Shock Naue Ranks the Most Popular Country Singers Ever
Country music, born from the heart of American life during Ralph Peer’s historic 1927 Bristol sessions with pioneers like Jimmie Rodgers and the Carter Family, has always been a powerful storytelling medium. These early stars captured the essence of rural living, nostalgia, love, and loss, laying the groundwork for a genre deeply rooted in narrative. Through platforms like the Grand Ole Opry and tireless touring, country music established itself, chronicling the American experience like no other genre. This list explores the artists—from trailblazers to contemporary stars—who have defined and propelled the genre forward, becoming some of the Most Popular Country Singers known for their artistry, impact, and enduring appeal.
To compile this ranking of influential figures, Shock Naue references the extensive analysis by Billboard‘s editorial team, who selected top artists from a vast list spanning country music history. The focus remains primarily on mainstream country stars, acknowledging the genre’s core while recognizing its evolution. Factors considered included not just commercial success—a key indicator of popularity—but also artistry, longevity, and lasting influence. While the list naturally leans towards artists whose historical impact is already cemented, every singer included has significantly shaped and advanced country music, contributing to its rich tapestry and demonstrating why they resonate as the most popular and greatest figures in the genre’s history. Debates around rankings are inevitable, highlighting the incredible depth of talent within country music. Here, we present the definitive countdown.
100. Brothers Osborne
Alt: TJ and John Osborne of the popular country duo Brothers Osborne performing energetically on stage at the 2021 CMT Music Awards.
The Maryland-raised brothers have harmonized effectively during their initial decade as recording artists, merging TJ’s resonant baritone with older brother John’s skilled guitar work on songs exploring love and life. Achieving 11 top 40 country airplay hits, they’ve also secured a Grammy Award, six Academy of Country Music Awards, and five Country Music Association Awards. TJ further contributed to breaking barriers in 2021 by becoming the first major label country artist to publicly come out as gay. — GARY GRAFF
99. Maren Morris
The outspoken Texan Maren Morris burst onto the scene in 2016 with a dynamic blend of country, pop, and R&B, anchored by strong songwriting. She quickly gained popularity, earning top 10 Country Airplay hits like “My Church,” which won her a Grammy for best country solo performance, and “’80s Mercedes.” Morris has since achieved four No. 1 Country Airplay hits and a CMA Award for album of the year with Girl. Her versatility shines through collaborations like the dance-pop hit “The Middle” with Zedd and forming the country supergroup The Highwomen. Beyond music, she’s a powerful advocate for women, Black, and LGBTQIA+ artists within the country community, cementing her status as an influential modern country figure. — JESSICA NICHOLSON
98. Earl Thomas Conley
A key figure among 1980s country hitmakers, Conley was celebrated for his “thinking man’s country,” known for songs that delved sensitively into relationship psychology. However, this label sometimes overshadowed his adept melodic sense, which made his recordings highly singable for his era. His 1984 album, Don’t Make It Easy for Me, notably produced four No. 1 singles on the Country Songs chart, a first at the time. Though perhaps underappreciated, Conley’s influence persists, acknowledged by successors like Luke Bryan, who references “ETC” in his 2024 single, “Country Song Came On.” — TOM ROLAND
97. Dottie West
Before Dolly Parton famously partnered with Kenny Rogers, Dottie West collaborated with “The Gambler” on duets that defined the most commercially successful phase of her career. Inducted into the Grand Ole Opry in 1964, West had already won the first Grammy for best country & western vocal performance, female, for “Here Comes My Baby.” In the late 1970s, she transitioned from a traditional country style, applying her smoky vocals to pop- and R&B-infused tracks like “Are You Happy Baby?” and “A Lesson in Leavin’,” later covered by Jo Dee Messina. She was posthumously inducted into the Country Music Hall of Fame in 2018. — T.R.
96. Luke Bryan
Given an ultimatum by his father at 19—move to Nashville for music or lose his job on the family farm—Bryan secured a songwriting deal, co-penning Travis Tritt’s “Good Directions.” After honing his craft in clubs, he signed with Capitol Records and built a massive following with country party anthems, from 2007’s “All My Friends Say” to 2013’s “That’s My Kind of Night.” His popularity extended to multiple Spring Break albums, establishing him as a stadium headliner. Known for his friendly persona, signature dance moves, and distinctive baritone, the American Idol judge has amassed over 24 Country Airplay No. 1s, including the heartfelt “Drink a Beer,” making him one of the Most Popular Country Singers of his generation. — STEVE KNOPPER
95. Mel Tillis
Born in Florida, Tillis overcame a speech stutter and profound shyness when he sang. While many of his compositions, such as “Detroit City” and “Ruby, Don’t Take Your Love to Town,” became hits for other artists, he truly hit his stride as a performer in 1969. Embraced by the Outlaw movement, he enjoyed a run of nearly three dozen top 10 Country Songs hits into the mid-’80s, including chart-toppers like “I Ain’t Never,” “Good Woman Blues,” and “I Believe in You.” Father to performers Pam and Mel “Sonny” Jr., Tillis also appeared in films like The Cannonball Run, owned radio stations, and received a National Medal of Arts in 2012. — G.G.
94. Tennessee Ernie Ford
Tennessee Ernie Ford wearing plaid buffalo jacket while standing in field in 1961.
With his smooth baritone and affable humor, Tennessee Ernie Ford became a prominent figure in both music and media. He was widely known for his radio and television work, including The Ford Show on NBC (1956-61) and numerous acting roles, as well as his hit recordings. His cover of Merle Travis’ “Sixteen Tons,” along with “Mule Train” and his own “The Shotgun Boogie,” cemented his musical legacy. Ford achieved 22 top 20 country hits between 1949 and 1976, earned three stars on the Hollywood Walk of Fame (for radio, records, and television), and was awarded the Presidential Medal of Freedom. — G.G.
93. Rascal Flatts
Selling over 9 million copies of their first three albums starting in 2000, the trio of Gary LeVox, Jay DeMarcus, and Joe Don Rooney became country’s biggest act between the industry’s shift away from The Chicks in 2003 and Taylor Swift’s rise in 2006. Kicking off with “Prayin’ for Daylight,” and followed by massive hits like “Bless the Broken Road” and “What Hurts the Most,” the group enjoyed nearly two decades of smooth-harmonied success. Rascal Flatts ultimately sold over 23 million albums and 11 million concert tickets, solidifying their place among the most popular country singers and groups of the early 21st century. After a hiatus, they announced a 2025 tour. — S.K.
92. Vern Gosdin
Known as “The Voice” long before the TV show, Vern Gosdin was a commanding yet versatile singer and an early influencer on the West Coast country scene. Originally from Alabama, he moved to California in the early ‘60s, collaborating with artists like Chris Hillman of the Byrds before forming the Gosdin Brothers with his sibling Rex. After a short retirement, Gosdin achieved significant success, scoring 19 top 10 Country hits starting in 1977, including the poignant ballad “Chiseled in Stone.” Despite a stroke in 1998, he continued writing and performing until his death in 2009. — G.G.
91. Darius Rucker
Darius Rucker performs at the 2011 Allstate Fan Fest on Jan. 3, 2011 in New Orleans, Louisiana.
Arguably the most visible and successful Black country artist of the 2000s and 2010s, Darius Rucker established himself as a major force in the genre following his ’90s fame as the frontman of the diamond-certified pop-rock band Hootie & the Blowfish. His country career took off with 2008’s Learn to Live, the first of his four No. 1 albums on Top Country Albums. Rucker’s Southern charm, soulful voice, and accessible songs earned him multiple No. 1 singles, including “Alright,” “Wagon Wheel,” and “Beers & Sunshine.” As one of only five Black artists to win a country Grammy, Rucker is a vital figure in 21st-century country music. – KYLE DENIS
90. The Mavericks
Emerging from Miami, The Mavericks brought a fresh, invigorating mix of country, rock, and Latin influences—driven by lead singer Raul Malo’s Cuban-American heritage—that captivated Nashville in the early ‘90s. Known for their high-energy shows, exceptional musicianship, and Malo’s powerful, crystalline vocals (often compared to Roy Orbison), the band scored hits like “What a Cryin’ Shame,” “Oh, What a Thrill,” and “All You Ever Do Is Bring Me Down” (featuring Flaco Jimenez). However, The Mavericks’ true strength has always been their live performances, which continue to draw crowds today. – MELINDA NEWMAN
89. Kacey Musgraves
By the time Kacey Musgraves accepted the Grammy for Album of the Year in 2019 for Golden Hour, the Texas native had already dedicated over 15 years to her music career. Golden Hour, celebrated for its disco influences, wistful melodies, and poignant lyrics (also winning Best Country Album), showcased just a fraction of her artistry. Musgraves has consistently pushed for more progressive sounds and perspectives within country music. In 2013, she released the LGBTQIA+ affirming anthem “Follow Your Arrow.” A year later, she won Grammys for her album Same Trailer Different Park and the single “Merry Go Round,” which critically examines societal expectations placed on women. – TAYLOR MIMS
88. Ricky Skaggs
Skaggs began his career as a highly skilled instrumentalist in renowned bluegrass groups like the East Kentucky Mountain Boys (with Keith Whitley), Ralph Stanley’s Clinch Mountain Boys, and The Country Gentlemen. In 1981, he released Waitin’ for the Sun to Shine, his first major-label album, introducing a fusion of bluegrass and contemporary country that produced two Hot Country Songs No. 1s: “I Don’t Care” and “Cryin’ My Heart Out Over You.” Named CMA Entertainer of the Year in 1985, Skaggs became a pivotal figure in country’s neo-traditional movement, achieving 11 Country Songs No. 1s in the 1980s, including “Honey (Open That Door)” and “Uncle Pen.” He was inducted into the Country Music Hall of Fame in 2018. — J.N.
87. Faron Young
When the Country Music Hall of Fame initiated its medallion ceremony in 2001, Faron Young, known as the “Young Sheriff” after portraying a lawman in the 1955 film Hidden Guns, was posthumously inducted alongside Charley Pride. After serving in the Korean War, Young’s distinctive voice cut through AM radio static, leading to 40 top 10 country singles between 1953 and 1974, including five No. 1s. Among these was Willie Nelson’s early songwriting success, “Hello Walls,” now recognized by the Grammy Hall of Fame. Young also founded The Music City News, a leading country fan magazine for over three decades. — T.R.
86. John Anderson
Inducted into the Country Music Hall of Fame in 2024, this Apopka, Florida native is known for one of country music’s most distinctive voices and an exceptional ear for songs. Anderson paid his dues in Nashville, even working on the roof of the Grand Ole Opry House, before signing with Warner Bros. He found chart success with hits like “Wild & Blue,” “I’m Just an Old Chunk of Coal,” and the 1983 CMA Single of the Year, “Swingin.’” He experienced a career resurgence in the 1990s with popular tracks like “Seminole Wind” and the Country Songs No. 1s “Straight Tequila Night” and “Money in the Bank.” — DEBORAH EVANS PRICE
85. Travis Tritt
A key member of country music’s acclaimed Class of ‘89 alongside Clint Black, Garth Brooks, and Alan Jackson, Travis Tritt exploded onto the scene with the top 10 hit “Country Club.” He followed with a string of memorable singles like “Drift Off to Dream,” “Here’s a Quarter (Call Someone Who Cares),” “Anymore,” “I’m Gonna Be Somebody,” and “It’s a Great Day to Be Alive.” The Marietta, Georgia native built a successful career blending Southern rock and country. He is also credited with reuniting the Eagles in 1993 by inviting them for the video shoot of his cover “Take It Easy,” featured on the CMA Album of the Year Common Thread: The Songs of the Eagles. — D.E.P.
84. Patty Loveless
Patty Loveless performs on stage at the Country Music Festival held at Wembley Arena in April 1987 in London
Starting her musical journey at 12 with her brother Roger as the Singing Swinging Rameys in 1969, Patty Ramey (later Loveless) worked diligently for years before signing with MCA Records. Her breakthrough came with the 1988 album If My Heart Had Windows, featuring Hot Country Songs hits like Steve Earle’s “A Little Bit in Love” and the George Jones title track. Renowned as a premier song interpreter, Loveless achieved 20 top 10 hits, including heartbreaking ballads like “How Can I Help You Say Goodbye” and upbeat numbers like “I Think About Elvis.” Later, she revisited her Appalachian roots, winning a Grammy for 2009’s Mountain Soul II. – S.K.
83. DeFord Bailey
Widely recognized as the first Black country music star, DeFord Bailey broke barriers as the first African-American performer on the Grand Ole Opry. An exceptionally talented harmonica player, Bailey recorded significant tracks, including 1927’s “Pan American Blues,” one of the earliest recordings of a harmonica blues solo. His virtuosity made him an early pioneer in challenging racial boundaries in music. Although much of his career preceded major music institutions, Bailey’s profound impact, both in and out of the recording studio, continues to inspire generations of country music artists. — K.D.
82. Faith Hill
Faith Hill emerged in the early ‘90s with two chart-topping singles, “Wild One” and her spirited cover of Janis Joplin’s “Piece of My Heart,” from her triple-platinum debut Take Me as I Am (1993). Combining wholesomeness with allure and a captivating, throaty voice, Hill achieved massive crossover success. Hits like the timeless “This Kiss,” the Oscar-nominated “There You’ll Be,” and her Billboard 200 No. 1 album Breathe solidified her superstardom. Her record-breaking Soul2Soul tours with husband Tim McGraw further cemented her status as one of the most popular country singers of her era. — K.D.
81. Ernest Tubb
An avid fan of Jimmie Rodgers, the Crisp, Texas native Ernest Tubb led the Texas Troubadours and found success in 1941 with his breakthrough single, “Walking the Floor Over You,” characterized by its lovelorn theme and jaunty rhythm. His distinct honky-tonk style and straightforward, slightly off-pitch vocals (a result of a tonsillectomy) became his signature. Tubb was also known for his kindness to emerging artists like Johnny Cash, Loretta Lynn, and Elvis Presley, inviting them to perform on his Midnite Jamboree radio show. Launched in 1947, the show still airs weekly on Nashville’s WSM radio. – CHRISTINE WERTHMAN
80. Roy Clark
Alt: Popular country artist and Hee Haw host Roy Clark smiling warmly, holding his guitar in a classic portrait.
A prolific country artist in the ’60s, known for hits like 1963’s “The Tips of My Fingers,” Roy Clark truly cemented his legacy starting in 1969. That year, he became the co-host (with Buck Owens) of Hee Haw, the long-running TV variety show featuring country comedy and music. Reaching tens of millions of viewers, Hee Haw brought country music to a massive audience and boosted Clark’s own recording career; he scored eight Hot Country Songs top 10 hits between 1969 and 1976. The amiable multi-instrumentalist, particularly famed for his lightning-fast guitar skills, hosted the show until it ended in 1993. — ERIC RENNER BROWN
79. Morgan Wallen
In the 2020s, East Tennessee native Morgan Wallen sparked a wave of country music popularity reminiscent of Garth Brooks three decades prior. Wallen’s songs, often co-written by him, explore familiar country themes of liquor and heartbreak, but his music distinctively blends elements of hip-hop, pop, and alternative rock, delivered with his signature twangy vocals. His dominance is undeniable: on Billboard’s 2023 year-end charts, “Last Night” topped the Hot 100, and One Thing at a Time led the Billboard 200, making him the first male artist since Usher in 2004 to achieve both honors in the same year, solidifying his place among today’s most popular country singers. — M.N.
78. Eddy Arnold
Known as the “Tennessee Plowboy” due to his farming roots in Henderson, Tenn., Eddy Arnold first appeared on the Grand Ole Opry in 1943. Signing with RCA Victor the following year, he began a streak of hits including “The Cattle Call,” “What’s He Doing in My World,” and “Make the World Go Away.” Arnold’s use of lush orchestration and pop-influenced arrangements broadened his appeal beyond traditional country audiences, significantly contributing to the development of The Nashville Sound. In 1966, he became the youngest person inducted into the Country Music Hall of Fame at that time. — D.E.P
77. Barbara Mandrell
In 1981, Barbara Mandrell’s vibrant personality and versatile vocal talent led her to become the first artist to win the CMA Entertainer of the Year award twice consecutively. At the time, she and her sisters, Louise and Irlene, were starring in their successful NBC variety show, Barbara Mandrell and the Mandrell Sisters. Mandrell achieved six No. 1 hits on Hot Country Songs, including the upbeat “Sleeping Single in a Double Bed” and the classic “I Was Country When Country Wasn’t Cool” (featuring George Jones). A gifted singer, multi-instrumentalist, and performer, Mandrell retired in 1997 and was inducted into the Country Music Hall of Fame in 2009. – PAUL GREIN
76. Don Williams
Don Williams photographed in 1989.
With a soothing baritone that epitomized country music comfort, Don Williams enjoyed a prolific chart run from 1974 to 1991, achieving 17 No. 1 Hot Country Songs hits, including “Heartbeat in the Darkness,” “Lord, I Hope This Day Is Good,” and “Tulsa Time.” The Floydada, Texas-born singer, songwriter, and guitarist, who passed away in 2017, started in the folk trio Pozo-Seco Singers before connecting with Jack Clement in Nashville, who recognized Williams’ unique talent for delivering his own songs. Known as “The Gentle Giant” for his understated style, Williams saw his songs widely covered, but none captured the essence of lines like “I’m not saying I’m a righteous man/ But Lord I hope you understand” quite like he did. — S.K.
75. Freddy Fender
Mexican-American singer-songwriter Baldemar G. Huerta adopted the stage name Freddy Fender when transitioning from conjunto to rockabilly in the 1950s. His career soared in 1975 with the massive crossover hit “Before The Next Teardrop Falls,” which topped both the Hot Country Singles chart and the Hot 100. The song, featuring a verse in Spanish, won the CMA Award for Single of the Year. In 1975, he also topped the country chart with “Wasted Days and Wasted Nights” and “Secret Love,” followed by “You’ll Lose a Good Thing” in 1976. In the 1990s, he earned Grammys with the Tex-Mex supergroups The Texas Tornados and Los Super Seven. Fender passed away in 2006. — J.N.
74. Martina McBride
Blessed with a powerful and angelic voice, Martina McBride brought lilting strength to every song, showcasing her impressive range and dynamic delivery. Despite often pop-leaning productions, McBride didn’t shy away from sensitive topics during her peak chart run in the ’90s and ’00s (which included five Country Airplay No. 1s, like the five-week chart-topper “I Love You” in 1999). This was particularly evident in “Independence Day,” her bold anthem celebrating freedom for survivors of domestic violence, making her a significant voice among female country singers. – KATIE ATKINSON
73. Blake Shelton
Blake Shelton’s legacy encompasses more than just his impressive country music stats—74 Hot Country Song entries, seven No. 1 Top Country Albums, and 10 CMA Awards. His musical reach extends further, covering rock classics by Tom Petty and Aerosmith, and recently embracing country-pop with Post Malone on “Pour Me a Drink.” Simultaneously, his long tenure as an original coach on The Voice (2011-2023) and his high-profile relationship with wife Gwen Stefani (with whom he’s recorded and performed) have solidified Shelton’s position as a mainstream ambassador for country music, keeping him firmly among the most popular country singers today. — LYNDSEY HAVENS
72. Trisha Yearwood
Alt: Popular female country singer Trisha Yearwood smiling warmly at an industry event, celebrated for her powerful voice.
Inspired by musical heroes like Linda Ronstadt, Trisha Yearwood possesses a powerhouse voice whose range and nuance establish her as one of the most revered female vocalists of recent decades. She consistently impresses with her song selection and delivery, captivating a broad audience with a seamless fusion of country, folk, and pop vocals. This blend is evident in enduring classics like “She’s in Love With the Boy” and “How Do I Live.” Yearwood has earned three Grammys and three CMA Awards, including Female Vocalist of the Year in 1997 and 1998. — RYLEE JOHNSTON
71. Keith Urban
Though raised in Australia, Keith Urban is now claimed by Nashville, having evolved into one of country music’s most dynamic shapeshifters. He masterfully blends various styles while keeping country as his foundation. His fluid guitar playing has made the CMA Entertainer of the Year (2005, 2018) one of the genre’s premier guitarists and a global live draw. Upbeat anthems like “Somebody Like You,” “Wasted Time,” and “Days Go By” are perfect for open-road listening, while sultry tracks like “Making Memories of Us,” “You Look Good In My Shirt,” and “Blue Ain’t Your Color” ignite romance, showcasing his versatility and enduring popularity. – M.N.
70. Brenda Lee
The resurgence of Brenda Lee’s classic “Rockin’ Around the Christmas Tree” to No. 1 on the Billboard Hot 100 in December 2023—65 years after its release—marked a late-career triumph for the then-79-year-old Atlanta native, making her the oldest artist to top the chart. However, the success of this holiday staple sometimes overshadows Lee’s seven decades of vocal artistry. Her voice could quiver, growl, break, or soar, adapting perfectly to the lyric. Often backed by lush countrypolitan arrangements, Lee became one of country music’s most important early crossover artists, scoring Hot 100 No. 1s like “I’m Sorry” (at age 15) and “I Want to Be Wanted,” alongside top ten hits “Emotions” and “Break It To Me Gently.” — THOM DUFFY
69. Clint Black
Alongside Garth Brooks and Alan Jackson, Clint Black was a central figure in the late ’80s surge of “hat acts” that propelled country music to new popular heights. With his blend of traditional country, Western swing, and honky-tonk, Black achieved remarkable dominance, securing the No. 1 Billboard Year-End Country Song in both 1989 (“A Better Man”) and 1990 (“Nobody’s Home”)—a feat not seen in 35 years. In 2024, Black celebrated the 35th anniversary of Killin’ Time, touring the classic album which spent an impressive 31 weeks atop the Country Albums chart, reaffirming his status as one of the era’s most popular country singers. — K.D.
68. Statler Brothers
This Virginia quartet—brothers Harold and Don Reid, Phil Balsley, and Lew DeWitt—rose to prominence with their gospel-influenced harmonies and captivating concerts. Starting in 1964, they spent eight years touring with Johnny Cash and scored a No. 2 Country Songs hit (and top 5 Hot 100 hit) with DeWitt’s composition “Flowers on the Wall.” They followed with country top 10s like “Bed of Rose’s,” “The Class of ‘57,” and the No. 1 hit “Do You Know You Are My Sunshine.” After DeWitt left due to health issues in 1982, Jimmy Fortune joined, and the group achieved three more chart-toppers penned by Fortune: “Elizabeth,” “My Only Love,” and “Too Much on My Heart.” The Statler Brothers won nine CMA Vocal Group of the Year awards and hosted a popular TNN variety show in the 1990s. — J.N.
67. Linda Martell
Linda Martell poses for a portrait circa 1969 in Nashville, Tennessee.
The term “pioneer” truly applies to Linda Martell, who, in 1969, became the first Black woman to perform on the Grand Ole Opry. Her breakthrough single, the sweet “Color Him Father,” reached No. 22 on the Hot Country Songs chart in September 1969. It remained the highest-charting single by a Black woman on that chart for over 50 years, until Beyoncé’s “Texas Hold ’Em” hit No. 1 in February 2024. Martell left Nashville in 1974 due to industry challenges but reemerged significantly on two tracks of Beyoncé’s Cowboy Carter, earning her first Grammy nomination in 2024 for her contribution to “SPAGHETTII.” – M.N.
66. Jerry Reed
One of country’s great storytellers and hitmakers of the ’70s, Jerry Reed gained prominence early in the decade with lively story songs like “Amos Moses” and “When You’re Hot You’re Hot.” His charismatic Southern delivery and talent for catchy hooks even propelled him into the top 10 of the Billboard Hot 100. Later, his song “Eastbound and Down” achieved pop culture immortality through its feature in the blockbuster Smokey and the Bandit. In the ’80s, Reed enjoyed a resurgence with humorous country hits “The Bird” and “She Got the Goldmine (I Got the Shaft).” – ANDREW UNTERBERGER
65. Toby Keith
Years before his defiant 2002 hit “Courtesy of the Red, White and Blue (The Angry American),” Toby Keith topped the Hot Country Songs chart in 1993 with his debut single, the nostalgic “Should’ve Been a Cowboy.” The son of a veteran, Keith often wore his patriotism proudly. His powerful baritone voice was equally suited to more playful tracks, like the Willie Nelson duet “Beer for My Horses” (a six-week No. 1) and the cleverly knowing “As Good As I Once Was.” His consistent chart success and strong persona made him one of the most popular country singers for decades. — C.W.
64. Ronnie Milsap
With a voice as smooth as butter, Ronnie Milsap was instrumental in establishing lush, emotionally open country music as a major commercial force in the ‘70s and ‘80s. A master pianist despite being mostly blind since birth, Milsap crafted a warm, reassuring sound that drew from diverse influences like doo-wop and soul. His music often explored themes of heartbreak, longing, and devotion, resonating widely. This crossover appeal led to an incredible 35 No. 1 hits on the Hot Country Songs chart between 1974 and 1989, cementing his place among country music legends. – JOE LYNCH
63. Ray Price
The artistically versatile Ray Price helped reshape country music multiple times. In the 1950s, songs like his 20-week No. 1 country hit “Crazy Arms” introduced a dynamic honky-tonk style known as the “Texas shuffle,” featuring a 4/4 rhythm and walking bass line. In the 1960s, he shifted gears again, embracing lush string arrangements and a smooth vocal style associated with “The Nashville Sound,” exemplified by his versions of “Danny Boy” and Kris Kristofferson’s “For the Good Times.” Price also championed rising talents, recording Harlan Howard’s “Heartaches By the Number” and Bill Anderson’s “City Lights.” His band notably included future stars Willie Nelson, Roger Miller, and Johnny Paycheck. Price was inducted into the Country Music Hall of Fame in 1996. — J.N.
62. Kitty Wells
Hank Thompson’s 1952 hit “The Wild Side of Life” criticized a woman for enjoying nightlife, deeming her unfit for marriage. This inspired one of country music’s most powerful responses: Kitty Wells’ chart-topping debut single, “It Wasn’t God Who Made Honky Tonk Angels.” This song paved the way for female empowerment and revenge themes in country music, influencing artists from Tammy Wynette to Carrie Underwood. Wells became a trailblazer for generations of successful women country stars. Despite her career launching with a song about infidelity, Wells was married to country singer Johnny Wright for nearly 75 years until his death in 2011. Wells passed away the following year at 92. — T.D.
61. Jerry Lee Lewis
While “The Killer” was a rock ‘n’ roll pioneer with Sun Records’ Class of ’55, Jerry Lee Lewis grew up in Louisiana with country roots. His first performance was actually with a country & western band. His defiant, high-energy piano style (and tumultuous personal life) made him an outlaw figure before the term became common in country music. He achieved 30 Top 10 hits in the genre, including a No. 1 cover of Kris Kristofferson’s “Me and Bobby McGee.” Lewis is honored in multiple halls of fame, including Country, Rock and Roll, Rockabilly, and Memphis Music. – G.G.
60. Roger Miller
Alt: Famous country singer and songwriter Roger Miller, “King of the Road,” in a thoughtful portrait during the 1960s.
Roger Miller, the star behind the 1960s massive hit “King of the Road,” famously sang, “I’m a man of means, by no means.” After serving in the Army during the Korean War, Miller worked various jobs—bellhop, fireman—while writing and pitching songs in Nashville and Amarillo. By 1958, his songs were being recorded by stars like George Jones and Ernest Tubb. His own breakthrough came in 1964 with the quirky smash “Dang Me,” followed by hits like “Chug-a-Lug” and “Do-Wacka-Do,” establishing his unique, comedic style. In 1985, Miller became the first country songwriter to win a Tony Award for Best Original Score for the Broadway musical Big River. He passed away in 1992. – S.K.
59. The Louvin Brothers
Rooted in country gospel and known for their haunting close harmonies, the Louvin Brothers were a quintessential “brother act.” They bridged the gap between earlier old-time duos like the Delmore Brothers and modern acts like the Everly Brothers. Active in the ‘50s and ‘60s, they became a key influence on alternative country after the Byrds covered their song “The Christian Life” on Sweetheart of the Rodeo. Their legacy was amplified by their contrasting personas: Ira Louvin possessed an angelic high tenor but was known for his volatile behavior, embodying country music’s classic tension between Saturday night revelry and Sunday morning repentance. – ROB LEVINE
58. Charlie Rich
With a resonant vocal style more aligned with Elvis Presley’s pop balladry than Hank Williams’ honky-tonk, Charlie Rich became a defining “countrypolitan” singer of the ‘70s. His recordings, often featuring slick orchestrations and polished backing vocals (frequently guided by producer Billy Sherrill), targeted a crossover audience with themes of heartbreak, devotion, and loneliness. Rich earned nine No. 1 hits on the Hot Country Songs chart, including his signature smash, “The Most Beautiful Girl,” which also topped the Hot 100 in 1973. Despite the polished sound, the “Silver Fox’s” effortless and skillful delivery ensured his authenticity was never in doubt. – J.L.
57. Hank Williams Jr.
Hank Williams Jr. faced the immense challenge of following his legendary father’s footsteps. After initially performing as a Hank Williams impersonator, a life-altering mountain climbing accident spurred him to forge his own path. He emerged in the late ‘70s and ‘80s as a country-rock outlaw, successfully upholding his “Family Tradition.” Nicknamed Bocephus by his father, he became synonymous with rock-infused outlaw country, delivering hits like “All My Rowdy Friends Are Coming Over Tonight,” “Whiskey Bent and Hell Bound,” and “Born to Boogie.” His iconic Monday Night Football theme earned him four Emmy Awards, and he was eventually inducted into the Country Music Hall of Fame, proving his own unique popularity and influence. — D.E.P.
56. Eric Church
Known for his rebellious attitude, potent songwriting, and innovative sound, Eric Church has consistently pushed country music boundaries since his early 2000s debut. He blends country with rock, blues, and folk while remaining connected to the genre’s roots. Church’s impact stems from his bold artistic choices and commitment to creative integrity. He crafts albums like Chief and The Outsiders that often defy commercial trends, appealing to both traditional country fans and new listeners. His live shows are legendary—often hours long, unscripted, and fueled by raw energy, spontaneity, and a powerful connection with his devoted fanbase, “the Church Choir.” – DAVE BROOKS
55. Linda Ronstadt
Linda Ronstadt portrait 1973
Though primarily known for her interpretations of others’ songs, Linda Ronstadt possessed a singular voice—described by producer John Boylan as “big as a house”—that expertly navigated the line between pop and country. She made even well-known hits like Roy Orbison’s “Blue Bayou” and the Everly Brothers’ “When Will I Be Loved” distinctly her own. Ronstadt achieved her only Hot 100 No. 1 in 1975 with a powerful rendition of “You’re No Good.” Modern audiences might recognize her best for her heartbreaking 1970 solo breakthrough, “Long, Long Time,” which experienced a chart resurgence in 2023 after its memorable feature in HBO’s The Last of Us. – A.U.
54. Luke Combs
After leaving Appalachian State University, Luke Combs drove to Nashville and worked his way up from small bars to larger venues, performing songs like “Hurricane.” Delivered in Combs’ resonant baritone, “Hurricane” became the first of his remarkable 13 consecutive Country Airplay No. 1 hits. Whether singing about broken hearts or beer, he quickly established himself as one of country music’s most reliable and most popular country singers. His 2023 cover of Tracy Chapman’s 1988 classic “Fast Car” reached No. 2 on the Hot 100 and led to a memorable Grammy Awards duet with Chapman. A two-time CMA Entertainer of the Year, Combs now regularly headlines stadiums. – S.K.
53. Brad Paisley
Brad Paisley consistently captivates fans, whether through his exceptional, fluid guitar playing or his clever lyrical wordplay. He can evoke laughter with songs like “I’m Gonna Miss Her,” “Ticks,” and “Celebrity,” then move listeners to tears with tunes like “Whiskey Lullaby” (featuring Alison Krauss) or “I’ve Been Better.” Paisley also encourages reflection with songs that explore themes beyond country’s traditional scope, such as “Welcome to the Future,” “American Saturday Night,” and “Southern Comfort Zone.” In 2008, the West Virginia native became the first artist to achieve 10 consecutive Country Airplay No. 1 hits. The 2010 CMA Entertainer of the Year now boasts 24 non-consecutive No. 1s on the chart. – M.N.
52. Tim McGraw
Since his 1994 breakthrough with “Indian Outlaw,” Tim McGraw has enjoyed an enduring 30-year career at the forefront of country music and beyond. His achievements include 39 Country Airplay No. 1s among 60 top 10 hits, massive tours (solo and with wife Faith Hill), and a consistent ability to deliver both heartfelt ballads and energetic party anthems. McGraw has remained relevant by embracing evolving sounds, from his top five Hot 100 hip-hop collaboration with Nelly (“Over and Over,” 2004) to joining Post Malone’s recent country album (“Wrong Ones”). His influence is undeniable—Taylor Swift even named her debut single after him, highlighting his status as one of the most popular country singers of his generation. – K.A.
51. Charlie Daniels
Alt: Country rock legend Charlie Daniels holding his fiddle in a classic black and white portrait.
Though famed for iconic country rock anthems like “The South’s Gonna Do It Again,” “In America,” and “The Devil Went Down to Georgia,” Charlie Daniels’ career was far more extensive than his radio hits suggest. The North Carolina native was a versatile multi-instrumentalist who became an in-demand Nashville session player, contributing to albums like Bob Dylan’s Nashville Skyline and Ringo Starr’s Beaucoups of Blues. In 1974, Daniels launched his annual Volunteer Jam concert series, uniting diverse artists such as Amy Grant, Lynyrd Skynyrd, and Stevie Ray Vaughan. The Country Music Hall of Famer, who passed away in 2020, also recorded gospel, blues, and bluegrass albums and was a best-selling author. – D.E.P.
50. Tanya Tucker
A Texas-born firebrand with a powerful voice, Tanya Tucker began her career as a teenage sensation, gracing the cover of Rolling Stone at 15. She scored her signature hit, “Delta Dawn,” in 1972, followed by successes like “Love’s the Answer” and “What’s Your Mama’s Name,” leading to a $1.4 million record deal. After an ’80s comeback and relentless touring, a remarkable resurgence occurred in 2019 through collaborations with Brandi Carlile and Shooter Jennings. This culminated in 2020 Grammy wins for Best Country Song and Best Country Album, reaffirming her enduring talent and popularity. — S.K.
49. Kenny Chesney
A dominant force in both touring and chart performance, Kenny Chesney’s career is marked by significant milestones. He surpassed $1 billion in career gross from live shows and achieved his 33rd Country Airplay No. 1 this summer with “Take Her Home.” Chesney successfully translated his laid-back “No Shoes, No Shirt, No Problems” ethos into a lifestyle brand, inspiring his dedicated “No Shoes Nation” fanbase and ensuring his carefree country sound remains authentic. This strategy has proven highly effective for the star, who boasts 98 total entries on both Country Airplay and Hot Country Songs charts and has won the CMA Entertainer of the Year award four times, second only to Garth Brooks in that category. – L.H.
48. Marty Robbins
Country music’s deep connection to NASCAR is exemplified by Marty Robbins. The hitmaker, who scored the first of his 17 No. 1 Country Songs hits with “I’ll Go On Alone” in 1952, was an avid racing fan who became a driver in the early ’70s, achieving six top 10 finishes. A race was established in his name a year after his death in 1982. Robbins released 52 studio albums and over 100 singles, including 1957’s “A White Sport Coat” and his most famous song, the haunting 1959 murder ballad “El Paso,” which was his only crossover No. 1 on the Billboard Hot 100. — G.G.
47. Conway Twitty
Conway Twitty portrait from the 1960s
Although his career began with the Elvis Presley-influenced Hot 100 No. 1 hit “It’s Only Make Believe” in 1958, Conway Twitty transitioned from rock ‘n’ roll hopeful to a country music superstar. Over 25 years, the pompadoured singer topped the Hot Country Songs chart an astonishing 40 times. Whether performing solo or with frequent duet partner Loretta Lynn, Twitty favored a direct, twangy sound (often featuring steel guitar legend John Hughey) while delivering subtly mature songs exploring themes of sex, infidelity, and guilt, making him one of the most popular country singers of his era. – J.L.
46. Brooks & Dunn
The powerhouse duo of Kix Brooks and Ronnie Dunn, initially paired by their label head in 1990, revitalized traditional country with hits like “Boot Scootin’ Boogie” and “My Maria.” Their music helped revive line dancing and significantly fueled the country music boom of the ‘90s. They combined Brooks’ gritty vocal tone with Dunn’s powerful, emotive voice and strong songwriting, creating a signature sound that blended rock, blues, and classic country elements. Brooks & Dunn’s widespread impact is highlighted by their record-tying 18 CMA Awards as a duo (matched only by Vince Gill), solidifying their status as hugely popular figures in country music history. — D.B.
45. The Oak Ridge Boys
Even if the Oak Ridge Boys had only given the world the irresistible sing-along anthem “Elvira” in 1981, their contribution would be significant. However, this premier country vocal group offered much more. Originating in the ‘40s as a Southern gospel group, they transitioned to country music in the mid-‘70s, incorporating doo-wop influences and rich, layered harmonies that captivated audiences. The quartet, which continues touring even after the passing of tenor Joe Bonsall in July 2024, has achieved 34 Top 10 hits on the country charts, proving their enduring popularity across decades. – M.N.
44. Porter Wagoner
Inducted into the Country Music Hall of Fame in 2002, Porter Wagoner left an indelible mark on country music. He was a style icon, famous for his dazzling Nudie and Manuel suits, and a successful hitmaker with songs like “The Carroll County Accident,” “A Satisfied Mind,” and “Misery Loves Company.” Perhaps most significantly, he introduced Dolly Parton to the world, hiring her in 1967 for his popular television program, The Porter Wagoner Show. Parton’s timeless classic “I Will Always Love You” was written about ending her professional partnership with Wagoner. Before his passing in 2007 at age 80, Wagoner charted 81 singles and entertained millions for decades as a Grand Ole Opry stalwart. –- D.E.P.
43. Bob Wills
Dubbed the King of Western Swing, Bob Wills was a pivotal figure who laid much of the groundwork for modern country music. Author of classics like “San Antonio Rose” and “Take Me Back to Tulsa,” and leader of the Texas Playboys, this 1930s star initially struggled, working various jobs from construction to preaching while moonlighting with his pioneering blend of hillbilly and jazz music at local dances and shows. His band, which at one point included Merle Haggard, eventually broke through on Tulsa radio. Wills became a prolific and ultimately legendary recording artist, profoundly shaping the sound of country music. — S.K.
42. Roy Acuff
Country music transformed with the arrival of Tennessee-born Roy Acuff. Known as the King of Country Music, Acuff shifted the genre’s focus from primarily instrumental to vocal-centric with 1940s hits like “The Prodigal Son,” “Our Own (Jole Blon),” and “Blue Eyes Crying in the Rain.” The fiddle-playing singer made an even greater contribution by co-founding Acuff-Rose Music, one of Nashville’s earliest and most influential publishing houses, with songwriter Fred Rose. They championed artists like Willie Nelson, Lefty Frizzell, and Roy Orbison. In 1962, Acuff became the first living artist inducted into the Country Music Hall of Fame. — G.G.
41. Taylor Swift
Alt: Global superstar Taylor Swift performing during her early country music era on the Fearless Tour in 2009.
As Taylor Swift dominates the global pop stage with the biggest tour ever, it’s easy to forget the immense impact of her early country music career. Across four classic albums released in just six years, the young singer-songwriter revolutionized the genre with catchy hooks and deeply personal lyrics, earning seven Country Airplay No. 1s among 18 top 10 hits. Swift tapped into country’s rich storytelling tradition, seemingly writing songs straight from her diary. While grounded in tradition, she blazed a unique trail as a teenage female songwriter, attracting a massive new fanbase that has only grown exponentially since. Though now a global phenomenon, her journey to becoming one of the world’s most popular singers began in Nashville. – K.A.
40. The Everly Brothers
Inducted into both the Rock and Roll Hall of Fame (in its inaugural 1986 class) and the Country Music Hall of Fame, Tennessee brothers Phil and Don Everly were pioneers of country-rock in the late ’50s and ’60s. From the start, the Everlys and their exquisite harmonies existed at the crossroads of country and rock. Early supporters included Nashville legends Chet Atkins and Wesley Rose, while their early tours included rock icon Buddy Holly. This unique blend resulted in a phenomenal chart run after their 1956 debut, launching numerous songs to the top of the country charts, including “Bye Bye Love,” “Wake Up Little Susie,” and “All I Have to Do is Dream.” The Everly Brothers remain influential; in 2013, Norah Jones and Green Day’s Billie Joe Armstrong released Foreverly, a tribute album covering their songs. — E.R.B.
39. Gene Autry
Gene Autry, “The Singing Cowboy,” earned his nickname authentically. Raised on an Oklahoma ranch and a competitor in rodeos, he channeled that Western experience into his signature croon on iconic standards like “Back in the Saddle Again.” Autry’s extensive Christmas recordings also made him a beloved voice of the holiday season. He became a true multimedia mogul, holding the unique distinction of being the only person awarded stars in all five categories (music, film, television, radio, live performance) on the Hollywood Walk of Fame. Additionally, he was the longtime owner of Major League Baseball’s California/Anaheim Angels. — G.G.
38. Dwight Yoakam
Though now highly revered, Dwight Yoakam initially faced rejection in Nashville. Fortunately, this led him to Los Angeles, where he performed opening slots for punk and rock bands, forging his unique “cowpunk” style and cementing his impact on the genre. While his first three albums topped the Top Country Albums chart, it was his fifth album, 1993’s This Time, that solidified his superstardom. Its lead single, “Ain’t That Lonely Yet,” earned Yoakam the first of his two Grammys. Another standout track, “A Thousand Miles from Nowhere,” became the first of many instances he would perform with his now-close friend and admirer, Post Malone, starting with a live duet on Yoakam’s SiriusXM channel in 2018. – L.H.
37. Emmylou Harris
With her distinctively textured vocals and exceptional song selection, Emmylou Harris has built a career as a transcendent and highly influential voice in country music, marked by remarkable versatility. After working in the East Coast folk scene, she gained prominence backing Gram Parsons. In the 1970s and 1980s, Harris emerged as a leading artist, achieving seven Hot Country Songs chart-toppers, including the Earl Thomas Conley duet “We Believe in Happy Endings” and covers of Buck Owens’s “Together Again” and Patsy Cline’s “Sweet Dreams.” She also mentored rising talent, with her bands featuring future stars like Rodney Crowell, Ricky Skaggs, and Buddy Miller. Additionally, Harris collaborated with Dolly Parton and Linda Ronstadt on the essential Trio albums (1987, 1999). — J.N.
36. Elvis Presley
Elvis Presley Performing in 1956
Widely known as the “King of Rock and Roll,” Elvis Presley’s early career was deeply influenced by country, gospel, and blues. His initial recordings at Sam Phillips’ Sun Records, particularly “Blue Moon of Kentucky,” were groundbreaking in fusing traditional country with the upbeat, rhythmic energy of rockabilly. This hybrid sound, infused with Presley’s unique Americana style, introduced country music to broader audiences and established him as one of the first major crossover artists. His electrifying televised performances brought unprecedented (and often controversial) energy to country music, profoundly influencing legends like Johnny Cash, Dolly Parton, and Willie Nelson, making him undeniably one of the most popular singers across genres. – D.B.
35. Carrie Underwood
The best-selling artist to emerge from American Idol, the 2005 winner Carrie Underwood is also one of country music’s most vocally gifted performers. Her 2007 revenge anthem “Before He Cheats” spent over a year on the Hot 100, but her primary impact has been on the country charts. Eight of her nine studio albums debuted at No. 1 on Top Country Albums, and she has scored 16 No. 1 singles on Country Airplay. Underwood leads all Idol alumni with eight Grammy wins and is the only woman to win the ACM Entertainer of the Year award three times. Her powerful voice allows her to hold her own alongside rock legends like Axl Rose and Steven Tyler, securing her place among the most popular country singers of the modern era. — R.J.
34. Miranda Lambert
For nearly 25 years, Miranda Lambert has provided the soundtrack for a generation of country music enthusiasts. Hailing from Longview, Texas, the three-time Grammy-winning vocalist, songwriter, and guitarist has sent seven albums to the top of the Country Albums chart, including the all-genre Billboard 200 No. 1, Platinum (2014). From 2005’s fiery “Kerosene” to 2024’s relatable “Dammit Randy,” Lambert’s honest songwriting and heartfelt vocals define both her fierce anthems and introspective ballads. She also excels as an interpreter, delivering stunning renditions like the sentimental “The House That Built Me.” Holding the record for the most ACM Awards won by any artist, Lambert remains a leading figure in authentic, heartfelt country music. – K.D.
33. John Denver
Though Charlie Rich famously burned the envelope when John Denver was named Entertainer of the Year at the 1975 CMA Awards, Denver undoubtedly earned his country credentials. More than five decades after his solo debut and 27 years after his untimely death in 1997, Denver remains a significant artistic influence for countless contemporary stars across genres—Lana Del Rey, MGK, and Jelly Roll are among those who have recently paid tribute. Inspired by the natural splendor of his adopted home state, Colorado, the charming, bespectacled Denver penned iconic rural American anthems like “Rocky Mountain High” and “Take Me Home, Country Roads.” As he joyfully sang, “Thank God I’m a country boy.” – HANNAH DAILEY
32. Vince Gill
Vince Gill boasts numerous hits, including four Hot Country Songs No. 1s during his peak commercial period from 1992-94. However, his country superstardom has always centered on his distinctive voice. Whether delivering the sweet harmonies of “When I Call Your Name” or recalling meeting his wife Amy Grant in “Whenever You Come Around,” Gill’s plaintive, tender tenor infuses his songs with unparalleled emotional depth. He found a perfect way to continue sharing that voice globally by joining the Eagles in 2017, following the passing of founding member Glenn Frey, further showcasing his enduring talent and appeal. – K.A.
31. Buck Owens
Alt: Bakersfield Sound pioneer Buck Owens performing live on stage with his signature guitar in 1969.
While many remember Buck Owens for hosting Hee Haw from 1969-1986, his musical contributions outside the comedic variety show were far more groundbreaking. During the ’60s, when smoother sounds dominated country radio, Buck Owens & His Buckaroos (featuring guitarist Don Rich) brought a gritty honky-tonk energy and a danceable rock ‘n’ roll shuffle to the airwaves and stages, including a performance at Carnegie Hall in 1966. As a key figure of the “Bakersfield sound,” Owens topped the Hot Country Songs chart 21 times. He also broke new ground on the business side, becoming one of the first country artists to establish his own music publishing company and own multiple radio stations. — J.L.
30. Alison Krauss
A unique talent known for both her angelic voice and her exceptional fiddle playing, Alison Krauss began recording at age 14. Her career spans solo work, collaborations with her band Union Station, projects with rock legend Robert Plant (Led Zeppelin), and contributions to acclaimed soundtracks like O Brother, Where Art Thou? and Cold Mountain. The Illinois native has earned 27 Grammy Awards, ranking fourth among all artists in history. Krauss received a National Medal of the Arts in 2019 and was inducted into the International Bluegrass Hall of Fame in 2021, highlighting her immense contribution and popularity across genres. – G.G.
29. Chris Stapleton
Chris Stapleton’s raw, soulful voice—often compared more to legends like Johnny Cash than his contemporaries—made an immediate impact with the release of Traveller in 2015. His Americana-influenced style continued to resonate, landing over 30 songs on the Hot Country Songs chart, including chart-toppers “Tennessee Whiskey,” “You Should Probably Leave,” and “Starting Over.” With five studio albums, Stapleton has already amassed 10 Grammy Awards, 10 ACM Awards, and 14 CMA Awards. Named Artist-Songwriter of the Decade by the Academy of Country Music, his blend of Southern rock and blues has made him one of the most decorated and most popular country singers of the last decade. – T.M.
28. Bill Monroe
Throughout the 1940s, Bill Monroe transformed the old-time folk and country music he grew up with by adding distinct instrumentation and rhythms, earning him the title “Father of Bluegrass.” His signature “high lonesome sound,” characterized by harmony singing and intricate banjo breakdowns, profoundly shaped the sound and feel of country music. Various iterations of his band, the Blue Grass Boys, served as a training ground for top genre talents, including Carter Stanley, Peter Rowan, Lester Flatt, and Earl Scruggs. Monroe’s influence extended through the ’60s folk revival, impacting artists like Bob Dylan and Jerry Garcia, and continues to be felt today. – R.L.
27. Kris Kristofferson
Kris Kristofferson was a multifaceted talent: a singer, songwriter, Golden Globe-winning actor, and a foundational member of the supergroup The Highwaymen. Passing away in 2024, Kristofferson was also a Rhodes Scholar and former Army captain. His mastery of both melody and lyricism produced plain-spoken yet deeply evocative songs like “Why Me?,” “Me and Bobby McGee,” and “Sunday Mornin’ Comin’ Down” (written while he worked as a janitor in a Nashville studio). His nearly 60-year career, marked by countless covers of his songs, earned him induction into the Country Music Hall of Fame and a Grammy Lifetime Achievement Award, securing his legacy as one of country’s most respected figures. – G.G.
26. Glen Campbell
Glen Campbell Portrait Session 1967
In 1969, Glen Campbell’s By the Time I Get to Phoenix made history as the first country album to win the Grammy for Album of the Year. Possessing both a smooth, supple voice and exceptional guitar skills, Campbell achieved widespread success as both a musician and a celebrity, hosting his own popular variety show on CBS from 1969-1972. He was inducted into the Country Music Hall of Fame in 2005 and received a Lifetime Achievement Award from the Recording Academy in 2012. Even after an Alzheimer’s diagnosis, Campbell continued touring and recording, earning an Oscar nomination for co-writing “I’m Not Gonna Miss You” for the 2014 documentary Glen Campbell…I’ll Be Me. – P.G.
25. The Chicks
When The Chicks broke out in the late ’90s, the country music world hadn’t seen anything quite like them. Their sharp songwriting, heartfelt delivery, and expert musicianship led to multiple RIAA Diamond-certified albums (Wide Open Spaces, 1998; Fly, 1999) and massive hit singles like the fiery revenge story “Goodbye Earl” and the bluegrass-tinged singalong “Long Time Gone.” A political comment by frontwoman Natalie Maines in 2003 led to industry backlash, effectively ejecting them from Nashville’s mainstream. However, they returned triumphantly in 2006 with the brilliant, resilient album Taking the Long Way, reclaiming their narrative and winning the Grammy for Album of the Year, proving their enduring artistry and impact. – A.U.
24. Ray Charles
Alt: Music legend Ray Charles smiling during a television appearance, celebrated for bridging country and soul music.
Early decisions in the segregated record industry created a marketing divide between the working-class genres of country and blues. Ray Charles’s two volumes of Modern Sounds in Country and Western Music (1962) boldly challenged this separation. Applying rich big-band arrangements and lush strings to classic country songs like “I Can’t Stop Loving You” and “You Don’t Know Me,” Charles demonstrated the artistic depth of country music to a mainstream American audience. The immense pop success of Modern Sounds helped legitimize country music nationally and opened doors for greater Black participation in the genre, showcasing Charles’s unique ability to popularize diverse musical styles. — T.R.
23. Tammy Wynette
Often described as having “a tear in her voice,” Tammy Wynette possessed a soul-baring delivery capable of extracting every bit of emotion from a lyric. The Mississippi-born singer-songwriter masterfully conveyed heartbreak in ballads like “Another Lonely Song,” “’Til I Can Make it on My Own,” and “D-I-V-O-R-C-E,” while also delivering spirited, uptempo numbers like “Your Good Girl’s Gonna Go Bad” and “Singing My Song.” The Grammy-winning Country Music Hall of Famer recorded iconic duets with George Jones; their turbulent marriage often made headlines alongside their musical successes. Wynette also collaborated with artists like Dolly Parton, Loretta Lynn, David Houston, and even the British dance-pop group The KLF, whose 1991 track “Justified and Ancient” became a global hit. — D.E.P.
22. The Judds
The mother-daughter duo of the bluesy Wynonna and the harmonizing Naomi Judd dominated country music from 1984 to 1991. They achieved six multiplatinum studio albums and 14 No. 1 hits on the Country Songs chart, often characterized by polished, melancholic themes in songs like “Why Not Me,” “Mama He’s Crazy,” and “Girls’ Night Out.” Their journey began in a Kentucky mountain home, where Naomi raised Wynonna and future actress Ashley Judd on welfare after escaping an abusive relationship. In 1983, Naomi secured an RCA audition, launching their career. After Naomi’s hepatitis C diagnosis in the ’90s, she pursued writing and motivational speaking, with occasional Judds reunions. Following Naomi’s passing in 2022, Wynonna continues her successful solo career. — S.K.
21. Shania Twain
Shania Twain portrait from 1995
It’s impossible to discuss 1990s country music without highlighting Shania Twain, the undisputed Queen of Country Pop. The Canadian singer-songwriter captivated audiences worldwide with her sophomore album The Woman in Me (1995), which generated eight hit singles, including Hot Country Songs No. 1s “Any Man of Mine” and “(If You’re Not In It For Love) I’m Outta Here!” For over a decade, her stream of hits—including “Whose Bed Have Your Boots Been Under?,” “You’re Still the One,” “From This Moment On,” “That Don’t Impress Me Much,” and “Man! I Feel Like a Woman!”—seemed unstoppable, making countless pop fans fall in love with country music. Twain’s bold fusion of country vocals and pop production inspired future superstars like Taylor Swift, solidifying her status as one of the most popular country singers globally. — T.M.
20. Kenny Rogers
Kenny Rogers began his career in the late 1950s and achieved psych-rock success with The First Edition in the ’60s, but his fame truly skyrocketed when he fully embraced country music. His gravelly baritone provided instant authenticity to the storytelling songs he favored, most notably his signature hit, “The Gambler”—a song he embodied so well it felt autobiographical. After reaching No. 1 on the Hot 100 with the Lionel Richie-penned R&B crossover smash “Lady” in the ’80s, Rogers demonstrated his versatility again by topping the charts with his iconic country-pop duet with Dolly Parton, the Bee Gees-written “Islands in the Stream.” While comfortable exploring different genres, country music remained the core of this Texas native’s enduring appeal and easy swagger. — K.A.
19. Alan Jackson
In his post-9/11 anthem “Where Were You (When the World Stopped Turning),” Alan Jackson described himself as “just a singer of simple songs.” This ethos defines the reserved “songwriter’s songwriter,” even as a three-time CMA Entertainer of the Year with 26 Country Airplay No. 1s, most of which he penned himself. These “simple songs” are actually finely crafted depictions of small-town life, love, and heartbreak, encompassing enduring romance (“Home,” “Livin’ on Love”), family tributes (“Drive (For Daddy Gene)”), youthful fun (“Chattahoochee”), and sharp commentary (“Murder on Music Row,” “Gone Country”). As country music trended towards rock and hip-hop in the late ’90s and early 2000s, Jackson remained steadfastly country, continuing to score No. 1 hits and maintain his immense popularity. — J.N.
18. Keith Whitley
Alt: Influential traditional country singer Keith Whitley in a poignant black and white portrait.
During his tragically short life, Kentucky native Keith Whitley released only two solo albums, yet few artists have left such a lasting impact on country music. Starting his career in bluegrass legend Ralph Stanley’s band, Whitley moved to Nashville in 1983 and recorded a series of timeless hits, including “Miami, My Amy,” “When You Say Nothing at All,” “I’m No Stranger to the Rain,” and “Don’t Close Your Eyes.” Inducted into the Country Music Hall of Fame, the traditional vocalist passed away at 34 due to alcohol abuse, cutting short a promising career. Nevertheless, many contemporary artists still cite his profound influence, recognizing him as one of the genre’s most revered voices. — D.E.P.
17. Alabama
The band Alabama, hailing from Fort Payne, dominated country radio throughout the 1980s. Randy Owen, Teddy Gentry, Jeff Cook, and Mark Herndon delivered enduring hits like “Tennessee River,” “Love in the First Degree,” “Mountain Music,” “Dixieland Delight,” and “Feels So Right.” Owen’s evocative lead vocals combined with the group’s energetic stage presence earned them consecutive CMA Entertainer of the Year awards. The Academy of Country Music named Alabama Artist of the Decade for the ’80s. Beyond their musical achievements, the band’s greatest legacy might be the billion dollars raised through Country Cares for St. Jude Kids, an initiative Owen launched in 1989 to support St. Jude Children’s Research Hospital. — D.E.P.
16. Randy Travis
Randy Travis introduced a neo-traditionalist sound to country music in the 1980s, and audiences eagerly embraced it. His second album, Always and Forever, spent 43 weeks atop the Top Country Albums chart, a record at the time. Travis’s understated vocal twang and warm baritone perfectly suited classics such as “On the Other Hand” and “Forever and Ever, Amen.” He has won seven Grammys across country and gospel categories. Travis was inducted into the Country Music Hall of Fame in 2016, three years after suffering a debilitating stroke, cementing his legacy as one of the most popular country singers of his generation. – P.G.
15. The Carter Family
This Appalachian trio was truly a family enterprise: sisters Sara and Maybelle Dougherty married brothers A.P. Carter and Ezra Carter (the group’s manager). Responding to a newspaper advertisement, they became central figures in the 1927 Bristol Sessions, often called the “Big Bang of Country Music,” discovered alongside Jimmie Rodgers. Maybelle Carter’s innovative guitar picking (“Carter Scratch”) became a foundational technique for folk and country guitarists. The group’s exploration of themes like religion, family, and mortality contributed significantly to the melancholic tone often associated with early country music. The Carter Family left behind numerous standards, including “Keep on the Sunny Side” and “Will the Circle Be Unbroken,” and produced future legends like Maybelle’s daughter, June Carter Cash. — T.R.
14. Waylon Jennings
Starting his career in the late 1950s as bassist for fellow Texan Buddy Holly, Waylon Jennings brought his distinctive swagger and resonant voice to several hits in the 1960s (like “Only Daddy That’ll Walk the Line”). He achieved major stardom in the 1970s by joining Willie Nelson and others in challenging Nashville’s creative norms as part of the outlaw country movement. This decade saw Jennings score a string of No. 1 hits on Hot Country Songs, including the nostalgic “Luckenbach, Texas (Back to the Basics of Love)” and the iconic theme song for the popular TV series The Dukes of Hazzard. He also had successful duets with Nelson, such as “Good Hearted Woman” and “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” — T.D.
13. Jimmie Rodgers
Before earning the title “Father of Country Music,” a young Jimmie Rodgers followed his father’s path, working on the railroads in the 1910s and gaining the nickname “The Singing Brakeman.” By blending African American blues, mountain folk, vaudeville, and “hillbilly music,” Rodgers played a crucial role in establishing country music as a voice for working-class America. After the pivotal Bristol Sessions in 1927, Rodgers recorded “Blue Yodel No. 1 (T for Texas).” This early million-selling hit propelled country music into the national spotlight and sparked a nationwide yodeling phenomenon—his “blue yodels” became a viral sensation during the Great Depression, making him one of the first truly popular country singers. — J.L.
12. Patsy Cline
Patsy Cline portrait circa 1960
Patsy Cline was only 30 when she tragically died in a plane crash in 1963, yet her influence on music remains immeasurable. Her greatest hits, including “Walkin’ After Midnight,” “I Fall to Pieces,” and “Crazy,” are enduring classics. In 1973, she became the first solo female artist inducted into the Country Music Hall of Fame. The 1985 biopic Sweet Dreams, starring an Oscar-nominated Jessica Lange, introduced Cline to a new generation. In 1995, she received a Lifetime Achievement Award from the Recording Academy. Her album Patsy Cline’s Greatest Hits achieved RIAA Diamond certification in 2005, testament to her lasting popularity. — P.G.
11. Reba McEntire
Since her debut in the 1970s, Reba McEntire has become an undeniable force across country music and entertainment. Known for her emotive voice and signature multi-syllabic phrasing, she has charted over 100 songs on Hot Country Songs, including 24 No. 1 hits. McEntire built a reputation as a dynamic, multifaceted entertainer through elaborate concert tours featuring choreography and stunning costumes. Her music videos, like “Fancy” and “Is There Life Out There,” were cinematic and impactful. She further established herself as a versatile entertainer in television (Reba, The Voice), film (Tremors, North), and Broadway (Annie Get Your Gun). Winner of the CMA Entertainer of the Year award in 1986 and four Female Vocalist of the Year honors, McEntire joined the Country Music Hall of Fame in 2011, recognized as one of the most popular country singers and entertainers of all time. — J.N.
10. Merle Haggard
Alt: Outlaw country legend Merle Haggard performing live on stage during the 1980s.
A pivotal figure in the outlaw country movement of the ’70s, Merle Haggard wrote authentically from his experiences. As a young man, the California native spent time in correctional facilities, including San Quentin Prison, for various offenses. By the ’60s, Haggard was pursuing a career in country music, finding success as a key proponent of The Bakersfield Sound. However, as album titles like I’m A Lonesome Fugitive and The Legend of Bonnie & Clyde suggest, his outlaw spirit remained strong.
Haggard quickly became a commercial powerhouse with his proudly populist music, achieving an incredible 34 consecutive top 10 country hits between 1967 and 1977, ultimately scoring 38 country No. 1s between 1966 and 1987. Despite the controversial subject matter of his 1969 hit “Okie From Muskogee,” Haggard also became an unlikely countercultural icon, influencing artists from the Grateful Dead (who frequently covered his songs) to Willie Nelson (with whom he recorded four albums), solidifying his place as one of country music’s most complex and popular figures. — E.R.B.
9. George Strait
George Strait early portrait 1970s
George Strait, born in Poteet, Texas, has charmed audiences since his 1981 breakthrough album Strait Country with his incredibly smooth, subtly twangy voice. He skillfully delivers a curated mix of ballads, lively Western swing tunes, and traditional country two-steppers. Holding the record for the most No. 1 Country Songs hits by any artist, Strait achieved top 10 hits every single year for three decades (1990s-2010s), with classics like “Amarillo By Morning,” “The Fireman,” “You Look So Good in Love,” and “The Chair” captivating millions. His popularity remains immense; in 2024, he set an all-time U.S. attendance record for a ticketed concert, drawing 110,905 fans to Kyle Field at Texas A&M.
Strait remains country music’s most consistent performer, even down to his signature attire: pressed jeans, a button-down shirt, and a Stetson hat. He makes it all appear effortless, yet his dedication is clear in every meticulously crafted album. Known rightfully as the “King of Country,” George Strait continues his reign as one of the most popular country singers ever. — S.K.
8. Charley Pride
Alt: Trailblazing country music superstar Charley Pride in a portrait from the 1970s.
Charley Pride made history as country music’s first Black superstar. In 1971, he became the first (and remains the only) Black artist to win Entertainer of the Year at the CMA Awards. In 2000, he was the first Black artist inducted into the Country Music Hall of Fame. Known for his warm baritone and dignified presence, Pride approached his groundbreaking success with characteristic straightforwardness. “What came from my throat was my voice, no one else’s,” he wrote in his 1994 autobiography. “No one had ever told me that whites were supposed to sing one kind of music and Blacks another – I sang what I liked in the only voice I had.”
Pride achieved 29 No. 1 hits on Hot Country Songs and 12 No. 1 albums on Top Country Albums. He dominated the latter chart for 32 consecutive weeks in 1972 with back-to-back hit albums. Both featured his most memorable hit, “Kiss an Angel Good Mornin’,” a charming blend of politeness and desire. Pride received a Lifetime Achievement Award from the Recording Academy in 2017, three years before his passing, cementing his legacy as one of country music’s most beloved and popular figures. — P.G.
7. Garth Brooks
Garth Brooks leaning against a truck in 1992
Garth Brooks, a seven-time CMA Entertainer of the Year, propelled country music to unprecedented levels of popularity in the 1990s. Songs like “The Dance,” “Friends in Low Places,” “The Thunder Rolls,” and “Unanswered Prayers” became genre standards. Brooks combined down-to-earth charisma and a commitment to exceptional songwriting with electrifying, rock-influenced live shows that set a new standard for country concerts—featuring high-wire stunts and guitar smashing. He achieved multiple diamond-certified albums, including the game-changers No Fences and Ropin’ the Wind, making him the best-selling solo artist in U.S. history according to the RIAA.
In 1997, Brooks made history with a free concert in Central Park that drew an estimated one million people; the corresponding HBO special attracted 14.6 million viewers. At the peak of his fame, he surprised the industry by taking a long hiatus to raise his children. Returning after 13 years, the enduring power of his music and live performances was evident as his 2014-2017 World Tour sold over 6 million tickets, followed by his record-breaking Stadium Tour in 2019, reaffirming his status as arguably the most popular country singer of the modern era. – J.N.
6. George Jones
Alt: Legendary country singer George Jones in an early black and white portrait, known as one of the greatest voices in the genre.
Initially nicknamed “Possum” for his appearance and later “No Show Jones” for his occasional unreliability, George Jones ultimately earned the undisputed title as one of the greatest singers in country music history. His resonant baritone conveyed deep yearning, hardship, and heartache, echoing the genre’s most profound traditions. Listen to his 1962 No. 1 hit “She Thinks I Still Care,” where his voice cracks recalling “the same old places/ where the memory of her lingers everywhere.” Jones was a dominant force from 1955, when “Why Baby Why” became his first top 5 country hit. Even when chart hits waned, his devoted fanbase never did; he toured throughout his life.
Jones scored 13 No. 1 Country Songs hits, from the bootlegging narrative “White Lightning” (1959) to his cover of Merle Haggard’s “I Always Get Lucky With You” (1983). Three chart-toppers, including “Golden Ring” (1976), were duets with Tammy Wynette during their tumultuous marriage. However, Jones’s vocal masterpiece arrived in 1980 with “He Stopped Loving Her Today.” Penned by Bobby Braddock and Curly Putnam, it became his first No. 1 in six years, revitalized his career, and is widely considered the greatest country song ever written. Jones passed away in 2013. — T.D.
5. Hank Williams Sr.
Hank Williams portrait
In just 29 years, Hank Williams left behind a legacy of songs so achingly poignant they remain powerful decades later. From the raw desolation of “I’m So Lonesome I Could Cry” and the sharp accusation in “Your Cheatin’ Heart,” to the playful invitation of “Hey Good Lookin’” and the uplifting gospel standard “I Saw the Light,” Williams wrote and performed songs that reflected his own life while resonating deeply with millions. The Alabama native started his career in Montgomery in the 1930s, forming the Drifting Cowboys Band and leaving high school for music. Despite immense talent, struggles with alcohol and prescription drug addiction (due to chronic back pain) made him unreliable, leading to his dismissal from the Grand Ole Opry.
Williams died tragically on New Year’s Day 1953, in the back of a car en route to a performance in Ohio. Yet, his work continues to profoundly influence artists across generations, securing his place as one of the most seminal and enduringly popular figures in American music history. — D.E.P.
4. Loretta Lynn
Alt: Trailblazing female country singer Loretta Lynn in an early career portrait, known for her honest songwriting.
Despite her signature feminine style—often featuring frilly lace dresses and perfectly coiffed hair—Loretta Lynn was a powerful early advocate for women’s rights through her music. Songs like the controversial 1975 hit “The Pill,” addressing contraception, showcased her fearless approach. She refused to be overshadowed, famously warning off potential rivals in 1968’s “Fist City.”
Born in Butcher’s Hollow, Kentucky, Lynn cared for younger siblings before moving to Washington state, where she had four children by age 18. Her hitmaking career launched after performing on a Buck Owens-hosted TV show, starting with 1960’s “I’m a Honky Tonk Girl” (No. 14 on Country Songs). She went on to sell a reported 45 million albums, both solo and with longtime duet partner Conway Twitty (including their humorous hit, “You’re the Reason Our Kids Are Ugly”). Her autobiography, Coal Miner’s Daughter, inspired an iconic film starring Sissy Spacek. “You can call me your No. 1 you-know-what-kind of stirrer,” Lynn told Billboard in 2015. She passed away in 2022 at age 90, leaving behind a legacy as one of country music’s most influential and popular female country singers. — S.K.
3. Willie Nelson
Willie Nelson performing with American flag backdrop in 2002
Willie Nelson is more than a musician; he’s an American icon—hitmaker, outlaw, philanthropist, philosopher, actor, advocate for farmers and cannabis legalization. He has profoundly shaped country music and American culture since the early ‘60s, when he penned hits like “Crazy,” famously recorded by Patsy Cline. Unlike pioneers like Hank Williams whose careers burned brightly but briefly, Nelson has been a constant guiding star, shining steadily for decades.
Now 92, his musical legacy is vast, spanning from the landmark Outlaw album Red Headed Stranger (1975) and the multiplatinum standards collection Stardust (1978) to his recent release The Last Leaf on the Tree (reportedly his 153rd album). He has collaborated with an incredibly diverse range of artists, from Ray Charles (“Seven Spanish Angels”) and Julio Iglesias (“To All the Girls I’ve Loved Before”) to Snoop Dogg (“Roll Me Up and Smoke Me When I Die”). His advocacy for family farmers through the Farm Aid benefit concert, now in its 39th year, is the longest-running concert for a cause. Willie Nelson remains one of the most popular country singers and most beloved figures in American culture. — T.D.
2. Johnny Cash
Alt: The legendary “Man in Black,” Johnny Cash, performing live early in his career during the 1950s.
Known universally as “The Man in Black,” Johnny Cash was revered as a peerless vocalist and an artist whose music carried significant weight, often championing the marginalized and overlooked. Recording for Sun Records in the 1950s, Cash pioneered a sparse, driving rockabilly sound that connected with both pop and country audiences through hits like “I Walk the Line” and “Cry, Cry, Cry.” Moving to Columbia Records, he released his signature song “Ring of Fire” in 1963 and explored diverse themes through concept albums like Blood, Sweat and Tears, incorporating gospel, folk ballads, and protest songs into his repertoire.
The years 1968 and 1969 yielded his seminal live albums, At Folsom Prison and At San Quentin, producing timeless hits like “Folsom Prison Blues” and “A Boy Named Sue,” and earning him the CMA Entertainer of the Year award in 1969. His variety show, The Johnny Cash Show, featured influential artists like Bob Dylan. In the 1970s, he formed the supergroup The Highwaymen with Kris Kristofferson, Willie Nelson, and Waylon Jennings. Cash experienced a late-career renaissance in the 1990s with the stripped-down American Recordings series produced by Rick Rubin, notably receiving critical acclaim for his haunting cover of Nine Inch Nails’ “Hurt” in the early ’00s. Inducted into the Country Music Hall of Fame in 1980, Cash passed away in 2003, leaving an indelible legacy as one of the most popular country singers and influential artists of all time. — J.N.
1. Dolly Parton
Dolly Parton portrait from 1975
There has never been anyone quite like Dolly Parton, and it’s hard to imagine there ever will be again. She embodies an unparalleled mix of extraordinary talent, fierce determination, an iconic “Country Barbie” image, and genuine warmth. Parton stands as one of the finest songwriters not just in country, but across all genres. She masterfully spins narratives often drawn from her own life, including the touching “Coat of Many Colors” about her impoverished East Tennessee childhood, the desperate plea “Jolene,” fearing another woman might take her husband, and, of course, “I Will Always Love You”—written as a farewell to mentor Porter Wagoner long before Whitney Houston transformed it into a global anthem. Added to this is Parton’s unique, angelic vibrato—a voice that seems to float yet possesses remarkable strength and endurance.
Since her 1967 debut Hello, I’m Dolly, Parton—also a renowned philanthropist and theme park owner—has achieved 25 No. 1 hits on Billboard’s Country Songs chart (the most for any female artist) and 49 top 10 albums on the Country Albums chart, including nine No. 1s, most recently with 2023’s Rockstar. At 78, the universally beloved entertainer remains at the peak of her creative powers, solidifying her position as arguably the greatest and most popular country singer of all time. – M.N.
