The Highway Men

If you’re a country music fan like me you can probably rattle your favorite artists off the top of your head. So I thought it would be fun to share my list of the top 15 greatest country artists of all time and include videos of some their biggest hits.

There are so many amazing artists, new and old, in country music that this list is just the tip of the iceberg. Whether you agree or disagree, I’d love to hear your thoughts in the comments below.

Here we go:

15. Reba McEntire

Reba McEntire is one of the most successful country artists of all time. She began her career with Mercury Records in 1975 and released her first solo album in 1977.

Reba would go on to produce 29 studio albums, 40 number one singles, and 16 number one albums. She’s sold more than 85 million records worldwide.

She also holds the record for most CMA Award nominations for a female artist with 49 as well as ACM Awards with 45.

Some of Reba’s top songs include “Is There Life Out There,” “Turn on the Radio,” “I Keep on Lovin’ You,” and “Fancy.”

Reba McEntire Sings Fancy!

“Fancy” was originally written and performed by Bobbie Gentry in 1969. It tells the story of a woman overcoming heroine and poverty to become a successful courtesan.

Reba McEntire covered the song in 1990 on her Rumor Has It album.

14. George Strait

George Strait is known as the “King of Country.” Strait found success when his first single “Unwound” became a hit in 1981.

From there, he put out seven more albums in the 1980s where he was named “Artist of the Decade” by the Academy of Country Music and was inducted into the Country Music Hall of Fame. He won CMA Entertainer of the Year in 1989, 1990, and 2013.

Strait holds the record for most number-one hits on Billboard’s Hot Country Songs with 45 number ones. In total, he has 61 number-one hits. He’s sold more than 100 million records worldwide.

A number of his hits include, “Check Yes or No,” “Amarillo by Morning,” “Write This Down,” “Carrying Your Love with Me,” and “Troubadour.”

George Strait’s Troubadour

“Troubadour” was written by Leslie Satcher and Monty Holmes and recorded by George Strait. It was released in June 2008.

It tells the story of a troubadour reflecting on his life and feeling content in his accomplishments.

13. Dolly Parton

Dolly Parton was a successful songwriter before she made her album debut in 1967 with Hello, I’m Dolly. She’s had 25 songs reach number one on the Billboard country music charts.

Overall she had 41 career top 10 country albums and 110 career charted singles. She sold over 100 million albums worldwide.

Dolly was inducted into the Country Music Hall of Fame in 1999 and composed over 3,000 songs.

She is known for her songs, “I Will Always Love You,” “Jolene,” “9 to 5,” and “I Will Always Love You.”

Dolly Parton’s “I Will Always Love You”

“I Will Always Love” was written by Dolly in 1973 and debuted as a single in 1974. It was written as a farewell to her partner and mentor Porter Wagoner following Dolly’s decision to go solo.

12. Patsy Cline

Patsy Cline rose to fame in 1957 after an appearance on Arthur Godfrey’s Talent Scouts where she sang her hit song “Walkin’ After Midnight.” However, she first signed a record deal with Four Star Records in 1955.

Patsy was the first female country music star to headline her show. She was also the first female solo artist to be inducted into the Country Music Hall of Fame.

Her hits include “Walkin’ After Midnight,” “Crazy,” “Sweet Dreams,” and “I Fall To Pieces.”

Patsy Cline’s “I Fall To Pieces”

“I Fall to Pieces” was released in 1961 on Patsy’s studio album Patsy Cline Showcase.

The song was written by Hank Cochran and Harlan Howard, it tells the story about how a woman’s lover does not want them to be together and the woman falls to pieces every time she sees him.

11. Conway Twitty

Conway Twitty, born Harold Lloyd Jenkins, rose to fame in 1958 when an Ohio radio station decided to play “It’s Only Make Believe.” The ensuing success sent the record to number one and it sold over four million copies.

Twitty made his entry into country music in 1965, but it took him until 1968 to produce his first number one, “Next in Line.” Twitty won a number of awards including Grammys in 1971 and 1999.

His hits include, “Lead Me On,” “Louisiana Woman, Mississippi Man,” “I Can’t Love You Enough,” and “Hello Darlin’.”

Conway Twitty’s “Hello Darlin'”

“Hello Darlin’” was written and recorded by Conway Twitty. It was released in March 1970 on Twitty’s album, Hello Darlin.

The song is about a man who runs into an old flame and regrets how he acted in the relationship and how he still loves her.

10. Charley Pride

Charley Pride rose to fame after Chet Atkins heard a demo tape and got Charley signed to RCA Victor where he produced his first single, “The Snakes Crawl at Night.”

While the song didn’t chart, his third single, “Just Between You and Me,” became a breakaway success reaching number nine on the country chart.

Pride would go on to chart 52 top-10 hits, 29 of which hit number one. He was inducted into the Country Music Hall of Fame in 2000 and is a member of the Grand Ole Opry.

Pride’s hits include “Mississippi Cotton Picking Delta Town,” “Burgers and Fries,” “I Don’t Think She’s in Love Anymore,” and “Kiss an Angel Good Mornin’.”

Charley Pride’s “Kiss An Angel Good Morning”

“Kiss an Angel Good Mornin’” was written by Ben Peters and recorded by Charley Pride and released in October 1971 on Charley’s album Charley Pride Sings Heart Songs. The song instantly became a hit.

9. Tammy Wynette

Tammy Wynette, born Virginia Wynette Pugh, also known as the “First Lady of Country Music” rose to fame when producer Billy Sherrill signed her to Epic Records in 1966 when he needed a singer for “Apartment No. 9.”

After “Apartment No.9” just missed out being in the Top 40, Wynette’s third single “Your Good Girl’s Gonna Go Bad” went huge, peaking at number three. Wynette would go on to chart 20 number one songs.

Her hits include “D-I-V-O-R-C-E,” “My Elusive Dreams,” “I Don’t Wanna Play House,” and “Stand by your Man.”

Tammy Wynette’s “Stand By Your Man”

“Stand by Your Man” was written by Tammy Wynette and Billy Sherrill and recorded by Tammy and subsequently released in 1968.

It reached number one the country charts and stayed there for three weeks. It propelled Tammy Wynette to superstar status.

8. Randy Travis

Randy Travis, born Randy Bruce Traywick, came to fame after nightclub owner Elizabeth “Lib” Hatcher hired him as a cook and singer where he recorded an independent album Live at the Nashville Palace.

The album secured Randy a deal with Warner Bros. Records where in 1985 he released his single “On the Other Hand.” The song made it to 67 on the country charts. But his next single, “1982,” became a Top 10 hit.

Interestingly enough, Warner Bros. re-released “On the Other Hand” in 1986 where it became Travis’s first number-one hit.

Travis would go on to sell over 25 million records, earn 22 number-one hits, six number-one albums, and six Grammys.

His hits include “Three Wooden Crosses,” “I Told You So,” “Deeper Than the Holler,” and “Forever and Ever, Amen.”

Randy Travis’ “Forever And Ever, Amen”

“Forever and Ever, Amen” was written by Paul Overstreet and Don Schlitz and recorded by Randy Travis and released in 1987.

The song would go on to win a Grammy for Best Country & Western Song as well as Song of the Year from the Academy of Country Music. It sold nearly a million copies on digital alone.

7. Hank Williams

Hank Williams, born Hiram King Williams, began his music career in 1937 doing street performances outside the WSFA radio station. The producers eventually hired him to perform and host a 15-minute program.

He eventually formed his own band The Drifting Cowboys as backup, but it wasn’t until he signed with Acuff-Rose Music in 1946 for a six-song deal before he got his break. The deal with Acuff-Rose Music was leveraged for a deal with Sterling Records later that year.

He eventually signed with MGM in 1947 where he joined the Louisiana Hayride radio show.

Williams recorded 35 Top 10 singles and 11 that reached number one.

His hits include “Lovesick Blues,” “Move It on Over,” “Your Cheatin’ Heart,” and “I’m So Lonesome I Could Cry.”

Hank Williams’s “I’m So Loneseome I Could Cry”

Hank Williams wrote “I’m So Lonesome I Could Cry” in 1949. It was originally written for the words to be spoken instead of sung. It was inspired by Williams’s troubled relationship with his wife Audrey Sheppard.

Elvis Presley called the song “the saddest song I’ve ever heard.”

It reached #4 on the country chart in 1949.

6. Loretta Lynn

Loretta Lynn is the most awarded female country recording artist. She began her career when her husband Oliver “Doolittle” Lynn bought her a $17 Harmony guitar in 1953. Her first number one hit came in 1967 with “Don’t Come Home A-Drinkin’.”

She would go on to record 16 number one hits, with 70 overall charted songs. She was inducted into the Country Music Hall of Fame in 1988 and the Nashville Songwriters Hall of Fame in 1983.

She has recorded 70 albums, 54 studio albums, 15 compilation albums, and one tribute album. She has sold over 48 million albums.

Her hits include “You Ain’t Woman Enough,” “The Pill,” “One’s on the Way,” and “Coal Miner’s Daughter.”

Loretta Lynn’s “Coal Miner’s Daughter”

Loretta Lynn wrote and performed “Coal Miner’s Daughter” in 1969. It was released in 1970 and became one of her signature songs.

It tells her autobiographical story and describes her life in Butcher Holler as a coal miner’s daughter in rural Kentucky.

The song reached number 1 on December 19, 1970.

5. Willie Nelson

Willie Nelson wrote his first song at age seven and joined his first band at age ten. During high school, he toured with the Bohemian Polka as their lead singer and guitar player.

Nelson cut his first album, And Then I Wrote, in 1962. He signed with RCA Victor in 1964 and joined the Grand Ole Opry in 1965.

Willie Nelson would go on to chart twenty-five number one singles. His first was “Blue Eyes Crying in the Rain” off Nelson’s 1975 album Red Headed Stranger. Nelson recorded 68 studio albums, 10 live albums, and 37 compilations.

His hits include “To All the Girls I’ve Loved Before,” “If You’ve Got the Money I’ve Got the Time,” “Blue Skies,” and “Always on My Mind.”

Willie Nelson’s “Always On My Mind”

“Always On My Mind” was originally written by Johnny Christopher, Mark James, and Wayne Carson. It was first performed by Gwen McCrae and Brenda Lee in 1971.

There have been over 300 recorded version of the song by dozens of performers. It’s been recorded by Elvis Presley, John Wesley Ryles, Pet Shop Boys, Loretta Lynn, and Willie Nelson.

4. Waylon Jennings

Waylon Jennings got his first recording session in 1958 courtesy of Buddy Holly. He recorded “Jole Blon” and “When Sin Stops.” Holly then hired him as an electric bassist for his “Winter Dance Party Tour.”

Jennings eventually signed a record deal with Trend Records where he saw moderate success. He would then go on to record at A&M Records. Eventually Jennings found himself with RCA where he put out his album Leavin’ Town.

His cover of Gordon Lightfoot’s “(That’s What You Get) For Lovin’ Me” became his first top single.

Jennings was also the balladeer for The Dukes of Hazard. He composed and sang the show’s theme song and provided narration for the show.

In 2001, he was inducted into the Country Music Hall of Fame, however he chose not to attend.

Jennings composed 45 studio albums, 5 live albums, and 28 compilation albums. He had 16 number one singles in the United States.

His hits included “Luckenbach, Texas,” “The Wurlitzer Prize,” “Amanda,” and “Good Hearted Woman.”

Waylon Jennings’s “Good Hearted Woman”

“Good Hearted Woman” was written by Waylon Jennings and Willie Nelson in 1969. The song was composed in a Fort Worth, Texas, motel after Jennings read an advertisement about Ike and Tina Turner. He pitched the idea to Nelson over a game of poker where they completed the song.

The song debuted on Jennings’s 1972 album Good Hearted Woman. It peaked at number three on the Billboard’s Hot Country Singles. In 1975, he remixed the song, adding vocals from Willie Nelson and including fake crowd noise. The song went to number one.

3. Merle Haggard

Merle HaggardMerle Haggard got his start in San Quentin prison in the prison’s country band. After his parole in 1960 he sang and played guitar in Bakersfield. By 1962 he had signed with Tally Records and recorded five songs including his single “Sing a Sad Song.” I

n 1969, Haggard debuted his “Okie from Muskogee” single that earned him the Country Music Association’s Awards for Single, Entertainer, and Top Male Vocalist of the Year. He also won Album of the Year for Okie from Muskogee.

Haggard would go on to release 70 albums and 600 songs. He wrote 250 by himself. He had 38 number one singles.

His hits include “Swinging Doors,” “Sing Me Back Home,” “Same Train, a Different Time,” and “Mama Tried.”

Merle Haggard’s “Mama Tried”

Merle Haggard wrote and recorded “Mama Tried” and released he single in July 1968 on his album Mama Tried. It hit number one on the U.S. Billboard Hot Country Singles chart.

The song won the Grammy Hall of Fame Award in 1999 and was preserved in the National Recording Registry just 14 days before Haggard’s death.

2. George Jones

George “The Possum” Jones took a fancy to country music at age 7 and got his first guitar at 9. He launched his country music career in 1959 with a cover of J.P. Richardson’s, also known as the Big Bopper, “White Lightnin’.”

In 1962 he signed with United Artists and immediately put out one of his biggest hits “She Thinks I Still Care.” Jones would go on to record 134 singles, 10 of which became number ones. He put out 87 studio albums, three live albums, 43 compilation albums, and eight tribute albums.

His hits include “Tender Years,” “Walk Through This World with Me,” “The Grand Tour,” and “He Stopped Loving Her Today.”

George Jones’ “He Stopped Loving Her Today”

“He Stopped Loving Her Today” was written by Bobby Braddock and Curly Putman. Jones recorded the track in 1979 and released it in 1980. It was the first number one single for Jones in six years. It was number one for 18 weeks.

The song is widely considered the greatest country song of all time.

1. Johnny Cash

Johnny Cash broke onto the music scene when he visited Sun Records and auditioned for Sam Phillips in 1954. In 1955, Cash recorded “Hey Porter,” and “Cry! Cry! Cry!” at Sun.

Cash’s success would continue. His next record “Folsom Prison Blues” would break into the Country Top 5 and “I Walk the Line” would become a number one on the country charts.

Johnny Cash would go on to sell over 90 million records worldwide. He would record 165 singles with thirteen of them hitting number one. He released 96 albums including 55 studio albums and 6 live albums.

His hits include “There You Go,” “Ballad of a Teenage Queen,” “Understand Your Man,” and “God’s Gonna Cut You Down.”

Johnny Cash’s “God’s Gonna Cut You Down”

Johnny Cash’s “God’s Gonna Cut You Down” was released posthumously on “American V: A Hundred Highways” in 2006. Johnny’s version of the song has sold over 672,000 copies.

The song was originally a traditional folk song about warning sinners that they will face God’s judgment. Other titles for the song include “Run On” and “Run On for a Long Time.”

“God’s Gonna Cut You Down” has been preformed by Odetta, Elvis, and Moby, as well as Johnny Cash.

Share our list with your friends and family and let them know about the best country musicians of all time!

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