Country music is renowned for its legendary figures like Merle Haggard, Willie Nelson, Loretta Lynn, and many others. Mentioning their names instantly brings to mind their unique voices, personal styles, and the iconic songs they popularized.
These artists didn’t just contribute to the genre; they fundamentally shaped it.
Although country music encompasses various sub-genres, it predominantly revolves around the acoustic guitar and other string instruments like the fiddle, steel guitar, banjo, and mandolin. As the late songwriter Harlan Howard famously put it, great songs often come down to “three chords and the truth.”
When evaluating the top country singers, one must look beyond metrics like record sales, streaming numbers, and sold-out concerts, although those are significant too.
These leading country singers are distinguished by their unique voices that, unlike anyone before or after them, vividly convey the emotion, message, and stories embedded in the songs that made them who they are.
Top Country Singers of All Time
Taylor Swift
Taylor Swift was bound to abandon country music in favor of pop; her celebrity status could not be confined to a single genre. Swift, who was born in Pennsylvania and raised in Nashville, had a mark on country radio before the age of 18, with “Tim McGraw” being a Top 10 success and “Our Song” becoming her first country number one in 2007.
By the time she incited Kanye West’s fury at the 2009 VMAs, she was already playing to a different tune than her colleagues, and following albums Fearless and Red brought her even more attention. Nonetheless, her deliberate departure from the genre that propelled her ahead of 2014’s breakthrough in 1989 left some wishing she had maintained one foot in the country. “Love you, mean it,” Swift stated in a 2014 Rolling Stone cover story, “but this is how it’s going to be.”
Brad Paisley
Brad Paisley stands out as the poster boy for the genre’s long-standing traditions. The West Virginian is one of the greatest artists of the 21st century, with 19 songs topping the country charts, several of which, like “I’m Gonna Miss Her (The Fishin’ Song)” and “She’s Everything,” immediately connected with listeners. Paisley’s 2009 album American Saturday Night positioned him as a forward-thinking country musician, and his success was only matched by his record sales.
His guitar skills make him the country’s Eddie Van Halen, and he’s also one of the most astute composers of his time. As he approaches middle age, his star-studded Love and War (his eleventh straight Number One album) has reinforced another old-school concept in 2017: growing old gracefully.
Kenny Rogers
He began as a pop performer with his group The First Edition before becoming even more popular when he switched to country music. Kenny Rogers was great at utilizing his golden tones to convey a tale via music. One of the most powerful instances is seen in “The Gambler.”
Nonetheless, he continued to do so with “Lucille,” “Lady,” and his duet with Dolly Parton on “Islands in the Stream.” Between 1977 and 1987, Rogers had songs that reached number one. The Houston native’s career lasted six decades until he died in 2020 at the age of 81.
Reba McEntire
She is one of the most successful female musicians in country music history, having sold over 58 million records. Reba McEntire’s Oklahoma roots suited her well for country music. She grew up in rodeos and even participated in barrel racing. When she performed the National Anthem at the National Rodeo Finals, she drew the attention of a Nashville music publisher.
Since beginning her career, her megahits have included “Color Me Gone,” “I’m a Survivor,” “Fancy,” and others. She has more No. 1 country albums than any other female singer and has also achieved success as an actress, novelist, and entrepreneur.
Randy Travis
His deep voice breathed life into songs like “Forever and Ever Amen,” “Deeper Than The Holler,” “I Told You So,” and others. Randy Travis went to Nashville from North Carolina and rose to prominence in the music industry in the 1980s.
With his basic, conventional approach, he rose to prominence in country music over the following 25 years. Travis had a devastating stroke in 2013 and is no longer able to perform, although he continues to appear in and around Nashville, often on stage at places such as the Grand Ole Opry. Travis is well-liked and adored by both country music fans and other performers.
Jerry Jeff Walker
Though not a native Texan, Jerry Jeff Walker was one of the performers who helped place the Lone Star State, and specifically Austin, on the country music map in the 1970s. Walker’s best-known tune was 1968’s “Mr. Bojangles” (a Top 10 pop smash for the Nitty Gritty Dirt Band), but he was immortalized five years later with the seminal live album Viva Terlingua!
Terlingua’s Tejano-infused “gonzo country” (his crack backing band, including Gary P. Nunn and Bob Livingston, were dubbed the Lost Gonzo Band) was more Texas than the outlaws themselves and became a cornerstone of Red Dirt country music.
Loretta Lynn
She was not just a “Coal Miner’s Daughter,” but much more. Loretta Lynn was raised in impoverished Eastern Kentucky, married as a youngster, and had four children before turning twenty. With grit and dedication, she trained herself to play the guitar, create songs, and develop her own vocal style.
Many of her songs, soulfully performed with the heavy Kentucky accent she never lost, were personal and focused on the feminine viewpoint. Hits included “You Ain’t Woman Enough,” “Don’t Come Home A Drinkin,” and many more. Patsy Cline, a friend, helped guide her through the early phases of her career, offering advice on how to flourish as a female vocalist in a male-dominated music industry. Jack White, a singer and guitarist, exposed Lynn to a new generation of music listeners when he produced her 2004 album Van Lear Rose.
Chris LeDoux
The cowboy lifestyle is a prominent theme in country music, almost to the point of cliché, yet that is the one that Chris LeDoux lived. A bareback national rodeo champion, the Wyoming native’s ranch songs were authentic, and he played the role of the maverick to perfection, refusing to sign a record contract because he chose to play by his own rules.
Until that is, Garth Brooks’ shout-out in “Much Too Young (To Feel This Damn Old)” made it too tempting not to cash in. Their later duet, “Whatcha Gonna Do With a Cowboy,” helped give LeDoux the recognition he deserved, and his mystique has only increased since his tragic death from cancer aged 56 in 2005.
Merle Haggard
Merle Haggard, known as the “working man’s poet,” established a musical legacy that was deeply rooted in country but also influenced by blues, pop, jazz, and folk. He created songs about suffering and hardship, overcoming adversity, and dealing with everyday obstacles. He “lived” everything he wrote.
The Bakersfield, California native lost his father at an early age, which led to turbulent adolescent years that often resulted in incarceration. Haggard was spending time at San Quentin in 1958 when he saw Johnny Cash play for the inmates. Haggard will subsequently have a successful solo music career. Just a few of his many songs include “Mama Tried,” “Silver Wings,” “If We Make It Through December,” and “Okie From Muskogee.”
Lucinda Williams
“Shouldn’t I have all this?” Lucinda Williams asks in her hallmark song “Passionate Kisses,” and few lyrics capture the Louisiana native’s singular perspective better. Williams, a consummate perfectionist, has made a profession of delaying gratification, frequently spending years perfecting her albums; her masterpiece, 1998’s Car Wheels on a Gravel Road, took six years to complete.
That resulted in years of cult adulation but little of the widespread recognition “the female Bob Dylan” deserved. But that’s just as well since Williams’ raw voice is one of the most identifiable, and it’s all her own. “I’m a bit of an outlier. I was found late. “And here I am, at my age,” she said earlier this year. “I have to do this.”
Crystal Gayle
Brenda Gail Webb, unlike her Kentucky-born elder sister Loretta Lynn, grew up in Indiana, developing a polished demeanor and vocal style ideal for country-pop crossover. “I went middle-of-the-road because Loretta said, ‘Don’t sing my songs and don’t sing anything I would sing, because you’ll be compared,'” Gayle said to Rolling Stone in 2014. “She was correct.
I wouldn’t have made it if I had just done that. But I adore those tunes.” Gayle’s early singles barely made the charts, but in the late 1970s and early 1980s, she found her stride. The Grammy-winning “Don’t It Make My Brown Eyes Blue” was a country chart-topper and a Number Two pop hit, followed by two more Top 20 pop songs and a total of 18 country No. 1s. In addition to her country background, she has produced refined interpretations of pop songs and was inducted into the Grand Ole Opry in January 2017. Stephen L. Betts
Hank Williams
Despite his terrible death at the age of 29, Hank Williams established the benchmark as a singer and composer that musicians continue to aim for today. The Alabama native was dubbed the “Hillbilly Shakespeare” for his ability to express emotion via lyrics in novel ways. And his twangy, soulful voice elevated each of his tunes to the next level.
Songs like “Your Cheatin’ Heart,” “I’m So Lonesome I Could Cry,” and “Cold, Cold Heart” convey anguish. Williams’ music remains relevant today, more than 70 years after his death.
Lynn Anderson
The North Dakota-born Lynn Anderson’s country career was launched by her mother, Liz Anderson, who composed Merle Haggard’s breakout song “(My Friends Are Gonna Be) Strangers,” which introduced her to the president of her first record company.
Anderson also had many appearances on The Lawrence Welk Show throughout her adolescence, which helped catapult songs like the mournful but joyful “If I Kiss You (Will You Go Away)” into the national Top 10. She relocated to Nashville in 1970, and a year later, she topped both the country and mainstream charts with “Rose Garden,” a no-frills hymn to living in the present featuring her brassy vocals.
Her streak of country singles, which included her interpretation of the Carpenters’ effervescent “Top of the World” and the sassy “What a Man My Man Is,” lasted into the mid-1970s. In the 1980s, she returned to the country Top 10 with “You’re Welcome to Tonight,” a duet with suave singer Gary Morris. Her last album, Bridges, which includes a gospel-tinged rendition of the dreamy Dobie Gray hit “Drift Away,” was released a month before she died in 2015.
Dolly Parton
Dolly Parton is one of the most popular country musicians of all time, thanks to her warm, warbly voice and great talent for songwriting. She’s also among the most honored. Parton has won 11 Grammys and had almost 50 nominations.
She began her career on the Porter Waggoner program in the late 1960s before branching out on her own. She has written and sung dozens of songs, including “Coat of Many Colors,” which is based on a real tale from her childhood, “Jolene,” which has been covered by many other musicians, and “I Will Always Love You,” which was rerecorded as a No. 1 hit by Whitney Houston in 1992.
Parton is a singer, songwriter, multi-instrumentalist, actress, author, philanthropist, and successful entrepreneur. She is also a Country Music Hall of Fame member and one of the Rock and Roll Hall of Fame’s most recent honorees.
Patty Loveless
Patty Loveless performed (with Vince Gill) at George Jones’ funeral. That was fantastic. Loveless’ breakout record was a cover of Jones’ “If My Heart Had Windows,” and the legend’s last success was a duet with Loveless called “You Don’t Seem to Miss Me.” From the late 1980s to the majority of the 1990s, Loveless combined her origins in Appalachian bluegrass with Jones’ current honky-tonk countrypolitan, resulting in a series of songs that updated traditional sounds.
Her ballads (“Don’t Toss Us Away,” “Lonely Too Long”) made adults cry, but her rapid ones (“Chains,” “I Try to Think about Elvis”) provided a cure for tears on the dancing and via singing along. Loveless is now unable to purchase a hit. But that doesn’t mean George Jones’ most devoted disciple isn’t still the finest country singer alive.
Lee Ann Womack
“I Hope You Dance” will always be the song that casual fans know with Lee Ann Womack, but the Texas native is much more than that adult contemporary crossover success. She established herself as a composer in Nashville in the 1990s, authoring Ricky Skaggs’ “I Don’t Remember Forgetting.” Her self-titled debut came in 1997, producing her first hit, “The Fool,” but it was nothing compared to the triumph of “I Hope You Dance” three years later.
Womack would never achieve such heights again, which may be for the best, since she has now reverted to her more conventional roots with The Way I’m Livin’ (2014). “I’m more drawn to songs written at 2 a.m. on the back of the bus than I am the songs written by four or five people at a 10 a.m. appointment,” she told Rolling Stone at that moment.
Tim McGraw
McGraw is one of the most diverse singers on our list, with songs ranging from ’90s dance numbers like “Indian Outlaw” to tear-jerking ballads like “Don’t Take The Girl” and the poignant “Live Like You Were Dying.” He’s also not hesitant to push his limits, as seen by duets with hip-hop singer Nelly.
McGraw has also established himself as an actor in Hollywood, producing strong performances in films such as Friday Night Lights and the Oscar-winning The Blind Side, going above and beyond just portraying a singer on screen like many of his colleagues.
Keith Whitley
Keith Whitley’s country career was brief, consisting of just two albums and a handful of songs throughout his lifetime, yet he is remembered as one of the most important and tragic individuals in genre history. Whitley was born and bred in Kentucky, and as a young man, he joined bluegrass icon Ralph Stanley’s band, where he quickly rose to the lead vocalist position.
Beginning his solo career in the early 1980s, he achieved critical praise and commercial success with the 1988 album Don’t Close Your Eyes, which combined a traditional bluegrass-country voice with modern production.
However, one year later, the 33-year-old artist died at the peak of his abilities, the result of alcohol poisoning. Even so, emotionally charged songs such as “Don’t Close Your Eyes,” “When You Say Nothing at All,” and “I’m No Stranger to the Rain” have become country standards, and Whitley has been hailed as an influence by singers ranging from Vince Gill and Chris Young.
Ray Price
In a recording career spanning six decades, “The Cherokee Cowboy” had a voice that never appeared to age. If anything, his soft crooning tone only improved with time. Price’s early singles were classic honky-tonk performances, but 1967’s “Danny Boy” introduced a more uptown tone, which he elaborated on in hits like Kris Kristofferson’s “For The Good Times.” Price had a strong ear for other talent, offering Willie Nelson and Roger Miller early opportunities, among others.
Emmylou Harris
Harris, country’s definitive harmony vocalist and songfinder, has left a powerful emotional fingerprint on hundreds of albums (hers and others) for decades. “The way individuals pronounce words and syllables is much more significant to me than the components. “It’s a matter of feeling,” Harris told Rolling Stone in 1978 about her vocal contributions.
Harris began a two-decade run with Warner Bros., taking interpretations of hits by Buck Owens (“Together Again”) and Patsy Cline (“Sweet Dreams”) to Number One and making superstars of her Hot Band members, including Rodney Crowell and Ricky Skaggs. She collaborated with Linda Ronstadt and Dolly Parton on the long-awaited Trio album in 1986, and with producer Daniel Lanois on 1995’s dramatic, needle-moving Wrecking Ball, which foreshadowed her increasing dependence on her own smart songwriting.
