On this day eleven years ago, Kenny Chesney took home CMA’s Entertainer of the Year Award. That was his third win for the coveted title in four years. It was in 2004 when the “Get Along” singer first bagged the organization’s Entertainer of the Year trophy. The following year, he lost the award to Keith Urban who also won the Male Vocalist of the Year Award.

In 2006 though, Chesney made a sweet comeback on the CMA stage taking the said title for the second time. Then again, on this date in 2007, he was able to defend this crown. This award made him the second artist with the most number of Entertainer of the Year awards next to Garth Brooks at that time. His success the following year allowed Chesney to match Brooks’ status. With each having a total of four Entertainer of the Year wins in 2008.

For his third Entertainer of the Year win, the Tennessee-native remained modest with his words.

“As much as tonight is about awards, I really believe that being able to stand up here is more about great songs, it’s more about the fans, it’s more about being onstage every night in front of a lot of people that really make it happen for me and the band,” he said. “This is my fourth time standing up here, and I’m really humbled tonight. I really appreciate it.”

Just about two months before Chesney claimed the said title, he released his album Just Who I Am: Poets & Pirates. The record embodied a shift toward a more gulf and Western sound featuring a number of “breezy, steel-drum island songs.” The album went to rank third place regarding the number of record sales after Kanye West’s Graduation and 50 Cent’s Curtis.

Other Recipients of CMA Entertainer of the Year Award

Since its inception in 1967, the CMA Awards honored more than 20 artists with the Entertainer of the Year title. It was the pioneer of the “Nashville Sound” Eddy Arnold who first won the trophy during the major awards show’s inauguration. On the other hand, the “Coal Miner’s Daughter” singer Loretta Lynn became the first female to win the prize in 1972. Meanwhile, Barbara Mandrell was the first female artist to take the accolade twice. To date, Garth Brooks holds the record for having the most number of Entertainer of the Year wins with a total of six.

This year’s CMA Awards are set to air on ABC on November 14. The event will be taking place at Nashville’s Bridgestone Area with Brad Paisley and Carrie Underwood as hosts. It will be the pair’s 11th year in a row to host the said ceremony.

Listen to Kenny Chesney’s “Everybody Wants to Go to Heaven” which he performed during the 41st CMA Awards night.