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Billboard's staff picks the greatest country songs of the past century that have made us love, cry, drink and dance.
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Katie Atkinson, Katie Bain, Dave Brooks, Kyle Denis, Thom Duffy, Josh Glicksman, Paul Grein, Lyndsey Havens, Elias Leight, Jason Lipshutz, Joe Lynch, Rebecca Milzoff, Taylor Mims, Melinda Newman, Jessica Nicholson, Glenn Peoples, Deborah Evans Price, Kristin Robinson, Andrew Unterberger, Christine Werthman, Xander Zellner
Charley Pride, Dolly Parton, George Jones, The Chicks and Shania Twain Michael Putland/Getty Images; Valerie Macon/Getty Images; Michael Ochs Archives/Getty Images; Ron Wolfson/Getty Images; John Atashian/Getty Images
In many ways, country music tells the story of America.
There is the celebration of rural life and the yearning to recapture a seemingly simpler time. There are murder ballads, cheating songs, tunes that herald Saturday night’s debauchery and Sunday morning’s redemption. There are bring-you-to-your knees, heartbreak songs and songs that embrace both fleeting and everlasting love.
In the roughly 100 years that country music has been recognized as its own distinct genre in the U.S., there have been thousands of songs that have left their mark on the culture, and on fans’ memories.
Country music is rooted in storytelling and the decades are filled with songs that have defined a movement and artists whose arrival has helped usher in a new sound. Some songs have delivered messages that lodged inside our brains and hearts, while others have provided a lighthearted moment or just reminded us to raise our glass. Though there is certainly great musicianship involved, the story a country song tells is usually what makes it more memorable than a specific piano run or guitar riff — the obvious exception being the instantly recognizable opening chords to “Friends in Low Places,” which still sends fans into a frenzy.
The 100 songs ranked below were voted on by the Billboard editorial staff. A few caveats: We could have easily gone way longer, as there is no shortage of memorable songs in the country canon, and there was spirited debate over what we put on and left off. We also stuck to a more traditional definition of country, not veering too far into Americana, bluegrass or folk.
Also, whether fairly or not, the list is weighted heavily toward older songs because they have the advantage of time proving their legacy and enduring appeal.
Regardless of when they were released in the last century or this one, each of these songs has moved millions of people and, like great songs in any genre or era, made the listener feel something — even if it’s simply less alone for a few minutes.
Below are Nos. 100-76. Each day, we will roll out another 25, with the No. 1 song revealed on Thursday (May 8.)
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100. Rascal Flatts, “Bless the Broken Road”
While many artists have recorded “Bless the Broken Road” since it was written in 1994 by Marcus Hummon, Bobby Boyd and Jeff Hanna, Rascal Flatts’ heartfelt version of the genial love song about how all heartbreaks are just stepping stones leading to Mr. or Ms. Right emerged as the clear frontrunner. It not only became the group’s highest-charting hit, by topping Hot Country Songs for five weeks, but also helped the songwriters to earn a Grammy, taking home a win for best country song at the 48th annual ceremony, where the crossover smash was also nominated for song of the year. — LYNDSEY HAVENS
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99. LeAnn Rimes, “Blue”
A few years before her country-pop crossover in the late ‘90s, a 13-year-old LeAnn Rimes wowed Nashville with her take on “Blue,” the heart-wrenched standard released by Bill Mack decades before Rimes was born, but which Rimes fashioned into a belated top 40 hit on the Hot 100 chart. The teen singer/yodeler imbues lines like “Three o’clock in the morning, here am I/ Sitting here so lonely, so lonesome I could cry” with a weariness well beyond her years, and sinks into the titular word with a wounded howl. No one who heard this rendition was surprised by the stardom that was soon to follow. — JASON LIPSHUTZ
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98. Eric Church, “Drink in My Hand”
Image Credit: Courtesy Photo There were countless country music odes to alcohol before “Drink in My Hand,” but few have matched the energy of this undeniable weekend warrior anthem when it popped its top in 2011. “Drink In My Hand” would become Eric Church’s first No.1 on the Hot Country Songs chart and usher in an era of boozy, rock-influenced call-and-response radio hits. Today, “Drink in My Hand” and its instantly recognizable opening guitar riff are a high point of Church’s legendary live show, letting fans know it’s time to get on their feet, hoist their drinks in the air and raise a little hell. — DAVE BROOKS
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97. Skeeter Davis, “The End of the World”
It’s never a good sign if you’re watching a sci-fi movie or a retro-set drama and “The End of the World” starts wafting into the background: chances are some pretty serious s—t’s about to go down. Skeeter Davis’ crossover 1963 ballad has been consistently soundtracking cataclysmic events in film and television for six decades, not just for its apocalyptic title, but for the equivalent level of devastation evident in Davis’ innocent voice — so pained that when it splits into harmony at the end of the refrain, it sounds like it’s actively fracturing. There’s no greater musical shortcut to suggesting a universe on the precipice of total annihilation: just metaphoric, if you’re lucky. — ANDREW UNTERBERGER
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96. Old Crow Medicine Show, “Wagon Wheel”
The story of one of country music’s greatest singalongs, “Wagon Wheel,” is a roundabout one: The song’s chorus was originally written by Bob Dylan in 1973. While he never officially released it, Dylan’s song sketch, then titled “Rock Me Mama,” made it into the hands of high school student Ketch Secor of Old Crow Medicine Show, who was studying at the elite New England boarding school Phillip Exeter and “feeling homesick for the South.” Secor wrote some verses to the Dylan tune, and the rest is history. To date, it’s the band’s greatest hit, and it brought to even greater ubiquity through a 2013 cover by Darius Rucker. Now, it’s so overplayed, there are even reports that some events like the New England Americana Festival have placed a ban on the catchy country tune. — KRISTIN ROBINSON
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95. Lee Greenwood, “God Bless the U.S.A.”
There’s a handful of things that are stereotypically associated with a classic country song: trucks, beers, and pride in being an American. “God Bless the U.S.A.” may only have the latter, but it’s arguably the most universal of the three and has become a patriotic anthem that has expanded far beyond the country audience. Though Greenwood has sung it for both Republican and Democratic presidents after performing it at the 1984 Republican National Convention and the song was revived following 9/11, in recent years it has become widely embraced almost exclusively by the right, despite Greenwood’s originally intentioned universal message. — L.H.
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94. Tom T. Hall, “(Old Dogs, Children and) Watermelon Wine”
The late Tom T. Hall will forever be known as one of country music’s greatest storytellers, and this classic hit perfectly demonstrates why. Hall wrote the song after an encounter with an elderly janitor at a Miami Beach Hotel, sharing the man’s assessment that there “ain’t but three things in this world that’s worth a solitary dime — but old dogs, children and watermelon wine.” Released in 1972 as the second single from his album The Storyteller, Hall took the song to the top of the chart and earned two Grammy nominations, for writing and performance. — DEBORAH EVANS PRICE
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93. Morgan Wallen, “Whiskey Glasses”
Morgan Wallen poured himself out a big glass of classic country in this salute to the temporary heart-healing properties of alcohol. Writers Ben Burgess and Kevin Kadish’s clever double entendre wordplay on whiskey glasses to drink from and whiskey glasses to look through — both of which can numb the pain — propelled the song to No. 1 on Billboard’s Hot Country Songs chart. Wallen first placed the tune on his first EP, but it didn’t become a hit until it was released as a single from his breakthrough full-length set, 2018’s If I Know Me, ultimately leading Billboard’s 2019 Top Country Airplay year-end tally and propelling Wallen toward superstardom. — MELINDA NEWMAN
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92. The Chicks, “Goodbye Earl”
Image Credit: Courtesy Photo Two good girls dream of life beyond their small town; one marries a domestic abuser; she feeds him some poisoned black-eyed peas, dumps his body in a lake and takes off into a sunset of her own creation — the dark humor of “Goodbye Earl” sounded like it had sprung straight from The Chicks’ hivemind when the trio released the acid-tongued follow-up to “Cowboy Take Me Away” in early 2000. In fact, the not-so-classic murder ballad was written by country veteran Dennis Linde (known for penning Elvis’ “Burning Love”). Still, its gimlet-eyed take on storybook romance and biting one-liners, wrapped in Natalie Maines’ magnetic sass and side-eye, perfectly encompass The Chicks’ ethos — and the group’s keen understanding that creating a perfect country hit didn’t preclude occasionally giving tradition the finger. — REBECCA MILZOFF
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91. Kacey Musgraves, “Follow Your Arrow”
With a little bit of twang and Musgraves’ signature touch of pop, Musgraves’ breakthrough 2013 single is a winner on instrumentation alone, but it’s her honest lyrics about being yourself that turn this simple song into an anthem for outsiders. The song explains that “You’re damned if you do, and you’re damned if you don’t” when it comes to other people’s judgment, so just kiss the boys or the girls that you like, roll a joint (or don’t) and just be who you are. — TAYLOR MIMS
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90. Deana Carter, “Strawberry Wine”
Written by Matraca Berg and Gary Harrison, this nostalgic coming-of-age tale became Carter’s biggest hit, winning song of the year at the 1997 CMA Awards and reaching No. 1 on Billboard’s Hot Country Singles and Tracks chart. Carter’s sweet, lilting twang perfectly married with the cinematic lyrics about a girl experiencing a sexual awakening and the woman who looks back at the time with bittersweet memories of a love and relationship that didn’t last, but a beautiful memory that did. — M.N.
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89. Martina McBride, “Independence Day”
With a backdrop of patriotic imagery (“let freedom ring,” “dawn’s early light,” “talk about your revolution”), this song of reckoning was written by Gretchen Peters from the perspective of a child in an abusive home and a mother’s journey to escape it. McBride is the perfect narrator for the harrowing-turned-empowering story, with her powerhouse vocals perfectly building to the chorus’ cathartic moment of emancipation. The song’s message continues to resonate to this day, as McBride has been a longtime spokesperson for causes like the National Domestic Violence Hotline and the National Network to End Domestic Violence. — KATIE ATKINSON
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88. DeFord Bailey, “Pan American Blues”
Despite the deep segregation plaguing the South, the first solo star to emerge from the Grand Ole Opry was a Black harmonica player named DeFord Bailey, who was also the first Black artist to ever play the then-new institution. Titled after the Pan-American, a passenger train that ran between New Orleans and Cincinnati, “Pan American Blues” is an inventive instrumental where Bailey bends and blows the bluesy notes on his harmonica to conjure up the sound of a chugging train building up to breakneck speeds. The 1927 recording was one of the biggest sellers of the genre’s early years, and the Tennessee harp whiz’s popularity in the ’30s went a long way toward establishing the Opry and Nashville as hubs for the country music business. —JOE LYNCH
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87. Lady A, “Need You Now”
Image Credit: Courtesy Photo The list of country songs that have made noise in the Big Four categories of the Grammy Awards during the 21st century is extremely short, but Lady A’s “Need You Now” — which won a total of four trophies at the 2011 ceremony, including record of the year and song of the year — demonstrated the song’s stature and became a rare exception. The Nashville trio’s ode to late-night longing remains a country-pop monster, with the type of dual-vocal chorus ripe for top 40 radio and karaoke duets, but plenty of spiraled-out guitar chords to reflect a lonesomeness steeped in country tradition. — J. Lipshutz
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86. Lee Ann Womack feat. Sons of the Desert, “I Hope You Dance”
At the turn of the century, Lee Ann Womack and country group Sons of the Desert joined forces for one of the most moving ballads in contemporary country music. Often thought to be a message to a child from their parent, “I Hope You Dance,” written by Mark D. Sanders and Tia Sillers, is a lot more open-ended. When Womack sings of giving “the heavens above more than just a passing glance,” she’s talking to anyone and everyone at the same time, effortlessly pulling off popular music’s eternal balance of the personal and universal through the lens of wistful country-pop production. The whole song is a masterclass in vocal storytelling, but when Womack takes an extended beat after the bridge before dropping the “I hope you” and simply belting “dance,” her switch from dreams to directives lifts the song to a staggering emotional apex. — KYLE DENIS
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85. Vince Gill, “Go Rest High on That Mountain”
Vince Gill may have written this song specifically to honor the deaths of fellow artist Keith Whitley and Gill’s older brother, but he ended up penning a gorgeous, emotional tribute with universal appeal that has only grown in stature as a funeral standard over the past 30 years. And for good reason: The combination of Gill’s otherworldly, high lonesome voice combined with the song’s lyrical pairing of grief with exaltation has led to a new staple — one that feels as sacred and eternal as the afterlife he sings about. — M.N.
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84. Alan Jackson, “Where Were You (When the World Stopped Turning)”
With the exception of artists like Johnny Horton, who recorded such songs as “The Battle of New Orleans” and “Sink the Bismarck” or Loretta Lynn’s “Dear Uncle Sam,” country songs about specific historic events are relatively rare. And before “Where Were You,” Alan Jackson had never tackled such weighty world matters. But Sept. 11, 2001, was a day that changed everyone’s life. While some other country artists approached that horrific day with patriotic verve such as Darryl Worley with “Have You Forgotten,” Jackson approached it from a purposefully unpolitical stance and from one that simply asked how the listener made it through that day. He debuted his every-man take — full of sadness but also ringing with hope — at the 2001 CMA Awards in November. At the next year’s ceremony, it took home single and song of the year. — M.N.
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83. Little Big Town, “Girl Crush”
Image Credit: Courtesy Photo There’s a retro, ballad-like quality to “Girl Crush” that, despite dropping in 2014, would sound just as much at home on the Grease soundtrack. The longing and desire that is baked into each line is palpable – largely because it’s so relatable. To write a love song that has so little to do with the man in the equation felt refreshingly rare at the time – and to toe the line so smartly between hating the girl in the equation and wanting to be her is what helps this song hit just as hard over a decade later. — L.H.
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82. Dwight Yoakam, “Guitar & Cadillacs”
Dwight Yoakam’s neo-honky tonk sound didn’t fit the Urban Cowboy music coming out of Nashville in the early ‘80s, so the Kentucky native decamped to Los Angeles — taking musical inspiration from a town up the road, Bakersfield, and one of its favorite sons, Buck Owens. Yoakam became ensconced in Los Angeles’ music scene, but the “lonely streets” and “wasted lives” of Tinsel Town found him looking for comfort in the guitars, Cadillacs and hillbilly music of his roots. With its upbeat shuffle and guitarist Pete Anderson’s masterful picking, “Guitars & Cadillacs” was a hit with audiences, reaching No. 4 on Billboard’s Hot Country Songs chart in 1986, and remains a cornerstone of Yoakam’s concerts to this day. — GLENN PEOPLES
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81. Conway Twitty & Loretta Lynn, “Louisiana Woman, Mississippi Man”
True love has rarely sounded more capable of overcoming a challenge than it does in the lyric to this upbeat hit by Conway Twitty and Loretta Lynn. Written by Becki Bluefield and Jim Owen, the song describes two lovers separated by the Mississippi River but determined to be together even if they have to swim the mile-wide divide. Released in May 1973, the song appeared on the pair’s chart-topping album of the same name and became Twitty & Lynn’s third No. 1 single as a duo on Billboard’s Hot Country Songs chart. — D.E.P.
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80. Hank Williams Jr., “Family Tradition”
When Hank Williams Jr. released “Family Tradition” in 1979, the song initially reached the top 5 on Billboard’s Hot Country Songs chart — but it has since become one of country music’s most iconic party anthems. By taking pride in rowdy moments of drinking, smoking and the like and referring to them as a “family tradition” — and then backing it with his hard-charging, bluesy-rock honky-tonk sound — Williams created a song that has become a favorite at concerts, football games and karaoke nights alike, with fans aiding in fashioning the song’s now iconic call-and-response chorus.— JESSICA NICHOLSON
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79. Bob Wills, “San Antonio Rose”
Swing was king when country began to codify as a genre, so it was only natural that savvy bands like Bob Wills and His Texas Playboys would split the difference. Melding jazz, orchestral pop, folk and “hillbilly music,” the fiddle-wielding Wills and his crew found massive success during the ‘30s and ‘40s, and this was their signature tune. With a sweet, lilting, lovelorn melody (not to mention Wills’ helium-pitched cries of “aaaah-haaa” popping up throughout), “San Antonio Rose” painted a romantic picture of love and loss under the Texas stars, popularizing a theme that still permeates through country music today. — J. LYNCH
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78. Sam Hunt, “Body Like a Back Road”
Image Credit: Courtesy Photo In retrospect, “Body Like a Back Road” sounds like a harbinger of the hip-hop-adjacent country hits to follow: two years before Lil Nas X and Billy Ray Cyrus were traveling to chart history with “Old Town Road,” Sam Hunt was utilizing Mustard-esque “hey’s” in the back half of the “Back Road” chorus. Yet removed from its cultural significance, Hunt’s smash, which crossed over to become a top 10 hit on the Billboard Hot 100, remains an effortlessly charming bit of flirtation — on lines like “The way she fit in them blue jeans, she don’t need no belt/ But I can turn them inside out, I don’t need no help,” you can hear him smiling, giddy in his slick delivery. — J. Lipshutz
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77. Eddy Arnold, “Make the World Go Away“
The cold-open here features one of the most world-weary passages ever recorded: “Make the world go away/And get it off my shoulders.” Ray Price was the first artist to record this tear-stained Hank Cochran ballad, taking it to No. 2 on Hot Country Songs in 1963. But Price’s version stalled at No. 100 on the Hot 100, losing a cover battle to a pop version by Timi Yuro. In 1965, Arnold turned it into a smash in both markets. His version, produced by veteran hitmaker Chet Atkins, topped Hot Country Songs for three weeks and reached No. 6 on the Hot 100. — PAUL GREIN
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76. Emmylou Harris, “Boulder From Birmingham”
From the plaintively sung first line (“I don’t want to hear a love song”) Harris’ quivering silver soprano offers a lesson in quiet devastation in this tribute to her mentor and country-rock forebear, Gram Parsons. Its soulful refrain — “I would rock my soul in the bosom of Abraham/ I would hold my life in his saving grace/ I would walk all the way from Boulder to Birmingham/ If I thought I could see, I could see your face” perfectly encompasses the boundless feeling of grief in terms both religious and geographical. That Joan Baez would later cover it feels spiritually appropriate: like Harris’ best work, “Boulder” has the timeless feel of a folk song, delivered in an inimitably gorgeous voice. — R.M.
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