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.
1967
- 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.
1968
- Eddy Arnold
- Glen Campbell
- Johnny Cash
- Merle Haggard
- Charley Pride
Glen Campbell was a big awards favorite in 1968, with “By the Time I Get to Phoenix” and “Gentle On My Mind” both dominating the Grammy awards earlier that year. His win in this category foreshadowed bigger things, as he soon became a network variety star, while also scoring major country and pop hits with “Wichita Lineman” and “Galveston.”
1969
- Glen Campbell
- Johnny Cash
- Roy Clark
- Merle Haggard
- Charley Pride
Johnny Cash’s career was rejuvenated on the strength of two live prison albums, the latter of which produced the massive Shel Silverstein-penned smash, “A Boy Named Sue.” His victory came in a year that marked the beginning of his network variety show and had him dominating the country singles charts, spending ten combined weeks at #1 with “Sue” and “Daddy Sang Bass.”
1970
- Glen Campbell
- Johnny Cash
- Roy Clark
- Merle Haggard
- Charley Pride
Merle Haggard was a mainstay in this category from the beginning, nominated in each of the first seven years of the CMA Awards. His victory in 1970 coincided with his commercial peak, with signature hits “The Fightin’ Side of Me” and “Okie From Muskogee” helping him secure his only win in this category.
1971
- Merle Haggard
- Loretta Lynn
- Charley Pride
- Jerry Reed
- Conway Twitty
The last of four consecutive years where the Male Vocalist winner matched the Entertainer winner, Charley Pride went home with both awards in 1971. A winner on his fourth nomination, his popularity skyrocketed upon the release of “Kiss an Angel Good Morning,” which was climbing the charts at the time of the awards ceremony.
1972
- Merle Haggard
- Freddie Hart
- Loretta Lynn
- Charley Pride
- Jerry Reed
Instead of attending the awards show, Loretta Lynn’s husband Mooney went hunting. He didn’t want to watch her lose, but he missed watching history unfold as she became the first woman to win Entertainer of the Year. Lynn’s victory came on the heels of both solo hits like “One’s on the Way” and her popular duets with Conway Twitty.
1973
- Roy Clark
- Merle Haggard
- Tom T. Hall
- Loretta Lynn
- Charley Pride
Today he’s best known for Hee Haw, the country music variety show that he co-hosted, and it’s no coincidence that he won while the show was in its prime. Still, Clark is also one of country’s most admired legends, and his legacy goes far beyond the television show that showcased his extensive musical and comedic talents.
1974
- Roy Clark
- Mac Davis
- Loretta Lynn
- Olivia Newton-John
- Charlie Rich
The massive success of “The Most Beautiful Girl” and “Behind Closed Doors” helped Charlie Rich win this award. It was a long time coming, as Rich toiled in obscurity despite critical acclaim for his work. He would continue to score big hits on the country and pop charts over the next couple of years, at one point charting hits on different labels at the same time.
1975
- John Denver
- Waylon Jennings
- Loretta Lynn
- Ronnie Milsap
- Conway Twitty
John Denver’s victory in this race led to the most infamous moment in CMA history. Though he claimed it was due to medication later on, presenter Charlie Rich seemed to be making a furious statement against the pop crossover artists dominating country music when he opened the envelope, read it, and then lit a cigarette lighter and burned the envelope. The paper went up in flames as he derisively snarled the winner’s name, “My friend, Mister John Denver.” Poor John, accepting via satellite, was clueless to what was going on at the Opry house, and graciously accepted his award.
1976
- Waylon Jennings
- Ronnie Milsap
- Willie Nelson
- Dolly Parton
- Mel Tillis
This 2007 Hall of Fame inductee won this award just as he was changing labels. Tillis first gained notoriety for his remarkable songwriting talent, but eventually he was scoring enough hits to earn a place in this category. He would go on to have several more big hits after winning this award, earning another nomination in this category two years later.
1977
- Merle Haggard
- Waylon Jennings
- Ronnie Milsap
- Dolly Parton
- Kenny Rogers
Ronnie Milsap dominated the CMA Awards, becoming one of its most frequently honored performers during the formative years of the awards show. He finally won the big prize on his third try, powered by the success of his classic hit, “It was Almost like a Song.”
1978
- Crystal Gayle
- Ronnie Milsap
- Dolly Parton
- Kenny Rogers
- Mel Tillis
Her famous quote – “I’m not leaving country. I’m taking it with me” – must have held some water with the Nashville establishment, as Parton won this award at the height of her pop crossover success with “Here You Come Again,” the title track of her first platinum album. The front of her dress popped open before she went up to receive the trophy, prompting her to quip, “That’s what I get for trying to put fifty pounds of mud in a five pound bag.”
1979
- Crystal Gayle
- Barbara Mandrell
- Willie Nelson
- Kenny Rogers
- Statler Brothers
He never won Male Vocalist of the Year, but superstar Willie Nelson was given his due by the CMA in 1979 when they awarded him Entertainer of the Year. While it wasn’t his biggest year on the charts, residual goodwill from Stardust and his collaborations with Waylon Jennings helped carry him to victory.
1980
- Charlie Daniels Band
- Larry Gatlin & The Gatlin Brothers
- Barbara Mandrell
- Willie Nelson
- Kenny Rogers
She had a few big hits in 1980, like “Crackers” and “The Best of Strangers.” But it was her incredibly popular variety show with sisters Louise and Irlene that truly showcased her versatility as an entertainer, securing the first of two wins in this category.
1981
- Alabama
- George Jones
- Barbara Mandrell
- Oak Ridge Boys
- Kenny Rogers
Despite sharing the category with four artists who had never won this award, Barbara Mandrell became the first artist in CMA history to win Entertainer of the Year for the second time. Credit the continued popularity of her television show and the biggest hit of her career, “I Was Country When Country Wasn’t Cool”, which featured a guest turn by fellow nominee George Jones.
1982
- Alabama
- Barbara Mandrell
- Willie Nelson
- Oak Ridge Boys
- Ricky Skaggs
The band that laid the groundwork for all other country bands that followed, Alabama set a new bar for commercial success in the early eighties. The eligibility period included the release of their biggest-selling studio album, and also two of their signature hits: “Mountain Music” and “Love in the First Degree.”
1983
- Alabama
- Merle Haggard
- Barbara Mandrell
- Willie Nelson
- Ricky Skaggs
As their studio albums sold in the millions, every single Alabama released to radio was hitting #1, a stretch that would eventually include 21 consecutive chart-toppers. They repeated in this category on the strength of hits like “Dixieland Delight” and “The Closer You Get.”
1984
- Alabama
- Lee Greenwood
- Barbara Mandrell
- Ronnie Milsap
- Oak Ridge Boys
A mere three years after Barbara Mandrell made history by being the first artist to win two Entertainer awards, Alabama went her one better and won three. They remain one of only two acts to win this award three years in a row, doing so as their hits “Roll On (Eighteen Wheeler)” and “If You’re Gonna Play in Texas (You Gotta Have a Fiddle in the Band)” dominated the airwaves.
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- Alabama
- Lee Greenwood
- Reba McEntire
- Ricky Skaggs
- George Strait
Few country artists command as much respect as Ricky Skaggs, a consummate singer and musician. Skaggs’ victory in this category signaled the resurgence of traditional country music, as he was the first winner since 1976 to not have achieved crossover hits on pop radio.
1986
- The Judds
- Reba McEntire
- Willie Nelson
- Ricky Skaggs
- George Strait
One of the most popular new traditionalists of the mid-eighties, McEntire achieved her commercial breakthrough with “Whoever’s in New England”, which was aided in popularity by her first of many high-concept music video clips. McEntire would eventually become the most nominated woman in history, scoring ten nominations over eleven years.
1987
- The Judds
- Reba McEntire
- George Strait
- Randy Travis
- Hank Williams, Jr.
When Hank Williams, Jr. won the Music Video award the previous year, he reminded voters, “I make audio, too.” They finally got around to acknowledging his meaningful contributions to the genre, awarding him the first of two Entertainer trophies in 1987.
1988
- The Judds
- Reba McEntire
- George Strait
- Randy Travis
- Hank Williams, Jr.
Hank Jr. may have waited a long time for some CMA love, but once it came, it was in droves. He won Album of the Year the same night he repeated in this category. His biggest hit of the year, “Young Country”, featured guest appearances by up and comers like Highway 101 and Marty Stuart.
1989
- Reba McEntire
- Ricky Van Shelton
- George Strait
- Randy Travis
- Hank Williams, Jr.
Three years after his most recent Male Vocalist trophy, megastar George Strait was named Entertainer of the Year. He would go on to have one of his biggest years at radio, with two multi-week #1 singles in the twelve months that followed his victory.
1990
- Clint Black
- Kathy Mattea
- Ricky Van Shelton
- George Strait
- Randy Travis
While Randy Travis dominated the Male Vocalist race, George Strait was given his due again in the Entertainer category. He wore an Entertainer of the Year cowboy belt on the cover of Livin’ it Up, perhaps giving him good luck toward his second victory. He remains the most nominated in this category, and is only the second Hall of Famer to receive a nomination after being inducted into the Hall.
1991
- Clint Black
- Garth Brooks
- Vince Gill
- Reba McEntire
- George Strait
A mere year after winning the Horizon award, Garth Brooks was the Entertainer of the Year at the CMA Awards. He was breaking every sales record in the book by that point. Shortly before the ceremony, he became the first country artist to enter the overall album chart at #1, leading to a media frenzy that gained unprecedented exposure for both Garth and the genre he represented.
1992
- Garth Brooks
- Vince Gill
- Alan Jackson
- Reba McEntire
- Travis Tritt
Given that he was already the biggest-selling country artist the world had ever seen, it was no surprise that Garth Brooks won his second Entertainer of the Year trophy in 1992. His continued popularity was fueled by sold out live shows that soon led to network specials showcasing his unique brand of arena country.
1993
- Brooks & Dunn
- Garth Brooks
- Vince Gill
- Alan Jackson
- Reba McEntire
Vince Gill capped off an amazing night at the 1993 CMA Awards with his first victory in this category. It was his fifth win of the night, as he also took home Male Vocalist, Song, Album and Vocal Event. As he was also the show’s sole host, the collective exposure pushed him to multi-platinum sales.
1994
- Brooks & Dunn
- Garth Brooks
- Vince Gill
- Alan Jackson
- Reba McEntire
The soft-spoken Gill won for a second year, which was no big surprise given his widespread popularity in Music City. He also went home with Album and Male Vocalist the same night, giving him a stunning fourteen trophies in only five years.
1995
- Brooks & Dunn
- Garth Brooks
- Vince Gill
- Alan Jackson
- Reba McEntire
As one of the evening’s top nominees, Alan Jackson brought his parents as his special guests. After losing in every other category, he expressed relief that he finally won something, as going home empty handed would’ve been embarrassing. Jackson would eventually become one of the organization’s most awarded artists.
1996
- Brooks & Dunn
- Garth Brooks
- Vince Gill
- Alan Jackson
- George Strait
They were already winners of five CMA awards, due solely to their domination of the Vocal Duo category. But in 1996, they finally won another race, and it was a big one. Brooks & Dunn remain the only duo to win this award, with The Judds and Sugarland being the only other duos to receive nominations.
1997
- Brooks & Dunn
- Garth Brooks
- Vince Gill
- Alan Jackson
- George Strait
In a year when all five nominees had won this award before, it was Garth Brooks who returned to the winner’s circle, tying Alabama’s long-standing record of three victories in this category. Adding to the sense of déjà vu, this was the third year in a row where all five nominees were the same.
1998
- Brooks & Dunn
- Garth Brooks
- Vince Gill
- Tim McGraw
- George Strait
As hard as it is to believe that there were any records left for him to break by 1998, Garth Brooks shattered another one, becoming the first artist in the history of the CMA to win four Entertainer of the Year awards. By this time, Garth had already sold more than 60 million albums, and while he has yet to win this award again, he remains the top-selling solo artist of all time in the United States.
1999
- Garth Brooks
- Dixie Chicks
- Tim McGraw
- George Strait
- Shania Twain
The odds seemed against Shania Twain, as she had never won a CMA award before and the last woman to win was Reba McEntire thirteen years earlier. Fittingly, McEntire was on hand to present the trophy to Twain, who won on the strength of Come On Over, which eventually became top-selling country album of all time and the top selling album of the decade from any genre.
2000
- Dixie Chicks
- Faith Hill
- Alan Jackson
- Tim McGraw
- George Strait
The Dixie Chicks capped off a stunning three-year run at the CMA Awards with this victory, one of nine that they racked up since 1998. Within those three years, their first two albums each sold over ten million copies, and the band was widely credited for championing country radio and traditionalism while other top acts were crossing over to pop radio.
2001
- Brooks & Dunn
- Dixie Chicks
- Alan Jackson
- Tim McGraw
- George Strait
After winning two Male Vocalist and two Album of the Year honors in the previous three years, Tim McGraw finally won the CMA’s top award. It was a satisfying acknowledgment of an artist who’d had his talent underestimated in the first few years of his stardom, but built up a reputation for his stellar taste in choosing material.
2002
- Brooks & Dunn
- Kenny Chesney
- Alan Jackson
- Toby Keith
- George Strait
Jackson’s win in 1995 came as he was reaching his commercial peak. In the years that followed, Jackson remained a successful and well-respected artist that got less attention every year when it came time to hand out awards. Then came the one-two punch of “Where Were You (When the World Stopped Turning)” and “Drive (For Daddy Gene)”, both of which were viewed as the very embodiment of all that makes country music unique and essential. This was one of five awards he was honored with that night.
2003
- Brooks & Dunn
- Kenny Chesney
- Alan Jackson
- Toby Keith
- Tim McGraw
Although the ACM had chosen Toby Keith as their standard bearer a few months earlier, the CMA stuck with the previous year’s winner Alan Jackson. By 2003, Jackson had evolved into an elder statesman for the genre, but still managed to stay relevant with hits both clever (“It’s Five O’Clock Somewhere”) and poignant (“Remember When.”)
2004
- Brooks & Dunn
- Kenny Chesney
- Alan Jackson
- Toby Keith
- Tim McGraw
Chesney’s long dry spell at the CMA’s came to a satisfying end as the superstar collected both Entertainer and Album of the Year trophies. He had been charting for eleven years before finally winning his first CMA award.
2005
- Kenny Chesney
- Alan Jackson
- Toby Keith
- Brad Paisley
- Keith Urban
One of the most surprising and endearing wins in the history of this category, a shocked and humbled Urban accepted this award in New York City. He couldn’t have picked a better night to bring his Australian parents to the ceremony.
2006
- Brooks & Dunn
- Kenny Chesney
- Brad Paisley
- Rascal Flatts
- Keith Urban
It’s pretty rare to come back and win this award for a second time, as most multiple wins have been consecutive in this category. But Kenny Chesney joined Garth Brooks and Alan Jackson as the only other artists to pull it off when he won in 2006, a club that would later be joined by Taylor Swift.
2007
- Kenny Chesney
- Brad Paisley
- Rascal Flatts
- George Strait
- Keith Urban
Chesney entered the elite company of Garth Brooks, Alabama, and Alan Jackson with his third victory in this category. Rascal Flatts, meanwhile, became the first group since the Dixie Chicks to score back-to-back nominations, a feat also accomplished by Alabama and the Oak Ridge Boys.
2008
- Kenny Chesney
- Brad Paisley
- George Strait
- Sugarland
- Keith Urban
As Sugarland became only the third duo in history to receive a nomination and George Strait extended his record number of nominations to sixteen, Kenny Chesney tied Garth Brooks for the most wins in this category with his fourth victory. His popularity at radio and retail was remarkable, but it was Chesney’s highly attended summer stadium tours that earned him these wins.
2009
- Kenny Chesney
- Brad Paisley
- George Strait
- Taylor Swift
- Keith Urban
Taylor Swift both made history and prevented it with her win in this category. She simultaneously became the youngest artist ever and the first female solo artist in ten years to take home the prize. She also kept Kenny Chesney from becoming the sole all-time champion in this category, as he remains tied with Garth Brooks with four wins to date.
2010
- Lady Antebellum
- Miranda Lambert
- Brad Paisley
- Keith Urban
- Zac Brown Band
2010 shook up the category, with three first-time contenders in the running for the crown for the first time since 1981. Despite all the new blood, sixth time proved to be the charm for Brad Paisley, who finally won this award after five consecutive losses. Paisley’s persistent popularity helped him earn the nod in a year where the two previous winners weren’t even nominated.
2011
- Jason Aldean
- Brad Paisley
- Blake Shelton
- Taylor Swift
- Keith Urban
Thirty years after Barbara Mandrell became the first woman to win this award twice, Swift became the second to do so. She won the award on the strength of her third set, Speak Now, which showcased her growing maturity as a songwriter and her growing appeal beyond her teenage and young adult fan base.
2012
- Jason Aldean
- Kenny Chesney
- Brad Paisley
- Blake Shelton
- Taylor Swift
One of the most surprising wins in CMA history, few saw Blake Shelton’s victory coming. But it isn’t too surprising when you consider the number of artists who parlayed network television exposure into a win in this category. Perhaps in this new era of media saturation and minimal album sales, television may once again become a deciding factor when choosing the genre’s top star every year.
2013
- Jason Aldean
- Luke Bryan
- Blake Shelton
- George Strait
- Taylor Swift
George Strait’s farewell tour helped return him to the category for the first time since 2009, earning him a record-extending eighteenth career nomination. Strait joins previous winners Taylor Swift (2009, 2011) and Blake Shelton (2012) in attempting a return to the winner’s circle. Luke Bryan earns his first nomination, just months after winning the ACM trophy. Jason Aldean, meanwhile, is hoping to get lucky the third time around.
Facts & Feats
Multiple Wins:
- (4) – Garth Brooks, Kenny Chesney
- (3) – Alabama, Alan Jackson
- (2) –Vince Gill, Barbara Mandrell, George Strait, Taylor Swift, Hank Williams, Jr.
Most Consecutive Wins:
- (3) – Alabama (1982-1984), Kenny Chesney (2006-2008)
- (2) – Garth Brooks (1991-1992, 1997-1998), Vince Gill (1993-1994), Barbara Mandrell (1980-1981), George Strait (1989-1990), Hank Williams, Jr. (1987-1988)
Most Nominations:
- (18) – George Strait
- (12) – Alan Jackson
- (11) – Brooks & Dunn
- (10) – Reba McEntire
- (9) - Garth Brooks, Kenny Chesney
- (8) - Vince Gill, Merle Haggard, Brad Paisley
- (7) – Keith Urban
- (6) – Barbara Mandrell, Tim McGraw, Willie Nelson, Brad Paisley, Charley Pride, Keith Urban
- (5) – Alabama, Loretta Lynn, Ronnie Milsap, Kenny Rogers
Most Nominations Without a Win:
- (5) – Kenny Rogers
- (4) – Toby Keith, Randy Travis
- (3) – Jason Aldean, Waylon Jennings, The Judds, Oak Ridge Boys
Winners in First Year of Nomination:
Eddy Arnold (1967), Garth Brooks (1991), Glen Campbell (1968), John Denver (1975), Charlie Rich (1974), Taylor Swift (2009), Mel Tillis (1976), Shania Twain (1999), Keith Urban (2004), Hank Williams, Jr. (1987)
CMA Entertainers of the Year Who Have Never Won the ACM Award:
Eddy Arnold, Johnny Cash, Glen Campbell, Roy Clark, John Denver, Vince Gill, Alan Jackson, Tim McGraw, Ronnie Milsap, Brad Paisley, Charlie Rich, Blake Shelton, Ricky Skaggs, Taylor Swift, Mel Tillis, Keith Urban
ACM Entertainers of the Year Who Have Never Won the CMA Award:
Luke Bryan, Mac Davis, Mickey Gilley, Freddie Hart, Toby Keith, Kenny Rogers, Carrie Underwood
Good news for three legends of the genre, one of whom we lost to cancer only four years ago:
While Taylor Swift mania continues to grow, there’s another impressive accomplishment being achieved by two veterans of country music on the opposite end of the age spectrum.
My good friend and favorite sports blogger Charles Geier, of 
On Wednesday, February 4, the Country Music Hall of Fame will announce its newest members. The genre’s highest honor, induction into the Hall of Fame is bestowed upon the absolute best of country music. In 1996 the CMHOF developed a set of categories to sort candidates, an effort intended to recognize the great breadth of the genre.
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