Every Country Music Entertainer of the Year Since 1967

Alan Jackson won in 2002 the first of his two consecutive CMA Entertainer of the Year awards by defeating Brooks & Dunn, Kenny Chesney, Toby Keith, and George Strait. The single “Drive (For Daddy Gene)” spent 30 weeks on the Billboard Hot Country Songs chart and was No. 1 for four weeks. That was his most successful song of the 26 country No. 1 hits Jackson has recorded. Jackson’s “Drive” album was No.1 for six weeks.

Alan Jackson received his third and final (to date) Entertainer of the Year award in 2003, surpassing nominees Brooks & Dunn, Kenny Chesney, Toby Keith, and Tim McGraw. Although he had released his most recent album at the time, “Drive,” the previous year, its final single “That’d Be Alright” peaked at No. 2 in April 2003. Jackson also released his duet with Jimmy Buffett, “It’s Five O’Clock Somewhere,” this year.

Kenny Chesney gained CMA Entertainer of the Year honors in 2004, topping Brooks & Dunn, Alan Jackson, Toby Keith, and Tim McGraw. The song “I Go Back” was on the Hot Country Songs chart for 20 weeks and rose to No. 2. His album “When The Sun Goes Down” topped the country chart in 2004. Chesney has had 16 albums reach No. 1 on the country chart.

New Zealand-Australian Keith Urban won both Entertainer and Male Vocalist of the Year in 2005. Urban’s third U.S. solo album, “Be Here,” peaked at No. 1 on the Country Albums chart in October 2004. He would release another chart topping album, “Love, Pain & The Whole Crazy Thing,” in 2006.

Kenny Chesney regained CMA Entertainer of the Year honors in 2006, topping Brooks & Dunn, Brad Paisley, Rascal Flatts, and Keith Urban. “Summertime” was the big hit for Chesney that year, climbing to No. 1 and occupying the country chart top spot for five weeks. Chesney has had 23 country chart-toppers throughout his career. His album “LIVE: Live Those Songs Again” went to No. 1 on the Top Country Albums chart in 2006.