ACM Spotlight Series: Entertainer of the Year

For the final installment in our ACM Spotlight Series, we’ll be looking back at the decade’s recipients of the Academy’s highest honor, Entertainer of the Year. The Entertainer of the Year award recognizes the biggest country music star of the year. The official criteria states that artists who win have to have successful sales, outstanding concert ticket sales, and contribute to the country music industry. Starting with this year’s nominees we’ll look back at the winners and nominees of this coveted award.


2009

Kenny Chesney
Toby Keith
Brad Paisley
George Strait
Taylor Swift
Carrie Underwood
Keith Urban
Zac Brown Band

For the first year ever, the field of nominees for Entertainer of the Year has been expanded to eight nominees. Among this year’s crop of top entertainers are first time nominees Taylor Swift and Zac Brown Band. Also included are four past winners in Chesney, Keith, Strait and Underwood. Brad Paisley and Keith Urban are enjoying another nomination but they both have yet to win this award. For the third straight year, this year’s winner will be decided by fan votes, leaving one to think that Taylor Swift will walk away with the win.

2008

Kenny Chesney
Brad Paisley
George Strait
Carrie Underwood
Keith Urban

For just the seventh time in ACM history a woman took home the biggest award of the night. Carrie Underwood was chosen by fans and Academy members are 2008’s Entertainer of the Year becoming the first solo female artist to take home the award since Shania Twain during the 2000 awards show.

2007

Kenny Chesney
Brad Paisley
Rascal Flatts
George Strait
Keith Urban
In a bit of a controversial move, the Academy decided that the 2007 Entertainer of the Year would be decided by fan votes for the first time in ACM history. For the fourth straight year, Kenny Chesney was named Entertainer of the Year becoming the third artist to win four in a row, joining Garth Brooks and Alabama.
2006
Kenny Chesney
Brooks & Dunn
Tim McGraw
Rascal Flatts
George Strait
After having the biggest concert tour in country music, Kenny Chesney was once again crowned Entertainer of the Year for the third consecutive year.

2005

Kenny Chesney
Brooks & Dunn
Toby Keith
Rascal Flatts

Keith Urban

Kenny Chesney continued his dominance in 2005 and won his second consecutive Entertainer of the Year trophy beating out supergroup Rascal Flatts and his good friend, Keith Urban.

2004

Kenny Chesney
Brooks & Dunn

Toby Keith

Tim McGraw

Keith Urban

After two previous nominations, Kenny Chesney finally broke through to win his first Entertainer of the Year trophy. It would begin a historic streak of wins in this category for Chesney and cement him as one of the top entertainers in country music history.

2003

Kenny Chesney
Brooks & Dunn
Alan Jackson
Toby Keith
Tim McGraw

It’s interesting that the Academy has showered Toby Keith with plenty of nominations and awards, but the CMA’s have pretty much neglected him. In 2003, the ACM’s continued showering him with awards including his second straight Entertainer of the Year award.

2002

Brooks & Dunn
Kenny Chesney
Dixie Chicks
Alan Jackson
Toby Keith

In his third nomination, Toby Keith beat out other favorites like Alan Jackson and the Dixie Chicks to win his first Entertainer of the Year trophy. It was his only win during the 2003 ceremony, but it was the most prestigious one.

2001

Brooks & Dunn

Garth Brooks

Alan Jackson

Toby Keith
Tim McGraw

In a bit of an upset, Brooks & Dunn claimed their third Entertainer of the Year award beating out favorites like Toby Keith and Tim McGraw. Also in a surprising move, Garth Brooks received his first nomination in this category since his win in 1999.

2000

Brooks & Dunn
Dixie Chicks
Faith Hill
Toby Keith

George Strait

The late 90’s and early 2000’s were definitely dominated by the Dixie Chicks. The previous fall they picked up the CMA for Entertainer of the Year and they did it at the ACM’s during the 2001 awards show. This was only the sixth win by women in ACM history and the first all-female group to win.

1999

Dixie Chicks
Faith Hill

Tim McGraw

Sawyer Brown

Shania Twain

For the first time in the history of this category a husband and wife competed against each other. Also in an ACM rarity, three of the five nominees were women. But on that night in 2000, it was country-pop superstar Shania Twain that claimed Entertainer gold for the first time in her career.

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