CMA Flashback: Entertainer of the Year

Our CMA Flashback series concludes with the biggest honor of them all: Entertainer of the Year.

For a look back at the other major categories, visit our CMA Awards page.

Garth Brooks 22016

Garth Brooks

Luke Bryan

Chris Stapleton

Carrie Underwood

Keith Urban

On the evening that celebrated the fiftieth anniversary of the CMA Awards, Garth Brooks returned to the winner’s circle for the fifth time, breaking the all time record for wins in this category.

Luke Bryan

2015

Garth Brooks

Luke Bryan

Kenny Chesney

Eric Church

Miranda Lambert

Luke Bryan became the tenth artist in CMA history to win two Entertainer of the Year awards, taking home the award for the second year in a row. Meanwhile, four time winner Garth Brooks returned to the category for the first time in sixteen years, thanks to his wildly successful comeback tour.

Luke Bryan

2014

Luke Bryan

Miranda Lambert

Blake Shelton

George Strait

Keith Urban

Luke Bryan’s first win for Entertainer of the Year was also his first CMA Award.  He currently holds the distinction of being the only artist to win two Entertainer of the Year awards from the CMA without winning an award in any other category.

George Strait

2013

Jason Aldean

Luke Bryan

Blake Shelton

George Strait

Taylor Swift

George Strait’s victory this year was primarily due to his record-breaking farewell tour, and it produced one of the most enthusiastic standing ovations in CMA history. Before his win this evening, the longest gap between wins in this category was seven years. The gap between Strait’s previous victory and this one? 23 years.

Blake Shelton2

2012

Jason Aldean

Kenny Chesney

Brad Paisley

Blake Shelton

Taylor Swift

Blake Shelton dominated the Male Vocalist category from 2010-2014, and in 2012, he earned his only Entertainer of the Year trophy to add to his impressive collection.

swift

2011

Jason Aldean

Brad Paisley

Blake Shelton

Taylor Swift

Keith Urban

Taylor Swift’s second victory in this category made her the second woman in history to earn this award twice, exactly thirty years after Barbara Mandrell achieved the same feat in 1981.

Brad Paisley

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.

swift

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, as he remains tied with Garth Brooks for his four wins to date.

kenny-chesney

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.

Kenny Chesney

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.

Kenny Chesney

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. Taylor Swift and George Strait would later do the same.

keith-urban-blue-aint-your-color

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.

Kenny Chesney

2004

Brooks & Dunn

Kenny Chesney

Alan Jackson

Toby Keith

Tim McGraw

Chesney’s long dry spell at the CMAs 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 hist first CMA awards.

Alan Jackson

2003

Brooks & Dunn

Kenny Chesney

Alan Jackson

Toby Keith

Tim McGraw

The ACM had chosen Toby Keith as their standard bearer a few months earlier, but the CMA stuck with the previous year’s winner Alan Jackson, who joined the elite company of Garth Brooks and Alabama with his third Entertainer of the Year win.

Alan Jackson

2002

Brooks & Dunn

Kenny Chesney

Alan Jackson

Toby Keith

George Strait

Alan Jackson’s dominant sweep of the 2002 CMA Awards included his second win in this category, which he had first won in 1995. At the time, it was the longest gap between wins.

tim-mcgraw

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 big one. It was a satisfying acknowledgment of an artist who’d had his talent underestimated in the first few years of his stardom.

dixie-chicks

2000

Dixie Chicks

Faith Hill

Alan Jackson

Tim McGraw

George Strait

The 2000 CMA Awards belonged to the Dixie Chicks, who won Album, Vocal Group, and Music Video along the way to their Entertainer of the Year victory. The inclusion of Faith Hill in the category made 2000 the first time in twelve years that two female acts were nominated at the same time. It hasn’t happened again.

shania-twain

1999

Garth Brooks

Dixie Chicks

Tim McGraw

George Strait

Shania Twain

With her victory in this category, Shania Twain became the first woman in thirteen years to win Entertainer of the Year. This remains her only competitive CMA award to date.

Garth Brooks 2

1998

Garth Brooks

Brooks & Dunn

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.

Garth Brooks 2

1997

Garth Brooks

Brooks & Dunn

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.

1996

Garth Brooks

Brooks & Dunn

Vince Gill

Alan Jackson

George Strait

They were already winners of five CMA awards, thanks to their domination of the Vocal Duo category. But they finally won another race, and it was a big one. Brooks & Dunn remain the only duo to win this award, and only the second to be nominated, after The Judds.

Alan Jackson

1995

Garth Brooks

Brooks & Dunn

Vince Gill

Alan Jackson

Reba McEntire

Alan Jackson was relieved when he came up to accept his first Entertainer of the Year trophy, as it spared him some embarrassment. He’d brought his parents with him that night, and he’d lost every other race he was nominated for.

Vince Gill 2

1994

Garth Brooks

Brooks & Dunn

Vince Gill

Alan Jackson

Reba McEntire

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.

Vince Gill 2

1993

Garth Brooks

Brooks & Dunn

Vince Gill

Alan Jackson

Reba McEntire

Vince Gill capped off an amazing night at the 1993 CMAs 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.

Garth Brooks 2

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.

Garth Brooks 2

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 CMAs. He was breaking every sales record in the book by that point. His meteoric rise from newcomer to standard-bearer has only been matched by the Dixie Chicks, who also won Entertainer of the Year in only their third year on the charts.

George Strait

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 remains the most nominated in this category.

George Strait

1989

Reba McEntire

Ricky Van Shelton

George Strait

Randy Travis

Hank Williams, Jr.

Three years after his most recent Male Vocalist trophy, mega-star 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.

Hank Williams Jr

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 that he repeated in this category.

Hank Williams Jr

1987

The Judds

Reba McEntire

George Strait

Randy Travis

Hank Williams, Jr.

Four new traditionalists fell to a man who had been the glorification of Southern Rock for the previous decade. Williams had cracked the previous year when he won the Music Video award, “I make audio, too.” Finally, the CMA acknowledged him for his remarkable contributions to the genre.

reba-mcentire

1986

The Judds

Reba McEntire

Willie Nelson

Ricky Skaggs

George Strait

Reba McEntire has received more nominations for this award than any female artist in history. She won it on the same night that she collected her third of four Female Vocalist awards.

Ricky Skaggs1985

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 was a triumph for bluegrass music that would only be matched by the O Brother and Alison Krauss wins in the years to come.

Alabama

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 would remain the only act to win this award three years in a row until Kenny Chesney matched that streak from 2006-2008.

Alabama

1983

Alabama

Merle Haggard

Barbara Mandrell

Willie Nelson

Ricky Skaggs

How big were Alabama back in the early eighties? They were selling multi-platinum back when even the biggest country artists were lucky to go gold.

Alabama

1982

Alabama

Barbara Mandrell

Willie Nelson

Oak Ridge Boys

Ricky Skaggs

The massive success of Alabama at radio and retail helped them become the first group to ever win this award, and the only group other than the Dixie Chicks to ever take it home.

Barbara Mandrell 2

1981

Alabama

George Jones

Barbara Mandrell

Oak Ridge Boys

Kenny Rogers

Barbara Mandrell made history as the first artist ever to win this award twice.

Barbara Mandrell 2

1980

Charlie Daniels Band

Larry Gatlin & The Gatlin Brothers

Barbara Mandrell

Willie Nelson

Kenny Rogers

After losing Female Vocalist to Emmylou Harris, Mandrell could be forgiven for thinking her night would end without a win. Instead, she became the third woman to win Entertainer of the Year, after Loretta Lynn (1972) and Dolly Parton (1978.)

Willie Nelson

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.

dolly-parton

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.

Ronnie Milsap

1977

Merle Haggard

Waylon Jennings

Ronnie Milsap

Dolly Parton

Kenny Rogers

He has three Male Vocalist and three Album awards to his credit, but Milsap’s only victory in the biggest race came in 1977.

Mel Tillis1976

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. His daughter, Pam Tillis, would win Female Vocalist eighteen years later, making them the only parent-child combination to date to win major CMA awards.

John Denver

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.” Denver, accepting via satellite, was unaware of what was going on at the Opry house, and graciously accepted his award.

Rich_Charlie_002_c_MOA.jpg

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, a year after winning the award for Male Vocalist.

Roy Clark

1973

Roy Clark

Merle Haggard

Tom T. Hall

Loretta Lynn

Charley Pride

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, although industry respect for Clark’s talent as a musician was another big contributing factor.

loretta-lynn

1972

Merle Haggard

Freddie Hart

Loretta Lynn

Charley Pride

Jerry Reed

Her husband Mooney went hunting because he didn’t want to watch her lose. He missed watching history unfold before his eyes as Loretta Lynn became the first woman to win Entertainer of the Year.

Charley Pride1971

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.

Merle Haggard

1970

Glen Campbell

Johnny Cash

Roy Clark

Merle Haggard

Charley Pride

Merle Haggard swept the show in 1970, winning Male Vocalist, Single and Album of the Year, so it was no surprise when he triumphed in the final category of the night.

johnny-cash

1969

Glen Campbell

Johnny Cash

Roy Clark

Merle Haggard

Charley Pride

Johnny Cash dominated the CMA Awards in 1969. He wouldn’t win another major award from them during his lifetime, but was the posthumous victor for Single, Album, and Music Video in 2003.

Glen Campbell

1968

Eddy Arnold

Glen Campbell

Johnny Cash

Merle Haggard

Charley Pride

Glen Campbell not only won a ton of CMAs in 1968, he also was a big winner at the Grammys, a reflection his status as a pop-country star in his prime.

Eddy Arnold

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. Arnold had enjoyed three #1 hits in the twelve months leading up to the ceremony, as he was in the middle of his impressive mid-sixties comeback that had been fueled by the 1965 classic, “Make the World Go Away.”

Facts & Feats

Multiple Wins:

  • (5) – Garth Brooks
  • (4) – Kenny Chesney
  • (3) – Alabama, Alan Jackson, George Strait
  • (2) – Luke Bryan, Vince Gill, Barbara Mandrell, Taylor Swift, Hank Williams, Jr.

Most Consecutive Wins:

  • (3) – Alabama (1982-1984), Kenny Chesney (2006-2008)
  • (2) – Garth Brooks (1991-1992, 1997-1998), Luke Bryan (2014-2015), Vince Gill (1993-1994), Barbara Mandrell (1980-1981), George Strait (1989-1990), Hank Williams, Jr. (1987-1988)

Most Nominations:

  • (19) – George Strait
  • (12) – Alan Jackson
  • (11) – Garth Brooks, Brooks & Dunn
  • (10) – Kenny Chesney, Reba McEntire
  • (9) – Keith Urban
  • (8) –  Vince Gill, Merle Haggard, Brad Paisley
  • (6) – Barbara Mandrell, Tim McGraw, Willie Nelson, Brad Paisley, Charley Pride
  • (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, Miranda Lambert, 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)

Winners in Only Year of Nomination:
John Denver (1975), Charlie Rich (1974),  Shania Twain (1999)

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:
Jason Aldean, Mac Davis, Mickey Gilley, Freddie Hart, Toby Keith, Kenny Rogers, Carrie Underwood

3 Comments

  1. I don’t know what is more sad – the fact that Kenny Rogers never won this or that Kenny Chesney won it four times.

  2. Agree w caj on KC. Although I never watched a CMA show til the 90’s, I’m glad that John Denver won it in ’75. He was a great entertainer, singer and songwriter.

  3. Bob Dylan had it right when he sang “For the times, they are-a changin'”. It’s kind of amusing to look back at the furor caused by John Denver winning Entertainer of the Year in 1975, and then see him lionized by so many artists nowadays, a lot of whom were growing up in that era and heard something in John that Nashville so often seemed to miss. If anything, with his background in the 1960s folk music boom, which also gave rise to Linda Ronstadt and Emmylou Harris incidentally, Denver’s music is far closer to the truest roots of country than most anything that can be heard on the radio today (IMHO).

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