Every Country Music Entertainer of the Year Since 1967

Eddy Arnold had been releasing country music records for decades by the time he won the CMA Awards’ first ever Entertainer of the Year award in 1967. He bested fellow nominees Bill Anderson, Merle Haggard, Sonny James, and Buck Owens for the honor. Arnold released two studio albums in 1967: “Lonely Again” and “Turn the World Around.”

Glen Campbell became CMA Entertainer of the Year in 1968, topping Eddy Arnold, Johnny Cash, Merle Haggard, and Charley Pride. That year, he released the first of his country No. 1 singles “I Wanna Live,” which occupied the top spot for three weeks. Six of his nine top-selling country albums were released in 1968.

In 1969, Johnny Cash released “Johnny Cash at San Quentin,” his second live album to be recorded in a prison after 1968’s “At Folsom Prison.” Both records hit No. 1 on the U.S. Country Albums chart and helped solidify Cash’s reputation as a rebellious giant of country music. The nominees that lost to Cash were Glen Campbell, Roy Clark, Merle Haggard, and Charley Pride.

Merle Haggard overcame a hardscrabble existence in California and repeated stints in prison to defeat Glen Campbell, Johnny Cash, Roy Clark, and Charley Pride for CMA Entertainer of the Year in 1970. The outlaw country singer’s big song that year was a double-sided hit “I Can’t Be Myself/Sidewalks Of Chicago” that spent 11 weeks in Billboard’s Hot Country Songs chart.

Charley Pride released two chart-topping albums in 1971: “I’m Just Me” and “Charley Pride Sings Heart Songs.” In addition to be declared Entertainer of the Year, he won the award for Male Vocalist of the Year. The other 1971 nominees for Entertainer of the Year were Merle Haggard, Loretta Lynn, Jerry Reed, and Conway Twitty.

Loretta Lynn, the coal miner’s daughter from Kentucky, was the CMA Entertainer of the Year in 1972, besting a field that included Merle Haggard, Freddie Hart, Charley Pride, and Jerry Reed. “Here I Am Again” spent 15 weeks on the Billboard Hot Country Songs chart, peaking at No. 3.

Roy Clark became CMA Entertainer of the Year on the strength of the success of the song “Come Live With Me,” which topped the country charts. Clark beat out Merle Haggard, Charley Pride, Loretta Lynn, and Tom T. Hall for the CMA honor. Clark established his celebrity status when he became one of the hosts of the primetime variety series “Hee Haw” in the late 1960s and early 1970s.

Few country performers enjoyed more success than Charlie Rich in the 1970s. CMA’s Entertainer of the Year in 1974 had a No. 1 that year with “There Won’t Be Anymore,” one of nine country No. 1 hits posted by the silver-haired singer. Two of Rich’s albums — “Very Special Love Songs’ and “There Won’t Be Anymore” — went to No. 1 on the country chart in 1974. Rich topped Roy Clark, Mac Davis, Loretta Lynn, and Olivia Newton-John for the CMA award.

John Denver released his album “Back Home Again” in 1974 to great acclaim. It featured some of the folk hero’s biggest singles, including “Thank God I’m a Country Boy,” “Annie’s Song,” and its title track, which also won Song of the Year. The singer’s most successful song of the year, however, was “I’m Sorry,” which was not included on the album. Denver’s competition for Entertainer of the Year consisted of Waylon Jennings, Loretta Lynn, Ronnie Milsap, and Conway Twitty.

“Good Woman Blues,” a No. 1 for two weeks on the Billboard country chart, helped propel Mel Tillis to CMA Entertainer of the Year over Waylon Jennings, Ronnie Milsap, Willie Nelson, and Dolly Parton. Tillis had six country chart-toppers all time on Billboard.

Ronnie Milsap won his sole Entertainer of the Year award in 1977 despite being nominated numerous times. He also walked away with the awards for Male Vocalist of the Year and Album of the Year for his album “Ronnie Milsap Live,” which was recorded at the Grand Ole Opry. The album spent 24 weeks on Billboard’s Top Country Albums chart, peaking at No. 2.

After several nominations for Entertainer of the Year, Dolly Parton finally received the CMA nod in 1978, ahead of Crystal Gayle, Ronnie Milsap, Kenny Rogers, and Mel Tillis. “Heartbreaker” was one of Parton’s 25 country No.1 hits throughout her career.

Iconic singer-songwriter Willie Nelson won his one and only Entertainer of the Year award in 1979, claiming victory over fellow nominees Crystal Gayle, Barbara Mandrell, Kenny Rogers, and the Statler Brothers. Nelson had released some of his most enduring albums by this point, including “Shotgun Willie,” “Red Headed Stranger,” and “Stardust.”

The country music hit maker and co-host of her own primetime variety show, Barbara Mandrell was the CMA Entertainer of the Year in 1980, buoyed by her country No. 1 “Years,” one of her six country chart-toppers. Mandrell bested Alabama, George Jones, Oak Ridge Boys, and Kenny Rogers for top CMA honors.

Barbara Mandrell won her second Entertainer of the Year award in 1981, one year after her first win. Mandrell also co-hosted the ceremony alongside singer-songwriter Mac Davis, and she performed with George Jones. Her song “Wish You Were Here” peaked at No. 2 on the Billboard Hot Country Songs chart in November of that year.

Alabama broke through as CMA Entertainer of the Year, topping Barbara Mandrell, Willie Nelson, Oak Ridge Boys, and Ricky Skaggs. The band had three No. 1 country songs in 1982, including “Take Me Down” and a No. 1 album, “Mountain Music.” Alabama has 33 country No.1 hits in all.

Alabama won again in 1983 after competing against Merle Haggard, Barbara Mandrell, Willie Nelson, and Ricky Skaggs for Entertainer of the Year. The band was also honored with the Album of the Year award for their “The Closer You Get,” which hit No.1 on the Country Albums chart that year. The album features No. 1 singles “Lay Down on Love,” “The Closer You Get,” and “Dixieland Delight.”

For the third straight year, Alabama was named the CMA Entertainer of the Year, besting Lee Greenwood, Barbara Mandrell, Ronnie Milsap, and the Oak Ridge Boys. Three of Alabama’s 33 country chart-toppers were released in 1984, including “If You’re Gonna Play In Texas.”

Country and bluegrass musician Ricky Skaggs broke Alabama’s three year streak of winning Entertainer of the Year in 1985, though the band was nominated, along with Lee Greenwood, Reba McEntire, and George Strait. Skaggs’ album “Country Boy” also peaked at No. 1 on Billboard’s Country Albums chart in 1985, staying in the top position for three weeks. The Ricky Skaggs band also won Instrumental Group of the Year for the third consecutive year.

Enduring country star Reba McEntire was named 1986 CMA Entertainer of the Year ahead of The Judds, Willie Nelson, Ricky Skaggs, and George Strait. McEntire had two country No.1 hits in 1986 — “Whoever’s In New England” and “Little Rock.”

Hank Williams, Jr. received the Entertainer of the Year award for the first time in 1987 — an honor that many felt was overdue. Williams’ album “Born to Boogie” topped the Country Albums chart that same year. The CMA would also recognize his video for “My Name is Bocephus,” off his previous album, “Montana Cafe,” granting it the award for Music Video of the Year.

Hank Williams, Jr. was named CMA Entertainer of the Year for the second consecutive year in 1988, defeating The Judds, Reba McEntire, George Strait, and Randy Travis. His “Young Country” single spent 15 weeks on the Billboard Hot Country Songs chart. Williams’ album “Wild Streak” went to No. 1 on the Billboard Top Country Albums chart and was one of his nine albums to top the country chart.

By 1989, George Strait had already charted enough hits to release numerous greatest hits compilations. He released the hugely popular album “Beyond the Blue Neon” that year, featuring chart-toppers “Baby’s Gotten Good at Goodbye,” “What’s Going on in Your World,” and “Ace in the Hole.” Strait’s competition for Entertainer of the Year in 1989 consisted of Reba McEntire, Randy Travis, Ricky Van Shelton, and Hank Williams, Jr.

George Strait, purveyor of traditional country music, was CMA Entertainer of the Year for the second straight year in 1990, besting Clint Black, Kathy Mattea, Randy Travis, and Ricky Van Shelton. Strait’s song “Love Without End, Amen” was No. 1 on the Hot Country Songs chart for five weeks and was one of two chart-toppers for Strait in 1990, with “I’ve Come to Expect It From You” the other No. 1. Strait had an eye-popping total of 44 No. 1 country hits throughout his career.

Garth Brooks received the first of his exceptional six Entertainer of the Year awards in 1991, following the release of his Certified 17x Platinum second album “No Fences.” The album featured numerous No. 1 country hits — “The Thunder Rolls,” “Two of a Kind, Workin’ On a Full House,” and “Friends In Low Places.” The latter song took home Single of the Year in 1991 and “No Fences” won Album of the Year.

Garth Brooks, the man in the black hat, was CMA Entertainer of the Year for the second straight year in 1992, winning the honor over Alan Jackson, Vince Gill, Reba McEntire, and Travis Tritt. “What She’s Doing Now” was No. 1 for four weeks on the Billboard’s Hot Country Songs chart. Brooks also had another chart-topper that year, “The River.” Brooks has had 19 country No. 1 hits.

Vince Gill won Entertainer of the Year in 1993 among a field of ’90s country royalty, including Brooks & Dunn, Garth Brooks, Alan Jackson, and Reba McEntire. Gill also won Album of the Year for his “I Still Believe In You,” which peaked at No. 3 on Billboard’s Country Albums chart.

Vince Gill got back-to-back CMA Entertainer of the Year honors, topping Brooks & Dunn, Garth Brooks, Alan Jackson, and Reba McEntire in 1994. Gill’s single “What The Cowgirls Do” rose to No. 1 on Billboard’s Hot Country Songs chart. His album “I Still Believe in You” cracked the top-10 for country albums in 1992.

Alan Jackson had just released his No. 1 album “Who I Am” when he won Entertainer of the Year. The record included some of Jackson’s biggest hits, including “Summertime Blues,” “Livin’ on Love,” “Gone Country,” and “I Don’t Even Know Your Name.” The other nominees for the award in 1995 were similar to those in other years during this period: Brooks & Dunn, Garth Brooks, Vince Gill, and Reba McEntire.

Country pair Brooks & Dunn defeated Garth Brooks, Vince Gill, Alan Jackson, and George Strait to be CMA’s Entertainer of the Year in 1996. The single “My Maria” spent 20 weeks on the Billboard Hot Country Songs chart and was No. 1 for three weeks. Brooks & Dunn had a slew of hits in the ’90s, and 20 songs were country chart-toppers.

Five years after his 1992 win, Garth Brooks was honored as Entertainer of the Year for the third time. Brooks also released that year his album “Sevens,” which featured two No. 1 country hits with “Longneck Bottle” and “Two Piña Coladas.”

Hit machine Garth Brooks made it two consecutive CMA Entertainer of the Year victories in 1998. The single “To Make You Feel My Love” went to No. 1, one of the artist’s 19 singles to top the country charts. Brooks also had two albums reach No. 1 on the country chart in 1998.

Shania Twain was still releasing singles from her massively successful 1997 album “Come On Over” in 1999. In total, 12 of the album’s 16 tracks were released as singles. By the end of 1999, the record would be certified 16x Platinum, eventually being certified double-diamond. Other Entertainer of the Year nominees were Garth Brooks, Dixie Chicks, Tim McGraw, and George Strait.

Before they courted controversy with remarks about President George W. Bush and the Iraq War, the Dixie Chicks won the CMA Entertainer of the Year award in 2000, topping Faith Hill, Alan Jackson, Tim McGraw, and George Strait. The group’s single “Cowboy Take Me Away” was No. 1 for three weeks.

Tim McGraw won his sole Entertainer of the Year award to date in 2001. That same year, he released his album “Set This Circus Down,” which would spend six weeks at the No. 1 position on Billboard’s Country Albums chart. The album included the chart topping hits “Grown Men Don’t Cry,” “Angry All the Time,” “The Cowboy in Me,” and “Unbroken.”

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.

Kenny Chesney scored his third Entertainer of the Year award in 2007, triumphing over the likes of Brad Paisley, Rascal Flatts, George Strait, and Keith Urban. That year also saw the release of his album “Just Who I Am: Poets & Pirates,” which spent 78 weeks on the Country Albums chart, peaking at No. 1.

Kenny Chesney returned as CMA Entertainer of the Year for a third straight year, besting Brad Paisley, George Strait, Sugarland, and Keith Urban. “Better As a Memory” was the hit single for Chesney, and it was one of his 23 songs that have topped the country chart for his career thus far.

Two years after receiving the New Artist award — then titled the “Horizon Award” — Taylor Swift secured the title of Entertainer of the Year. Her No. 1 album “Fearless” won Album of the Year, “Love Story” won Music Video of the Year, and Swift also walked away with Female Vocalist of the Year.

The often mirthful Brad Paisley was CMA’s Entertainer of the Year in 2010, winning out over Lady Antebellum, Miranda Lambert, Keith Urban, and Zac Brown Band. Paisley had two country No. 1 hits in 2010 — “Water” and Anything Like Me.” All told, Paisley has posted 18 country chart-toppers.

Taylor Swift won her second Entertainer of the Year award in 2011, triumphing over Jason Aldean, Brad Paisley, Blake Shelton, and Keith Urban. Swift was still combining country with pop music on her 2010 album “Speak Now,” and the album spent a notable 13 weeks at No. 1 on the Country Albums chart.

Blake Shelton, who television viewers know as a coach on “The Voice,” won the 2012 CMA Entertainer of the Year by beating Jason Aldean, Kenny Chesney, Brad Paisley, and Taylor Swift. Shelton had two country chart-toppers in 2012 — “Drink On It” and “Over.”

Twenty-four years after his first win in 1989, George Strait again received the honor of Entertainer of the Year. In 2013 he released his No. 1-charting album “Love is Everything,” featuring the singles “Give It All We Got Tonight,” “I Believe,” and “I Got a Car.” The year marked Strait’s final time winning the award, to date.

Luke Bryan, who was a nominee for CMA Entertainer of the Year in 2013, won it in 2014, besting Miranda Lambert, Blake Shelton, George Strait, and Keith Urban. “Play It Again” was a country No.1 for nine weeks, and the song crossed over to reach No. 14 on the Billboard Hot 100. Bryan has had 11 songs reach No. 1 on Billboard’s Hot Country Songs chart.

Luke Bryan won Entertainer of the Year again in 2015. That year saw Bryan begin to wind down his party-country persona, as he released the final EP from his “Spring Break” series — “Spring Break… Checkin’ Out.” The album was a hit with fans, who sent it to No. 1 on the Billboard Country Albums chart.

Garth Brooks returned as CMA’s Entertainer of the Year, winning it for the fifth time, topping Luke Bryan, Chris Stapleton, Carrie Underwood, and Keith Urban. The country music hitmaker had two No. 1 albums in 2016 –” “Christmas Together” and “The Ultimate Collection.”

Garth Brooks won his most recent Entertainer of the Year award in 2017, outdoing other top performers Luke Bryan, Eric Church, Chris Stapleton, and Keith Urban. It was Brooks’ sixth time winning the award and third back-to-back win, having been declared Entertainer of the Year in 1991 and 1992, 1997 and 1998, and 2016 and 2017.

New Zealand native Keith Urban topped all country performers in 2018, winning the CMA Entertainer of the Year over Jason Aldean, Luke Bryan, Kenny Chesney, and Chris Stapleton. Urban’s song “Female” was on the Billboard Hot Country Songs chart for 14 weeks and reached No. 11. He’s had 16 country chart-toppers in his career. His album “Graffiti U” reached No. 1 in 2018.