Special Report

50 Greatest Country Music Stars of All Time

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Merle Haggard

After surviving a troubled youth that saw him incarcerated in San Quentin, Merle Haggard went on to become one of country’s music’s legendary stars. From the 1960s to the 1980s, he had 38 No. 1 hits. One of his most famous songs, “Okie From Muskogee,” was released in 1969 at the height of the anti-war movement. Haggard reportedly gave two interpretations of the song: one was that it was a satire and the other that it was meant to be taken seriously as a political statement.

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Faith Hill

Having sold more than 40 million albums worldwide, Faith Hill is firmly established as a country superstar. But she also has enjoyed crossover success with the songs, “Breathe,” and “The Way You Love Me.” She’s performed several duets with husband, country star Tim McGraw.

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Alan Jackson

Singer-songwriter Alan Jackson began his career in the mid-1980s, and quickly skyrocketed to the top of the charts with his No. 1 single, “Here in the Real World,” in 1990. In 1991, he became a member of the Grand Ole Opry, and in 2017 was inducted into the Country Music Hall of Fame.

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Waylon Jennings

Waylon Jennings began performing at age 12, forming his own band, the Texas Longhorns. A founding member of the “outlaw country” movement, Waylon Jennings joined fellow stars Willie Nelson, Kris Kristofferson, and Johnny Cash to form the supergroup The Highwaymen.

His 1976 duet with Willie Nelson, “Good-Hearted Woman,” won the Country Music Association Vocal Duo of the Year award, and his collaboration the same year with Nelson, Jessi Colter, and Tompall Glaser on “Wanted! The Outlaws” became country music’s first Platinum album. For all his accomplishments, Jennings’s career might have been cut short: In 1958, he gave up his seat on the plane that crashed and killed Buddy Holly, Ritchie Valens, and J.P. “The Big Bopper” Richardson.

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George Jones

A true legend in country music, George Jones had 160 chart singles from 1955 to his death in 2013, including his best known song, “He Stopped Loving Her Today.” During his career, he battled alcoholism, but reached sobriety by 1999. He had a turbulent marriage to country singer Tammy Wynette, but both continued to perform together even after their divorce.