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Chart Watch Extra: Country’s Top Prize: Entertainer Of The Year

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The odds are four out of five that history will be made when the Entertainer of the Year is announced at the Country Music Assn. Awards on Wednesday.

Kenny Chesney would become the first five-time winner in the history of the category-and the first act ever to win four years in a row.

Taylor Swift, 19, would become the youngest Entertainer of the Year winner ever-and the first female solo artist to win in this decade.

George Strait, 57, would become the oldest winner ever--and the act with the longest span of wins (20 years).

Keith Urban, who was born in New Zealand, would become the first person born outside of the U.S. to take the award twice.

The fifth nominee is Brad Paisley, who is co-hosting the annual CMA Awards telecast with Carrie Underwood. It would be Paisley's first win in the category, though he wouldn't establish any key records.

A total of 28 acts have walked off with the Entertainer of the Year award since the first CMA Awards in 1967. Twenty of them have been male solo artists. The roster of winners also includes five female solo artists (Loretta Lynn, Dolly Parton, Barbara Mandrell, Reba McEntire and Shania Twain), one female group (Dixie Chicks), one male group (Alabama) and one duo (Brooks & Dunn).

Garth Brooks and Kenny Chesney have won the most times (four times each).

Country Quiz: Who has been nominated for Entertainer of the Year the most times? That one's pretty easy. Here's a harder one: Who has been nominated for Entertainer of the Year the most times without winning? Answers below.

Here are 13 past Entertainer of the Year winners who established records when they won. They're listed in reverse chronological order.

Dixie Chicks. The trio, which won in 2000, is the only female group to win the award. Lead singer Natalie Maines was just 26 at the time, making her the youngest winner of this award ever (a record Swift may break this year). The Chicks' highest-charting Hot 100 hit to date is 2007's "Not Ready To Make Nice," which reached #4.

Shania Twain. In 1999, Twain, who was born in Canada, became the first person born outside of the U.S. to win. Twain's highest-charting Hot 100 hit was 1998's "You're Still The One," which reached #2.

Garth Brooks. Brooks set three records. In 1991, at age 29, he became the youngest individual artist ever to win. In 1997, he became the first male solo artist to win three times. In 1998, he became the first act to win four times. Brooks' highest-charting Hot 100 hit was 1999's "Lost In You" (in his Chris Gaines persona), which reached #5.

Brooks & Dunn. In 1996, Kix Brooks and Ronnie Dunn became the only duo ever to win this award. Brooks & Dunn's highest-charting Hot 100 hits were 2001's "Ain't Nothing 'Bout You" and 2003's "Red Dirt Road," both of which reached #25.

Hank Williams Jr. In 1988, Williams became the first male solo artist to win this award twice. Williams' highest-charting Hot 100 hit was his 1964 version of "Long Gone Lonesome Blues," which reached #67. The song was first a hit in 1950 for Williams' father, country legend Hank Williams.

Reba McEntire. McEntire, who was voted Entertainer of the Year in 1986, has been nominated for the award 10 times, more than any other female artist. (Barbara Mandrell is in second place with six nominations.) McEntire's highest-charting Hot 100 hit was 1999's "What Do You Say," which reached #31.

Alabama. The quartet set two records. In 1982, they became the first group ever to win this award. In 1984, they became the first three-time winners in the category's history. Alabama's highest-charting Hot 100 hit was 1981's "Love In The First Degree," which reached #15.

Barbara Mandrell. In 1981, Mandrell became the first two-time winner in the category's history. She had also won in 1980. Mandrell's highest-charting Hot 100 hit was a 1979 remake of Luther Ingram's R&B smash "If Loving You Is Wrong (I Don't Want To Be Right," which reached #31.

Charlie Rich. Rich was voted Entertainer of the Year in 1974, on his first and only nomination for the award. He was the first winner to experience that fate. (Two future Entertainer of the Years would join him: John Denver, the 1975 winner, and Shania Twain, the 1999 champ.) Rich's highest-charting Hot 100 hit was 1973's "The Most Beautiful Girl," which hit #1.

Loretta Lynn. In 1972, Lynn became the first woman to take this award. Lynn's highest-charting Hot 100 hit was 1971's "After The Fire Is Gone," a duet with Conway Twitty, which reached #56.

Charley Pride. In 1971, Pride became the only African American artist ever to win this award. Pride's highest-charting Hot 100 hit was 1971's "Kiss An Angel Good Mornin'" which reached #21.

Johnny Cash. In 1969, Cash became the first person to sweep the awards for Entertainer of the Year, Album of the Year and Single of the Year in one year. His winning album was Johnny Cash At San Quentin. His winning single was "A Boy Named Sue." That novelty smash was his highest-charting Hot 100 hit. It reached #2.

Eddy Arnold. Arnold set two records when he won in 1967. Arnold, a country star since 1945, became the first Entertainer of the Year. He was 49 at the time, which makes him the oldest winner ever in the category (a record Strait may break this year). Arnold's highest-charting Hot 100 hit was 1965's "Make The World Go Away," which reached #6.

Quiz Answers: This is George Strait's 17th nomination for Entertainer of the Year, which is by far the record. (Alan Jackson is in second place with 12 nominations.)

As for the act who has been nominated the most times without winning, it's a tie. Kenny Rogers and Brad Paisley have each been nominated in the category five times without taking home the prize. If Paisley wins this year, he'll leave Rogers as the unluckiest finalist in the history of the category. (I hope Kenny and Brad realize it's an honor just to be nominated. Which, of course, it is.)

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