Best Country Songs of All Time: 100 Staff Picks

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

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

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

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

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

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.

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

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

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

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 

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.

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

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

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

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

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.

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.

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.

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

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.

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. Williams acknowledges ambition for making music distinct from the sound his famous country music legend father made, and accepts that in the process, he may have riled some within the country music ranks–or as he sings, “some of my kinfolks have disowned a few others and me.” Still, he takes pride in rowdy moments of drinking, smoking and the like. 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

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

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

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

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.

Toby Keith’s debut single introduced listeners in the early 1990s to his steady baritone and his appreciation for the bygone days. With references to the TV show Gunsmoke, outlaw Jesse James and movie cowboys Gene Autry and Roy Rogers, Keith sets the stage for his lamentations: “I should’ve been a cowboy/ I should’ve learned to rope and ride/ Wearin’ my six-shooter/ Ridin’ my pony on a cattle drive.” The song became Keith’s first Hot Country Song No. 1, and while he might have missed his opportunity to sleep “out all night beneath the desert stars,” “Cowboy” put him on the path to becoming a shining star of his own making. — CHRISTINE WERTHMAN

Clocking in at over five minutes long, this David Allan Coe classic was penned by Steve Goodman and John Prine, although Prine asked not to be credited because he considered it a “goofy, novelty song.” He was right, but that’s part of its fun, enduring appeal. Goodman released it in 1971 on his eponymous debut album, but it was Coe’s version, recorded on his 1975 Once Upon a Rhyme album, that gained traction. The song became Coe’s first top 10 hit on Hot Country Songs, peaking at No. 8. The lyric makes a playful claim to be the “perfect country and western song,” thanks to the self-aware inclusion in the climactic final verse of such country staples as mama, trains, trucks, prison and getting drunk. — D.E.P.

When first released in 1972 performed by its writer, the Lone Star State songwriting legend Townes Van Zandt, “Pancho and Lefty” went largely unnoticed. Then, thanks to Emmylou Harris’s cover in 1977, Willie Nelson and Merle Haggard heard the tune, and opted to turn it into a star-powered duet in 1983. It’s a classically Western tale: an ambitious young Pancho travels south of the border to make a fortune, only to resort to a life of crime. Sold out to the “federales” by his friend Lefty, Pancho is killed, and Lefty’s left with his regrets forevermore. With Haggard and Nelson’s rendition, the spellbinding song finally got the credit it deserved — and to take it full circle, the duo honored Van Zandt by casting him as the captain of the “federales” in the music video. — K.R. 

It might not make sense on paper to have a teenager perform a song about a faded beauty still clinging to her youth, but Tucker’s throaty delivery of the heartbreaking tale bewitchingly belied her 13 years. The song – written by Larry Collins and Alex Harvey – was inspired by the death of Harvey’s mother, who was from the Mississippi Delta and “always lived her life as if she had a suitcase in her hand but nowhere to put it down.” While “Delta Dawn” was also recorded by Bette Midler and was even a Hot 100 No. 1 for Helen Reddy, it was Tucker who first turned it into a Nashville smash, earning her first Grammy nomination, her first Hot Country Songs top 10 and her ticket to stardom along the way. – K.A.

Yearwood created an enduring classic in 1993 when she released this song that pays homage to the power of music. Written by Hugh Prestwood, the track, which reached No. 2 on Hot Country Songs, captures how a perfect song at an unexpected time instantly triggers the memory of a long-forgotten romance. “When I heard that old familiar music start/ It was like a lighted match had been tossed into my soul,” Yearwood sings, her rich, crisp voice, accompanied by a pared-back piano arrangement, which serves as perfect foil for this elegant song. — J.N.

Is there a more heartbreaking song in all of country music than “Whiskey Lullaby?” Maybe “He Stopped Loving Her Today,” but it’s a close call. Penned by Bill Anderson and Jon Randall, in the first half a brokenhearted man drinks himself to death. Then in the second half, the guilt-ridden woman who had tossed him out dies the same way. “He put that bottle to his head and pulled the trigger” is a full story in one line. There is no relief in the song, except that the couple is no longer in pain, but the sorrow never lifts. “Whiskey Lullaby” took home song of the year at the 2005 CMA Awards, with good reason. Twenty years later, it’s still impossible to hear it without feeling kicked in the gut. — M.N.

Backed by the Jordanaires and armed with her signature wit, Loretta Lynn crashed the Hot 100 and challenged country radio’s conservatism with this ode to birth control pills in 1975. “The Pill” utilizes warbling guitars and a fiery vocal to capture the freedom women can find through having control over their own bodies. “But all I’ve seen of this old world is a bed and a doctor bill/ I’m tearing down your brooder house ’cause now I’ve got the pill,” she declares in the opening verse. Over 50 years later, “The Pill” reminds us of how far women in music have come – and how far we’ve regressed in understanding and internalizing how American music is often innately political. — K.D.

This 1973 hit is classy and sensuous in equal measure, much like the woman Rich is singing about. This is one of the best examples of producer Billy Sherrill’s “countrypolitan” approach – blending elements of country and pop to appeal to a wide audience. The song, written by Kenny O’Dell, topped Hot Country Songs for two weeks and cracked the top 15 on the all-genre Hot 100. “Behind Closed Doors” was an awards magnet, winning both single and song of the year at both the CMA and ACM Awards, as well as two Grammys. It also received Grammy nods for both record and song of the year, a rarity then (and now) for a country hit. — P.G.

This poignant song flips the idea of a “death sentence” on its head, suggesting that everyone could actually get a new lease on life if they lived as if every day were their last. Sure, there are the fun bucket-list dreams in the rollicking ballad, like skydiving and lasting “2.7 seconds on a bull named Fu Man Chu,” but more importantly, there’s the quality time with friends and family, reaching for a deeper love and the willingness to forgive. The Tim Nichols and Craig Wiseman-written hit was the longest-running Hot Country Songs No. 1 of 2004 (with seven weeks atop the chart) and scored McGraw his second Grammy (for best country song). – K.A.

Jerry Lee Lewis, Linda Martell and Charley Pride were just a few of the artists to record their own versions of “Before the Next Teardrop Falls” in the 1960s, before Freddy Fender stepped in with a major change in 1974. After the opening verse, Fender repeats it again in his native Spanish, transforming what was once an unassuming country ballad into a bilingual Tex-Mex masterpiece. Fender’s gentle, heartbreaking delivery — crooning “it’s your happiness that matters most of all” — turned the nearly 40-year-old Mexican-American singer into a superstar almost overnight. “Teardrop” became his first chart appearance, and the tune shot to No. 1 on both the Hot Country Songs and Billboard Hot 100 charts. At the time it was just the ninth song to top both rankings, and it helped pave the way for the many bilingual, cross-genre hits we see today. —  XANDER ZELLNER

This tender Kris Kristofferson-penned ballad recounts the end of a love affair, conveyed with sadness, regret, and ultimately acceptance. The best of many great lines: “There’s no need to watch the bridges that we’re burning.” Bill Nash was first to record the song in 1968. Kristofferson’s own version appeared on his eponymous debut album in April 1970. Price’s sublime recording topped Hot Country Songs that September, then won both single and song of the year at the ACM Awards. Al Green included a soulful cover version on a hit 1972 album. Kacey Musgraves spoke for many when she said it “might be the saddest song of all time. It really breaks my heart.” — P.G.

As the Grand Ole Opry turns 100 this year, this iconic Roy Acuff hit is sure to be remembered as one of the cornerstones of the famed institution. This 19th-century American folk song about a mythical train was recorded by the Carter Family in 1929, but it was Roy Acuff’s 1936 version that went on to sell 10 million physical copies worldwide. Also recorded by Bing Crosby, Blind Willie McTell and other artists, the song is part of the Rock & Roll Hall of Fame’s 500 Songs that Shaped Rock and Roll and is the oldest song on that list. — D.E.P.

Ronnie Milsap scored one of the biggest songs of his career in 1980 with this gentle ballad about regret and loss that crossed over from country to adult contemporary and pop radio. Milsap leaves LA to return to Tennessee to find his love. She has moved on, but he vows to never stop searching as his tears and rain mingle. There’s a lot of song here with a bridge, an instrumental interlude, strings and sentimental backing vocals that all add to Milsap’s magnificently urgent vocal delivery in this Kye Fleming/Dennis Morgan-penned classic. —M.N.

Released in 1977, this chart-topping Waylon Jennings hit name-checks Mickey Newbury, Jerry Jeff Walker and Hank Williams, and features a guest vocal by longtime friend and fellow Outlaw Willie Nelson on the final refrain. Released as the first single from the album Ol’ Waylon, “Luckenbach, Texas” was written by Chips Moman and Bobby Emmons. The classic singalong looks at the toll “high society” living is taking on a marriage and the protagonist’s simple desire to “get back to the basics of love.” — D.E.P.

It’s surely harder to find someone who hasn’t sat around a campfire swaying and singing this song than someone who has. There’s a comforting ubiquity in it, and despite becoming one of West Virginia’s four official state anthems, “Country Roads” has come to symbolize the idea of home for anyone from anywhere. Its universality – despite the specificity of some lyrics, like “Blue Ridge Mountains, Shenandoah River” – was reflected on the all-genre Hot 100, with the song peaking at No. 2 there, despite only reaching No. 50 on the Hot Country Songs chart. — L.H.

From the ache in the lyric to the mournful tone of Gosdin’s stellar voice, few songs in any genre of music personify heartbreak and loss better than “Chiseled in Stone.” Written by Gosdin and Max D. Barnes, the song chronicles a barroom conversation between a man escaping an argument at home and a man broken by the loss of his wife, who tells him, “You don’t know about lonely till it’s chiseled in stone.” After reaching No. 6 on Hot Country Songs, “Chiseled in Stone” won the CMA for song of the year in 1989. —  D.E.P.

Written by Ronnie Dunn, “Boot Scootin’ Boogie” was first recorded by West Virginia country swing outfit Asleep at the Wheel, but it was Brooks & Dunn’s own 1991 version, from the duo’s debut album Brand New Man, that stuck. The song simply sounds like the country honky tonk conjured in its lyrics, a place filled with the promise of “whiskey, women, music, and smoke.” And while the sound of boots hitting the floor during a line dance isn’t technically included in the recording, it’s almost impossible to listen to this one and not hear them. — KATIE BAIN

What a title: instantly spotlighting the drink that will be at the center of Webb Pierce’s most storied narrative, like a prosecuting attorney launching into his accusatory opening remarks. In truth, Pierce isn’t looking to condemn said glass in this 1953 classic; he does not use his pinched near-falsetto to blame it for his romantic troubles, rather to sheepishly admit his reliance on it in ignoring them. “It’s my first one today,” he claims — and even if that’s true, you know it won’t be his last. The striking vocals, twangy steel guitar melody and too-relatable lyrics of “Glass” even got a refill nearly 70 years later via another country chart-topper: Sam Hunt’s 2020 smash “Hard to Forget,” whose chopped-up samples of Pierce’s original vocal make him sound more winningly pitiable than ever. — A.U.  

In 2009, “In Color” reached the top 10 on Billboard’s Country Airplay chart. Written by Johnson, James Otto and Lee Thomas Miller, this song centers around a grandfather retracing a lifetime of memories. After his grandson asks about some old black and white photos, the man fills in those details that the photos’ “shades of gray keep covered.” The man recalls his family surviving the Great Depression, how he later faced battles alongside a military comrade, and the pride his took in marrying his lover. Johnson’s gravelly voice puts this CMA and ACM Award-winning song of the year in perfect focus. — J.N.

Nitty Gritty Dirt Band’s classic hit has endured thanks to its universal celebration of being young and in love. The oft-covered song follows a couple in the early days of a new romance, when all that matters is being together. The narrator sets the scene in the opening verses (“Lazy yellow moon comin’ up tonight/ I’m gonna take you to a special place that nobody knows”) before practically kicking down the door with his pitch: “YOU and ME goin’ fishin’ in the dark/ Lyin’ on our backs and countin’ the stars.” The narrator’s enthusiasm is infectious as they fall in love throughout the night. Are they actually catching any fish? Are they even fishing? Doesn’t matter. What matters is the two of them are together. The song struck a chord with listeners, becoming the band’s third leader on the Hot Country Songs chart in 1987. — X.Z.

Dean Dillon and Hank Cochran wrote “The Chair” in the middle of the night while sailing around the Bahamas. “By about four in the morning, I had drunk so much whiskey that I had actually drunk myself sober,” Dillon told Texas Monthly in 2014. His offhand remark — “Well, excuse me, but I think you’ve got my chair” — sparked the loping track. Cochran came up with Strait’s famous, incorrectly worded question: “Can I drink you a buy?,” symbolizing not his inebriated state, but his nerves at approaching the woman in the bar.  Strait picked “The Chair” as lead single from his 1985 Something Special album, rendering it as a swaying, sentimental ballad swaddled in strings. It hit No. 1 on the Hot Country Songs chart, marking Strait’s seventh No. 1 in just three years. —  ELIAS LEIGHT

In terms of instantly recognizable, singalong song structure, “Islands in the Stream” writers the Bee Gees’ have their fingerprints all over this one. But Dolly Parton and Kenny Rogers put their own lightly country spin on the 1983 tune, adding a bit of twang and a whole lot of steam with their impassioned, anthemic duet about two lovers who easily fall back into each other’s arms whenever the time is right.  The song hit No. 1 on both Billboard’s Hot 100 and Hot Country Songs charts in the fall of 1983, and was introduced to a new generation (and a whole other genre) 15 years later when it was interpolated in Pras’ 1998 hit “Ghetto Superstar (That Is What You Are).” — K.B.

Country music, like rhythm and blues, has been internationally irresistible for decades. Want proof? Drop the needle on side two, track one of the Beatles’ 1965 album Help!, where Ringo Starr sings lead on the Fab Four’s rendition of Buck Owens’ “Act Naturally.” Owens, along with Merle Haggard, led country music’s West Coast vanguard in the 1960s with his acclaimed Bakersfield sound. With backing band the Buckaroos, Owens saw “Act Naturally” reach No. 53 on Hot Country Songs in 1963. On this tune, Owen sings sarcastically but sweetly about becoming a big movie star through his starring role in “a film about a man that’s sad and lonely,” since “all I gotta do is… act naturally.” And Ringo? He eventually dueted on the song with Owens in 1989. — THOM DUFFY

“Jackson” was originally released by the Kingston Trio in 1963, but when Johnny Cash and June Carter turned it into a duet four years later, they cranked the song’s charm and heat all the way up. With Cash’s deceptively crass demeanor and Carter’s sweet disposition, the song about a squabbling couple goes from a bit sad to a whole lot of fun. The song’s humor pops as Cash declares he’s gonna teach those Jackson women “what they don’t know how,” while it sounds like Carter’s got a movie-sized popcorn bucket out waiting to see him led “’round town like a scolded hound.” — T.M. 

“Freedom’s just another word for nothing left to lose,” sings Kristofferson in the unforgettable chorus of his masterfully penned “Me and Bobby McGee,” just one of the classic lyrics in this road song packed with exquisite lines. (“Feeling nearly faded as my jeans” purely defines melancholia). Those who know only Janis Joplin’s fiery blues-rock version, her posthumous No. 1 on the Hot 100 in 1971, must hear Kristofferson’s unvarnished, acoustic original. “If it sounds country man, that’s what it is,” he says to open his recording of the track. “It’s a country song.” — T.D.

“Lovesick Blues” became Hank Williams’ first No. 1 on the then-named Top Country & Western Singles chart, spending 16 weeks at the summit in 1949 and ultimately getting named Top Country & Western Record of the Year. Penned by Irving Mills and Cliff Friend, “Blues” was first performed by Anna Chandler in the Tin Pan Alley musical Oh! Ernest, and had been cut by other artists before Williams. A prolific songwriter, Williams rarely cut outside songs, but after performing “Blues” on the Louisiana Hayride with his inimitable yodel, the enthusiastic reaction led to him recording what ultimately became one of his signature songs. — D.E.P.

In January 1952, Hank Thompson went to No. 1 on Hot Country Songs with “Wild Side of Life,” in which he declared a certain woman would “never make a wife” because of her love of the nightlife. That summer, Kitty Wells slapped back with her debut single “It Wasn’t God Who Made Honky Tonk Angels,” a rejoinder aimed at unfaithful men everywhere, which topped the chart for six weeks. Ironically written by a man, J. D. “Jay” Miller, Wells’ signature hit nevertheless paved the way for declarations of empowerment and revenge — and chart success — from generations of female country singers who followed in her wake. — T.D.

From the way Patsy Cline draws out each word of the song’s titular phrase to the delicious melodrama of its lyrics, “I Fall to Pieces” isn’t just an all-time great country song; it’s also one of the best love songs of all time. A perennial country-pop standard, “Pieces” is so brilliant because of the way Cline’s ever-so-slight yodel colors her vibrato, making for a timbre that accentuates the track’s plucky piano line. A No. 12 Hot 100 hit, “Pieces” has lived many lives – from netting Trisha Yearwood and Aaron Neville a Grammy win in 1995 to being interpolated on Beyoncé’s historic Cowboy Carter LP in 2024. — K.D. 

Written by and first recorded by Jimmy Webb, this song would become the signature (and namesake) song of country supergroup The Highwaymen in the mid-1980s, rejuvenating the careers of the group’s members Johnny Cash, Willie Nelson, Kris Kristofferson and Waylon Jennings. The song centers on the reincarnation of someone living through multiple lifetimes, as a highwayman, a sailor, a dam builder and a starship flyer, with each member of the group giving voice and personality to a different role. The song earned a Grammy nomination for best country performance by a duo or group with vocal. — J.N.

This Alabama essential created an idyllic picture of old-fashioned rural living when it was released in 1982, with its visions of floating on down the river and spending the day being lazy feeling even more paradisiacal (and faraway) in today’s age of high-speed technology and attendant demands. A Hot Country Songs No. 1, the song also contains one of country music’s (or any music’s) best breakdowns, with its last 50 seconds being pure bluegrass hoedown, the very mountain music its lyrics so wistfully reminisce about. — K.B.

This catchy 1980 hit shows the influence that groups such as the Eagles had on music of that era that fused country, pop and rock. This was the biggest hit from the soundtrack to Roadie, which starred Meat Loaf as a truck driver who becomes a roadie for a traveling rock and roll show. This was the first of three consecutive Rabbitt singles that not only topped Hot Country Songs but also made the top five on the all-genre Billboard Hot 100. The windshield wipers so memorably referenced in the song resurfaced 10 years later in Rabbitt’s 1990 country hit “Running With the Wind,” which contained a sly reference to this earlier hit: “I listen to the windshield wipers go/ Just like the song I used to know/ I’m drivin’ my life away.” — P.G.

This enduring ballad of heartache and regret became a common concert opener for Twitty after he changed his sound in the ‘60s from rock and roll to country. The track’s two-word title was always spoken and not sung by Twitty, which, along with the wispy, tender tone and weeping guitars earned “Hello Darlin’” a No. 1 on Billboard’s Hot Country Singles chart in 1970. While Conway never revealed who he had written the song for, he regularly sang it directly to Loretta Lynn whenever the two performed together. — DAVE BROOKS

In her 1993 autobiography, Naomi Judd said she thought this song had “one of the strongest melodic hooks I’d ever heard.” Bandleader and guitarist Don Potter came up with the sharp-edged guitar licks, which Judd called “a little slice of heaven.” The song about yearning for love also features the duo’s impressive vocal gymnastics and gentle harmonies. In December 1984, this became The Judds’ second consecutive single to reach No. 1 on Hot Country Songs. This was the opening and title track on the duo’s first studio album. Brent Maher, who produced the album, co-wrote the song with Harlan Howard and Sonny Throckmorton. “Why Not Me” was named song of the year at the ACM Awards and single of the year at the CMA Awards. — P.G.

Recorded in 1927 and released the following year, “Blue Yodel No. 1 (T for Texas)” was the nascent country genre’s first smash hit, jumpstarting a national yodeling craze as well as the career of The Singing Brakeman’s Jimmie Rodgers, now recognized as the Father of Country Music. With a clean, open guitar tone that conjures up the wide plains of Texas and the smoky mountains of Tennessee, Rodgers captured the national imagination with high-pitched, mournful yodels that wordlessly punctuated each lyric of betrayal and anger in this blues-based song. Inspiring everyone from Johnny Cash to Howlin’ Wolf, this song’s themes – a cheating woman (“T for Thelma, that gal that made a wreck out of me”), a wounded ego and revenge at the point of a gun – reverberated through country for decades to come. — J. Lynch

Despite its glittery name, “Rhinestone Cowboy” is about a down-and-out singer, walking the streets of Broadway hoping to find his big break. It’s a beautiful country ballad brought to theatrical heights the next year by dazzling piano, soaring flutes and Campbell’s vivid vibrato as he sings “I’m gonna be where the lights are shinin’ on me.” With its robust sound and relatable lyrics, the song’s legacy has endured in the many covers (Campbell’s own 1975 version is a cover of the song originally written and performed by Larry Weiss a year earlier) performed over the years. Bruce Springsteen, Loretta Lynn, Charley Pride, Radiohead and Orville Peck have all taken their turn “riding out on a horse in a star-spangled rodeo like a rhinestone cowboy.” — T.M.

After Jackson finished his ode to young love and the Chattahoochee River, he wasn’t sure it would make his next album — much less become one of his most beloved hits. “I thought, if it’s on the record that’ll never be a single,” he told Apple Music in 2021. “No one else will understand what a Chattahoochee is.” To Jackson’s surprise, listeners were immediately drawn to the rollicking track, with its chugging guitar and flaring fiddle and lyrics about the joyous, idle days of youth spent returning to the riverbanks again and again learning “a lot about living and a little ‘bout love.” “Chattahoochee,” which became Jackson’s first Hot 100 hit, snagged both song and single of the year at the 1993 CMA Awards. — E.L.

Written by Country Music Hall of Fame songwriter Bob McDill, this literary song centers around a protagonist who makes his break from small-town Southern life after seeing how alcohol and drugs ravaged the lives of his friends and family. He learns “to talk like the man on the six o’clock news,” and distance himself from some markers of his rural heritage, while acknowledging that certain aspects, such as the love of the works of Hank Williams and Tennessee Williams, will always stay with him. “Gentle Giant” Williams’ laid-back baritone voice puts the song’s message across with ease. — J.N.

There are countless country songs likening women to liquor, but none are “as sweet as strawberry wine,” or rather, as Stapleton’s “Tennessee Whiskey,” from his 2015 debut solo album, Traveller. Stapleton describes the three drinks — Tennessee whiskey, strawberry wine and brandy – as smooth, sweet and warm, which are the exact elements listeners get from the song. The Southern rock guitar that pulls you in is smooth. The lyrics about how all he needs is the love of his woman are endlessly sweet and there are few things warmer in this world than Stapleton’s strong baritone at full volume. His medley of the Dean Dillon/Linda Hargrove-penned song with “Drink You Away,” performed with Justin Timberlake at the 2015 CMA Awards, was an epic, star-making turn. — T.M. 

Few songs released in the past 30 years can revitalize the energy of a room more quickly than the opening electro-country guitar riff of “Man! I Feel Like a Woman!” After all, there’s a reason it’s the greatest karaoke song ever — by the time that Twain’s honeyed “Let’s go, girls,” vocal hits, the party is already in full throttle. And why stop there? Take it from Twain: “Go totally crazy”; “really go wild.” It has the same level of no-holds-barred, feel-good fun today as it had in the late ‘90s. Have at it.  — JOSH GLICKSMAN

“I’m No Stranger to the Rain” reached No. 1 on the Hot Country Songs chart on April 8, 1989, and was Kentucky native Whitley’s final No. 1 prior to his untimely death in May 1989 due to alcohol poisoning. Though written by Sonny Curtis and Ron Hellard, Whitley’s rendering feels autobiographical, on lines such as “I’ve fought with the devil/Got down on his level/ But I never gave in.” The song endures for its distinctive theme, but also as a showcase for Whitley’s exceptional way of finessing a melancholy, lonesome lyric. — J.N.

There was little doubt about Underwood’s rising star status by the time she released “Before He Cheats” as a single in the summer of 2006 — but the menacing Some Hearts track cemented her as a top artist in the genre for years to come. Underwood spares no detail in her twangy recounting of her methodical revenge against an unfaithful partner’s car: those leather seats, headlights and tires are all goners, just like their love. Thankfully, she left the radio intact, where the song would get plenty of attention and become the second of her 16 Country Airplay No. 1s. — J.G.

Written in 1955 by Eddy Arnold and Cindy Walker, “You Don’t Know Me” entered the American lexicon as a masterful piece of songwriting, a tale of insecurity, anxiousness and unrequited love, woven into a grand, sweeping ballad. Ray Charles’ rendition, featured on his groundbreaking 1962 album, Modern Sounds in Country and Western Music, reached No. 2 on the Hot 100 and infuses the original with a soulful tone and notably melismatic approach that dances across the melody line. Despite the power in his belt and the way he traverses his range, Charles’ version of “You Don’t Know Me” is remarkably tender – the perfect complement to an arrangement that skews a bit more orchestral than Western. — K.D.

Willie Nelson was 27, the father of three, a struggling Nashville songwriter, signed to—and musing away an afternoon at — Hank Cochran’s music publishing company. “I just looked around and, for no reason at all, said `Hello walls,’” Nelson later recalled. An offbeat lyric emerged: “Hello walls/ How’d things go for you today?/ Don’t you miss her/ Since she up and walked away?” Faron Young, a smooth, established country hitmaker, recorded the song — which spent nine weeks at No. 1 on Hot Country Songs in 1961, and gave Nelson the then-biggest hit of his nascent songwriting career. — T.D.

Outlaw country typically houses some of the most raucous and fearless bits of its parent genre, and Willie Nelson and Waylon Jennings’ timeless cover of Ed Bruce’s classic is chief among them. A straightforward warning against the allure of the rough and rugged cowboy lifestyle, the Nelson-Jennings version of “Mammas” thrives because of the irony sewn into both artists’ vocal performances. With four weeks atop Hot Country Songs and a Grammy win for best country performance by a duo or group with vocal, “Mammas” was rightly a commercial and critical behemoth. — K.D.

The origins of Dolly Parton’s “I Will Always Love You” are so well-documented at this point that even casual fans of Billboard’s Greatest Country Artist of All Time know that she wrote the song as a goodbye to country legend and frequent collaborator Porter Wagoner. But that story and this song continue to resonate with every generation – including those who first heard it through Whitney Houston’s sensational 1992 cover for The Bodyguard – because of its unmatched heart. Parton’s powerful vocals mirror her bittersweet lyrics that acknowledge the fraught relationship, while still truly hoping life treats Wagoner kindly and wishing him well. It’s a perfect encapsulation of Parton herself: her ferocity and kindness combined for an evergreen track.  — T.M.

Despite all the very specific lyrical details about learning how to play guitar or having a favorite dog buried in the yard, this is about as universal a feeling as a song can capture. “House” proves that you can, in fact, go home again — and in the process, perhaps recapture a small piece of your formative years by treading the same floorboards you did growing up. The ultimate beauty of the Tom Douglas- and Allen Shamblin-written song is that, just like we all experienced so many formative experiences in our childhood homes, it also brought Lambert a lot of her own firsts — including her first Grammy (for best female country vocal performance) and her first Hot Country Songs No. 1. – K.A.

A four-minute ballad about suicide is hardly a tried-and-true recipe for commercial success, but Bobbie Gentry’s Southern Gothic slice-of-life took the nation’s breath away in 1967, topping the Hot 100 for four weeks and spurring decades-long debates over what the titular teen threw off the Tallahatchie Bridge before dying. A baby? A wedding ring? Gentry, the sole writer behind this harrowing first-person narrative, has always refused to elucidate, but one thing about the song is certain: Between the uneasy, stop-start guitar strumming, those disorienting swathes of strings and Gentry’s husky, cagey vocal, “Ode to Billie Joe” is an unsettlingly authentic portrayal of people casually shrugging off the suffering of others amid their daily routine. — J. Lynch

“The Race Is On” opens with a scene of romantic desolation. “I feel tears wellin’ up, cold and deep inside/ Like my heart’s sprung a big break,” Jones sings. “And a stab of loneliness sharp and painful/ That I may never shake.” But even as Jones’ narrator stares into the abyss, the instrumentation around him remains unwaveringly cheerful, a bright mash of jangly guitars and double blasts of percussion. This dissonance makes Jones’ despair as his relationship crumbles even more poignant, powering “The Race Is On” into the top five on the country chart — and even crossing over to crack the Hot 100, which was unusual for Jones in the 1960s. —E.L.

“Who doesn’t know what I’m talkin’ about?” Natalie Maines begins the Chicks’ most enduring single, then proceeds to describe the yearning for escape before gradually zooming in on one young woman loading up her car. Much like the Chicks are experts at balancing lyrical specificity with universal emotions, “Wide Open Spaces” masterfully props up a gargantuan chorus with production details — including banjo, mandolin, fiddle and organ flourishes — that still reveal themselves after dozens of listens. — J. Lipshutz

With a sparse opening of upright bass and snapping fingers keeping time, you may think you’re gearing up for a spoken-word performance from a 1950s beatnik. But then Roger Miller enters, his voice somewhere between a country artist and a lounge singer as he croons, “Trailers for sale or rent.” The train-hopping star of Miller’s tune might not have a lot going for him monetarily, but even as a “man of means, by no means,” he remains the “king of the road.” Rather than a rags-to-riches story, Miller’s song honors the idea of being happy with what you have, a concept that appealed to listeners of all stripes, as it hit No. 1 on Hot Country Singles, No. 4 on the Hot 100 and earned Miller a handful of Grammys at the 1966 ceremony. —  C.W.