, “Make the World Go Away.” He remains the only member of the Hall of Fame to win this award after being inducted.
Born and raised in Virginia, Shelton enjoyed the traditional country music of the sixties, but also had a taste for the pop of the same era and the gospel sounds that he heard in church every Sunday. He would draw from all three genres in his recording career, but his heart was always in traditional country music.
After playing in a band with his brother, he followed his girlfriend to Nashville in 1984. He played in nightclubs for a short time before being discovered by a local journalist. The media exposure led him to a deal with Columbia Records.
The hits come from all over the place here. Breakthrough hits from Trace Adkins and Carlene Carter join one-hit wonders Brother Phelps and George Ducas. And alongside crafty covers of songs by sixties rock band The Searchers and nineties country artist Joy Lynn White, you can also find tracks from three diamond-selling country albums.
400 Greatest Singles of the Nineties: #200-#176
Carrying Your Love With Me
1997 | Peak: #1
A traveler gets through his lonely nights on the sheer strength of love. It’s perhaps a little too saccharine for some, but the sweet melody and Strait’s understated vocals make the record work. – Tara Seetharam
1990 | Peak: #3
A man sits around in a bar “talking ’bout the good old times, bragging on how it used to be.” Simple premise, but the gorgeously melancholy melody and performance lift the record to Haggardly heights. – Dan Milliken
A lot of songs from both ends of the charts here, including a husband-and-wife duet that spent six weeks at #1.
400 Greatest Singles of the Nineties: #250-#226
I Meant Every Word He Said
Ricky Van Shelton
1990 | Peak: #2
At least the third song on this list about a guy mulling over romantic gestures he wishes he’d made to his former love, and the most traditional among those songs. You could easily imagine this one being a minor classic by a 60’s or 70’s legend, so close is its replication of that style. – Dan Milliken
I’m So Happy I Can’t Stop Crying
Toby Keith with Sting
1997 | Peak: #2
My hard-and-fast rule for Toby Keith: The sadder he is, the happier the listening experience tends to be. He’s all kinds of sad in this snapshot of post-divorce melancholia, reflecting on everything from unfair custody protocol to the greater motions of the universe. Even a gratuitous Sting cameo can’t detract from the single’s gloomy grandeur. – DM
You Ain’t Much Fun
1995 | Peak: #2
Toby Keith is also funny, though. What’s a man to do? Sobering up ain’t all that it’s cracked up to be from is perspective. Ever since he’s done so, his wife has been taking advantage of his increased functionality by giving him honey-do lists that he wasn’t ably tackling pre-sobriety. It’s enough to drive a man to drink. – Leeann Ward
This section begins with a song about a farmer and his wife and ends with one about Mama. Doesn’t get much more country than this!
400 Greatest Singles of the Nineties: #275-#251
Somewhere Other Than the Night
1992 | Peak: #1
About a woman who only feels truly appreciated by her husband when they’re having sex. That kind of says it all, doesn’t it? – Dan Milliken
Looking Out For Number One
1993 | Peak: #11
From his rocking side, Tritt is tired of trying to please everyone around him, including his demanding lover. As a result, he brashly declares that he’s going to make some changes, which will include looking out for himself. Get out of the way, because his ferocious performance makes him seem quite serious about his epiphany. – Leeann Ward
Let That Pony Run
1992 | Peak: #1
Gretchen Peters wrote the gorgeous song and Pam Tillis, in turn, beautifully sings it. The song is about Mary, a woman who is forced to start a new life after her husband confesses his infidelities with no apologies. The story is sad, it’s resilient, and it’s hopeful. – LW
I Just Want to Dance With You
1998 | Peak: #1
Any monotony in the verses is overcome by the song’s completely enticing rhythm and flavor. How can you not get lost in this? – Tara Seetharam