Top country music artist the year you graduated high school

By Stacker

Published May 9, 2022 7:33 PM

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Top country music artist the year you graduated high school

From the iconic Nashville sound through to the smash single “Old Town Road”—which melds hip-hop with a traditional Western style—country music has always been wider-reaching than its reputation would suggest. Some of its foremost stars embody the genre’s evolution, but they also signify America’s cultural development at large. Take Dolly Parton, for example, who has more or less become an institution unto herself over the decades. And Taylor Swift is nothing if not an international force, with a fan base that went well beyond the country crowd even during her early years.

Despite the legacies of certain icons and its frequent interactions with other genres, country music does nevertheless remain something of a niche entity. This notion is only reinforced by the existence of two organizations, both of which were created to help spread awareness. One, the Country Music Association, was founded in 1958 primarily by Nashville industry members. The other is called the Academy of Country Music, and it was formed in 1964 as the Country & Western Music Academy with the participation of West Coast musicians.

Held in similar regard, both the ACM and the CMA dole out major awards on an annual basis. Among these awards is the prestigious Entertainer of the Year, which takes everything from radio play and album sales to music videos and concert performances—along with film and TV appearances and digital streams—into account. A reliable signifier of the biggest names in country music, the award simultaneously tracks the genre’s own unique evolution and lineage throughout the years.

Stacker put together a list of the top country music artist the year you graduated high school based on the winner of the Academy of Country Music’s top prize—the Entertainer of the Year award.

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1970: Merle Haggard

Haggard was serving time in San Quentin Prison when he caught a legendary live performance by Johnny Cash. He embarked on a music career soon after and broke through with the 1967 single “I’m a Lonesome Fugitive,” off the album of the same name. His ACM Entertainer of the Year award came on the heels of classic songs such as 1969’s “Okie From Muskogee.”

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1971: Freddie Hart

Freddie Hart was one among a number of artists who helped popularize the Bakersfield Sound, named for the eponymous California town. He beat out fellow icons such as Charley Pride and Loretta Lynn when taking home his ACM Entertainer of the Year award. His crossover hit “Easy Loving” won the CMA Song of the Year award two years in a row.

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1972: Roy Clark

Born into a gifted family, Roy Clark learned various instruments at a young age and performed with his musician father as a teenager. In addition to his successful music career, he hosted the popular variety show “Hee Haw” and also guest-hosted Johnny Carson’s “The Tonight Show.”

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1973: Roy Clark

While tightly associated with the country genre, Clark would often incorporate influences such as gospel and jazz. He was named Entertainer of the Year by both the CMA and ACM for 1973, and later inducted into the Country Music Hall of Fame.

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1974: Mac Davis

Mac Davis worked as a songwriter for artists such as Nancy Sinatra and Elvis Presley before going solo. His 1970 debut “Song Painter” kicked off a run of 19 albums over the course of 25 years. By the time he won his ACM award, he was hosting his own variety show and pursuing a simultaneous career in acting.

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1975: Loretta Lynn

Born Loretta Webb, this country starlet bought her first guitar for $17 in 1953. She scored her biggest hits in the late 1960s through to the 1970s both as a solo artist and in partnership with Conway Twitty. Her life story inspired the Oscar-winning biopic “Coal Miner’s Daughter.”

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1976: Mickey Gilley

This Mississippi-born singer and songwriter grew up playing music with cousins Jerry Lee Lewis and Jimmy Swaggart. His career rose and then waned throughout the 1970s, only to be revived by the 1980 film “Urban Cowboy.” Not only did the soundtrack feature Gilley’s remake of “Stand by Me,” but the movie itself was based on his namesake nightclub.

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1977: Dolly Parton

Ever the entertainer, Parton’s career spans multiple decades, genres, and mediums. Her iconic single “I Will Always Love You” topped the country chart on two separate occasions before Whitney Houston’s cover version dominated the Billboard Hot 100. She continues to earn a legion of achievements and accolades, including her 2022 induction into the Rock & Roll Hall of Fame.

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1978: Kenny Rogers

Rogers played with a jazz group called the Bobby Doyle Three and then the rock outfit First Edition before embarking on a solo career. He took home Top Male Vocalist awards around the same time that he was named Entertainer of the Year by the ACM. In 1980, he starred in a TV movie based on his hit single “The Gambler.”

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1979: Willie Nelson

A former U.S. Air Force serviceman and disc jockey, Nelson wrote hit songs for other artists through the 1960s. His solo career took off in the following decade, when he became a pioneer of the outlaw country subgenre. At the age of 89, he continues to tour.

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1980: Barbara Mandrell

Mandrell’s ACM Entertainer of the Year award was preceded by the chart-topping crossover hits “Sleeping Single in a Double Bed” and “(If Loving You Is Wrong) I Don’t Want to Be Right.” Loneliness and infidelity made for recurring themes throughout her musical career. She also appeared in various films and TV shows before retiring from show business in 1997.

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1981: Alabama

This influential band went by Wild Country before taking the name Alabama, the state in which they were formed. Unlike most country groups of their time, they were a self-contained unit of musicians. They signed to RCA and scored their first #1 country hit in 1980 with “Tennessee River,” winning a string of major awards soon after.

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1982: Alabama

Alabama scored eight #1 singles on the country chart from 1980 to 1982, including three cuts from their quadruple-platinum album “Mountain Music.” The same year they took home their second ACM Entertainer of the Year award, the band won their first CMA Entertainer of the Year award—and would become the first to do so three years in a row.

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1983: Alabama

This unstoppable band continued their hot streak into 1983, scoring a #1 country single with “Dixieland Delight.” In addition to winning Entertainer of the Year at both the ACM and CMA Awards (respectively), they won a Grammy for the album “Mountain Music.”

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1984: Alabama

Alabama released the certified quadruple-platinum “Roll On” before taking home their fourth ACM Entertainer of the Year award. The album hit #1 on the Billboard Top Country Albums chart, yielded four #1 singles on the Hot Country Singles chart, and reached #21 on the Billboard Hot 100.

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1985: Alabama

The most successful band in country music history kept the hits coming into 1985, once again dominating the charts with their album “40-Hour Week.” It featured the song “I Want To Know You Before We Make Love,” which would later become a smash single for Conway Twitty.

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1986: Hank Williams Jr.

The son of country music legend Hank Williams, Hank Jr. grew up performing his father’s classic hits and forging a similar sound. He adopted a rock influence and eventually developed his own style, breaking out in the 1970s. When a 1975 climbing accident resulted in two years of reconstructive surgery, he began sporting a signature beard, sunglasses, and hat. By the time he was named ACM Entertainer of the Year, he had already released 38 studio albums, including the #1 Billboard Country Album “Five-O” in 1985.

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1987: Hank Williams Jr.

After rebuilding his career in the wake of a near-fatal accident, Hank Williams Jr. began releasing material at an exponential rate. He scored 29 top 10 hits on the country singles chart from the late 1970s through to 1988. His 1985 album “Montana Cafe” topped the Billboard Country chart and cracked the Billboard 200 as well.

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1988: Hank Williams Jr.

Powered by hedonistic themes and a southern rock style, Hank Jr. once had nine albums on the Billboard Top Country Albums chart simultaneously. He won his third consecutive ACM Entertainer of the Year award and his second consecutive CMA Entertainer of the Year award in ’88. His certified Platinum album “Born to Boogie” received a Grammy nomination for Best Male Country Vocal Performance.

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1989: George Strait

Born in Texas and not afraid to show it, George Strait found his passion for country music while serving military duty in Hawaii. His career took off in 1981 when the “Urban Cowboy” country-pop craze was in full swing. By the time he was crowned ACM’s Entertainer of the Year in 1989, he had put together a string of nine consecutive platinum albums in the 1980s.

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1990: Garth Brooks

Garth Brooks first headed to Nashville in 1985, only to return to his native Oklahoma after just one day. He and then-wife Sandy Mahl went back to Music City in 1987 to much better results. His self-titled album and the 1989 hit single “Much Too Young (To Feel This Damn Old)” launched one of the most successful careers in music history.

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1991: Garth Brooks

Taking cues from the worlds of rock and pop, Brooks scaled country music up to arena size and ushered in a new era for the genre. His 1991 effort “Ropin’ the Wind” was the first-ever country album to top the Billboard Hot 200 chart. It was also his second album in a row to sell over 10 million copies within two years of its release.

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1992: Garth Brooks

By 1992, Garth Brooks was a cultural juggernaut with crossover appeal and millions of fans. He followed a multi-platinum Christmas album with “The Chase,” a personal and eclectic record that underperformed when compared to its predecessors—but still managed to top the Billboard 200 and Top Country Albums charts. Despite this potential setback, he continued to rack up major awards. In addition to Entertainer of the Year, Brooks would also win ACM Video of the Year for directing the music video to his hit single “We Shall Be Free.”

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1993: Garth Brooks

In fear of losing his core audience, Brooks returned to his rock-tinged country sound on the 1993 album “In Pieces.” It reached #1 on both the Billboard Hot 200 and Top Country Albums charts and was eventually certified Diamond by the RIAA. He embarked on his first world tour that same year and became the first country artist to sell out London’s Wembley Stadium.

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1994: Reba McEntire

The daughter of a world champion steer roper, McEntire and her siblings would sing at rodeos while growing up. Her solo performance of the National Anthem at the 1974 National Rodeo Finals caught the attention of entertainer Red Steagall, who invited her to Nashville. She slowly developed a following and broke out in the 1980s, also forging an acting career.

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1995: Brooks & Dunn

Kix Brooks and Ronnie Dunn joined forces in 1990 and delivered the blockbuster album “Brand New Man” the following year. Their signature hybrid of rock and honky-tonk made them preeminent icons of the line-dance craze with songs like “Boot Scootin’ Boogie.”

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1996: Brooks & Dunn

This wildly successful duo continued their commercial run with the release of the certified double-platinum album “Borderline” in 1996. Five of its singles appeared on the Hot Country Songs chart, including the #1 hit “My Maria.”

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1997: Garth Brooks

With his career still in full swing, Garth Brooks embarked on his second world tour in 1996. It lasted two years and included a free concert in New York City’s Central Park, which drew a crowd of nearly 1 million people. He released the hit-packed and Grammy-nominated studio album “Sevens” in November of 1997.

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1998: Garth Brooks

In 1998, Brooks released the best-selling live album in U.S. history. Titled “Double Live,” the album featured a collaboration with future wife Trisha Yearwood, who had also guested on his previous studio album. He went on to win Artist of the Decade at the ACM awards and then again at the 2000 American Music Awards.

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1999: Shania Twain

Born in Canada, Twain overcame an impoverished upbringing and other struggles before moving to Nashville and signing a record deal in the early 1990s. With help from husband and producer Robert “Mutt” Lange, she honed her crossover sound on 1995’s “The Woman in Me.” That was followed by the international blockbuster “Come On Over,” which remains the best-selling album in the history of country music.

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2000: Dixie Chicks

What began as a quartet of Texas-based bluegrass buskers became this country rock trio by the mid 1990s. Their 1999 album “Fly” debuted at #1 on the Billboard Hot 200 chart and made them the only female group in history to have two consecutive Diamond-certified albums. They dropped “Dixie” from their name in 2020 and now go by The Chicks.

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2001: Brooks & Dunn

Facing a minor slump in sales, Brooks & Dunn staged a comeback with the 2001 album “Steers & Stripes.” Among its trio of #1 country singles was the smash hit “Only in America.” The song was later used by George W. Bush and Barack Obama during respective election campaigns.

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2002: Toby Keith

This former farm boy broke through in 1993 with his debut single “Should’ve Been a Cowboy,” reportedly the decade’s most-played country song. He later released the single “How Do You Like Me Now?!” to crossover success. In the wake of 9/11 came his controversial but wildly popular song “Courtesy of the Red, White and Blue (The Angry American).”

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2003: Toby Keith

Keith continued to explore his surly brand of beer-guzzling patriotism on the 2003 album “Shock’n Y’all,” which sold over 4 million copies. He founded his own record label in 2005, which he named Show Dog Nashville, and later co-wrote, co-produced, and starred in the 2008 comedy film “Beer for My Horses.” Still in regular rotation by the 2010s, he was named Artist of the Decade at the 2011 American Country Awards.

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2004: Kenny Chesney

Raised in small-town Tennessee, Kenny Chesney self-released a demo album while still in college. He moved to Nashville in 1991 and performed regular gigs at a local honky-tonk before signing a publishing deal, followed by a recording contract. The 1999 album “Everywhere We Go” yielded two #1 country singles and brought him massive mainstream success.

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2005: Kenny Chesney

A crossover star, Chesney ran the full gamut from introspective ballads to unabashed party songs. He won the CMA’s prestigious Triple Crown along with a second consecutive ACM Entertainer of the Year award and numerous other accolades. His short-lived marriage to actress Renée Zellweger made him a temporary tabloid fixture.

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2006: Kenny Chesney

Chesney’s epic concerts were the stuff of legend by 2006, the year he released his first live album. He also collaborated with Tim McGraw on a version of the Tracy Lawrence single “Find Out Who Your Friends Are,” which became a radio hit.

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2007: Kenny Chesney

To the chagrin of Chesney, the ACM allowed fans to participate in the vote for Entertainer of the Year. He won the award but nevertheless criticized the new voting method as being little more than a coordinated marketing contest. The revised voting process lasted eight years before being discontinued in 2016.

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2008: Carrie Underwood

This modern phenom took the world by storm after winning the fourth season of “American Idol.” Her debut album “Some Hearts” garnered multiple awards and featured a slew of hit singles, including the crossover smash “Before He Cheats.” She’s sold over 66 million records worldwide and released 28 chart-topping singles to date.

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2009: Carrie Underwood

Underwood snagged a fourth Grammy award when her single “Last Name” won for Best Female Country Vocal Performance. She was also honored with ACM’s coveted Triple Crown, having won Top New Artist, Top Female Vocalist, and Entertainer of the Year during her career. Returning to “American Idol” as a celebrity guest, she performed a live rendition of Motley Crue’s “Home Sweet Home” for the 2009 season finale.

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2010: Taylor Swift

Any high school graduate from the last decade is familiar with Taylor Swift, whose ongoing crossover career is nothing short of historic. A musical prodigy from a young age, she signed a publishing deal at just 15 years old. She went on to win four Grammy Awards in 2010 alone, including Album of the Year for “Fearless.”

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2011: Taylor Swift

Swift’s 2010 album “Speak Now” explored personal relationships and helped her win a second consecutive ACM Entertainer of the Year award. She followed that with 2012’s “Red” and the #1 pop song “We Are Never Ever Getting Back Together.” The recent re-recording of previous material put a number of her singles back on the Hot Country Songs chart.

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2012: Luke Bryan

Hailing from Georgia, Bryan achieved initial success as a songwriter for artists such as Travis Tritt and Billy Currington. He broke out in 2007 with the album “I’ll Stay Me” and its lead single, “All My Friends Say.” His 2013 blockbuster album “Crash My Party” landed five singles at the top of Billboard’s Country Airplay chart.

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2013: George Strait

Five years after he was named Artist of the Decade by the ACM, George Strait took home his second ACM Entertainer of the Year award. With a whopping 60 chart-topping hits to his name, he holds the record for the most #1 songs on all charts of any artist in any genre.

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2014: Luke Bryan

Bryan topped the Billboard Hot 100 chart for the first time with a 2013 compilation of EPs titled “Spring Break … Here to Party,” and then did it again with the studio album “Crash My Party.” He beat out artists such as Garth Brooks and Miranda Lambert to win his second ACM Entertainer of the Year award. In 2018, he signed on as a judge for “American Idol.”

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2015: Jason Aldean

Born Jason Aldine Williams, this future superstar made his first public performance at the age of 14. He was ready to call it quits right before he signed with the independent label Broken Bow Records around 2005. His self-titled debut album featured three hit singles, including the country chart-topper “Why.”

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2016: Jason Aldean

Aldean performed his new single “Lights Come On” at the 2016 ACM Awards before it appeared on his seventh studio album, “They Don’t Know.” He embarked on his “Six Strings Circus Tour” that same year, co-headlining some shows with rock-rapper Kid Rock.

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2017: Jason Aldean

In 2017, Aldean was on stage in Las Vegas during what became the deadliest mass shooting in U.S. history. Thanks to the quick actions of a personal security guard and friend—who later sadly passed away—the country star was pulled to safety. He played “Saturday Night Live” the next weekend and released his eighth studio album, “You Make It Easy,” in January of the following year.

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2018: Keith Urban

Encouraged to pursue country music by his parents, Urban gained local recognition in Australia before moving to Nashville in the early 1990s. He struggled for years and eventually broke out in 1999 with his self-titled debut album. A successful career in both music and TV soon followed, as did a high-profile marriage to actress Nicole Kidman.

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2019: Carrie Underwood

Not long after she co-hosted the CMA Awards, Underwood tied with artist Thomas Rhett for ACM’s Entertainer of the Year award. It marked the first time that two artists were asked to share the honor. She’s the only female artist in history to have won the award three times.

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2019: Thomas Rhett

The son of famous singer-songwriter Rhett Akins, Rhett first topped the Billboard 200 chart with his 2017 album “Life Changes.” After a period of intensely personal, family-focused songwriting during the COVID-19 pandemic, he has already dropped one album in 2022 (“Where We Started”) and plans to release another one later in the year.

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2020: Luke Bryan

Bryan’s 2013 album “Crash My Party” won ACM’s very first Album of the Decade award in 2019. He released the follow-up “Born Here Live Here Die Here” in 2020 and watched it reach #5 on the Billboard 200 chart and #1 on the Top Country Albums chart.

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2021: Miranda Lambert

This Texas-born artist self-released a debut album and competed on “Nashville Star” by the time she was 18. Her career took off soon after and incorporated a number of peripheral genres, leading to blockbuster albums including 2007’s “Crazy Ex-Girlfriend.” In 2021, she won the Grammy for Best Country Album for “Wildcard.”

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