The 200 Greatest Country Songs of All Time

Mainstream country’s most prominent liberal ambitiously overloads this nearly six-minute single from 2009’s American Saturday Night, explaining that he wanted “to serve up a little multigenerational truth with a strong sense of hope and possibility.” In this bright “Future,” Brad Paisley marvels at car DVD players and mobile-phone video games, imagines how trans-Pacific commerce might amaze his WWII vet grandfather and then brings his mid-tempo country-rocker down a notch to appreciate the racial progress that has occurred in his own lifetime — he debuted the song live at the White House. Basically, it’s a typical Brad Paisley ADD special, mixing synth lines with steel guitar, fiddle breaks with speed riffs, and sense with sentiment. —R.G.

Stoney Edwards was among the Black artists signed after Charley Pride cracked the country industry color line. Edwards’ “Hank and Lefty Raised My Country Soul,” about growing up a fan of genre forefathers, is a frustrating reminder of how those singers were often required to foreground their country bona fides in ways white acts mostly were not. It’s also one hell of a record. The arrangement may savvily meld the sounds of both Williams’ Drifting Cowboys and Frizzell’s Western Cherokees, but Edwards’ warm Oklahoma twang is nobody’s but his own. And the story Stoney’s telling — embracing his old man’s musical heroes instead of rebelling against them the way a rocker might — is the embodiment of country tradition. —D.C.

The Seventies were a time of country power couples, from George Jones and Tammy Wynette to Johnny Cash and June Carter Cash. But the best of all weren’t even a couple: Loretta Lynn and Conway Twitty. They kicked off their collaboration with five straight Number Ones early in the decade, and they were still steady hitmakers by the time they delivered their weirdest, and funniest, entry in the canon. A funky toe-tapper that lopes along at a comedic pace, “You’re the Reason Our Kids Are Ugly” doesn’t take itself seriously for one second, but Lynn and Twitty are fully committed as they rattle off examples of how poorly the other has aged and contaminated the gene pool. —J. Gage

Originally a collective of Nashville outcasts and outsiders known for their open-minded open mic night, the MuzikMafia went mainstream with the twin successes of Big & Rich’s “Save a Horse (Ride a Cowboy)” and Gretchen Wilson’s “Redneck Woman.” With its upbeat swing and beer-drinking, Walmart-wearing identity politics, “Redneck Woman” quickly rose up the country chart. Following a breakthrough performance at the 2004 Country Radio Seminar, “Redneck Woman” became the fastest-rising Number One since Billy Ray Cyrus’ “Achy Breaky Heart.” Though Wilson herself was never able to repeat its success, the song paved the way for rocking female badasses like Miranda Lambert and Kimberly Perry. —N.M.

According to Bill C. Malone and Tracy W. Laird’s book Country Music U.S.A., Gene Autry “completed the ‘romantic westernizing’ begun by [Roy] Rogers,” and in fact, Autry’s early singing career was mostly as a performer of Rogers’ songs. But Autry had his own easy charm that translated to the big screen and record sales alike. Autry had been a star for years by the time “Back in the Saddle” came around — a last-second addition to the movie Border G-Man (1938), commissioned after songwriter Ray Whitley got a 5 a.m. call requesting another song by 8 a.m. “Well, I’m back in the saddle again,” he told his wife after she asked who’d called. “Well, you’ve got a good title,” she responded. Autry recorded it numerous times — the first, in 1939, was his second gold record — and turned it into his theme song, as well as the title of his autobiography. —M.M.

Brandi Carlile’s best song is an oversized anthem with one of the greatest vocal performances in 21st-century country music. It stirringly invokes the voices of marginalized and minority groups who felt new levels of terror during the Donald Trump years, with Carlile’s wail soaring above producers David Cobb and Shooter Jennings’ empathetic production to embody all the pain, anger, and desperation of that era. “The Joke” became an instant showstopper, netting Carlile a pair of well-deserved Grammys. It would no doubt be a standard by now, too, except that it’s impossible to imagine any others singer driving it home with the same power as the woman who wrote it. —J. Gage

Instead of moving to Nashville and playing bars until he got a break, Zach Bryan joined the Navy and used his off-hours in his barracks to write songs and post them on YouTube, before independently releasing two albums while in active service. After an honorable discharge and a major-label deal, Bryan released “Something in the Orange” as the first single off his 2022 album, American Heartbreak. Bryan doubles down on what made him special: simple instrumentation that leaves room for his poetic lyrics sung in an urgent plainspoken voice. Bryan proved that unadorned authenticity could fill arenas in the 2020s, and it made him one of the biggest acts of any genre. —B.S.

The Oak Ridge Boys got their start in the 1940s, when they came out of Knoxville, Tennessee, singing gospel as the Oak Ridge Quintet, and they kept the classic vocal group tradition alive when they went country in the slick 1970s and 1980s. The Oaks’ casual-sharp look and equally pliant musical outlook made their crossover moves feel easy, including appearances on other artists’ tunes (like their beautiful low-key turn on Paul Simon’s “Slip Slidin’ Away”). Their biggest pop moment was “Elvira,” with its jovial gait, horn section, and fun-to-sing hook “Giddy up, um-poppa-um-poppa, mow, mow,” delivered by well-deep bass singer and Camden, New Jersey, native Richard Sterban. —J.D.

Released in February 2024 but already a game changer, Beyoncé’s “Texas Hold ‘Em” became the first record by a Black woman ever to debut atop the Billboard Hot Country Songs chart. Will it prove consequential in other ways, too, helping at long last to integrate country radio? Will it inspire a line-dance revival or spark a traditionalist backlash? Maybe all of the above? We’ll see. What we know already is that from Rhiannon Giddens’ opening banjo lick to that bareback Western beat and on through to those fife-and-drum-suggesting whistle breakdowns, this “real-life boogie and … hoedown” is a 21st century country banger of the highest order. —D.C.

The first country star of Mexican-American descent, Johnny Rodriguez demonstrated the fluidity of the genre by singing his recordings in English and Spanish. “You have stories in Mexican music, and country music said almost the same thing, just in different languages,” he said in Ken Burns’ Country Music documentary. His 1973 single “Ridin’ My Thumb to Mexico” was a story all right, a weeper penned by Rodriguez alone about disappearing into another country when the world’s got you down — the forlornness in his voice almost at odds with the lushness of Jerry Kennedy’s production. It went on to become his second Number One hit, one of several Rodriguez charted in the Seventies. —J.F.

Songwriter Guy Clark thought of his snappy-tempoed “Heartbroke” as something akin to a Chuck Berry tune. When Ricky Skaggs cut it for his groundbreaking 1982 bluegrass-country album, Highways & Heartaches, the future Country Music Hall of Famer admitted he didn’t really understand what the song was about. Still, he knew how to sell it. The first of three singles from that LP to top the country chart, “Heartbroke” simultaneously proved popular with other acts, including an up-and-coming George Strait. But it was Kentucky native Skaggs who delivered the liveliest take on the tune, making a slightly sanitized tweak to Clark’s line, “pride is a bitch and a bore when you’re lonely,” but diminishing none of the song’s effusive delight. —S.B.

Born in Arkansas and raised in Los Angeles, Iris DeMent has a voice with a vibrato-infused twang that purrs and bucks, and her songcraft has always remained full of heart and earthly spirituality. This song, which opened her outstanding 1993 debut, Infamous Angel, is an object lesson, weighing ideas about heaven, purgatory, and the afterlife, then sensibly throwing up her hands: “No one knows for certain and so it’s all the same to me/I think I’ll just let the mystery be.” It launched a marvelously unconventional career that’s veered from gospel standards to protest songs to an LP inspired by Russian poet Anna Akhmatova (The Trackless Woods). “Let the Mystery Be” would become a standard of its own; one recent cover was delivered by Wilco’s Jeff Tweedy on his Starship Casual Substack. —W.H.

With heart-tugging songs about his wife and kids, Luke Combs quietly evolved into country music’s leading family man during the 2020s — but damn if he couldn’t still write an excellent drinking song too. “Beer Never Broke My Heart,” released in 2019, is right up there in country’s frosty canon, thanks to Combs’ clever, relatable lyrics and his husky delivery. The way he emphasizes every phrase of the chorus with a heavy pause — “Long neck! Ice cold! Beer never broke my heart!” — has enough singalong power to make you run through a wall. And his soulful approach to the bridge (“It takes one hand to count the things I can count on”) is proof that Combs can’t help but add real emotion to every line he sings. —J.H.

Turnpike Troubadours have been leaders in the revival of Red Dirt country, an Oklahoma sound that goes back to the mid-20th century. It follows that “The Bird Hunters,” one of the best songs to come out of that tradition, is about going home to East Oklahoma. “The Bird Hunters” perfectly marries traditional storytelling and traditional instrumentation, with a modern Southern rock feel. But it’s Evan Felker’s story that makes the song hit so hard — about a guy trying to figure out his life after a move to Tulsa doesn’t work out, and the friend and the dog that help remember who he is. It’s a story you’ve heard many times, but the Troubadours tell it with detail and heart few other bands can match. —B.S.

One night in the late Seventies, Eagles manager Irving Azoff approached Johnny Lee, who led the house band at the Houston bar Gilley’s, and asked him if he wanted to sing in a movie Azoff was involved in as music coordinator. “Well, people were bullshitting me all the time,” Lee later told Texas Monthly. “So I said, ‘Yeah, sure, just as soon as I finish this watermelon. You bet.’” The bet paid off handsomely: Urban Cowboy, starring John Travolta and Debra Winger, was a box-office hit, and so was the soundtrack, led by a mellow Lee-crooned singles-bar anthem, “Lookin’ for Love,” which Gilley and another music coordinator had found in a pile of demos. “I couldn’t believe I hadn’t written it myself,” Lee said, “it was the story of my life up till then.” —M.M.

Keith Urban’s 2002 album, Golden Road, cemented his status as a wildly talented superstar with crossover potential. On the last and finest of that album’s four singles, the guitar-shredding Aussie reached for his acoustic and picked out an exquisitely bitter breakup ballad. “Take your records, take your freedom/take your memories, I don’t need ‘em,” he sings, doing his best to move on, but it’s clear from Urban’s mournful tone that he’s lashing out because he’s also in pain. Released as a single in 2004, the song went to Number One and crossed over to the adult contemporary and adult top 40, eventually earning Urban his first Grammy award. —J.F. 

Old Crow Medicine Show’s “Wagon Wheel” was around for over 30 years before the band recorded it, and it existed for another 10 years before it became a hit. The song began as an untitled, unfinished Bob Dylan song from the 1973 Pat Garrett and Billy the Kid soundtrack sessions. Old Crow Medicine Show cut a fiddle-driven version of it in 2004, adding their own lyrics in place of Dylan’s mumbled vocal. Nine years later, Darius Rucker went to Number One on the Billboard Hot Country Songs chart with his warm take on the tune. “We’ve never met Dylan,” Old Crow’s Critter Fuqua noted, “but the song is technically co-written by Bob Dylan.” —J.D.

No artist made more appearances on country radio’s influential WSM Barn Dance than “harmonica wizard” DeFord Bailey. Bedridden with polio as a youth, Bailey absorbed the sounds of his native Tennessee — the chugging and whistling of trains, the howling of hound dogs, the shouts of fox hunters, the cackling of hens — and would conjure them on his harp. Named for the train that made the trek between New Orleans and Cincinnati, “Pan-American Blues” was a three-minute piece of locomotive cinema worthy of the Lumière brothers. One of country music’s first Black stars, Bailey was also one of the biggest early stars of a popular new radio show called The Grand Ole Opry. —C.W.

Sometime in the mid-Nineties, Dierks Bentley and his father drove an aging Chevrolet pickup across the country from Arizona to Nashville. In 2012, by which point Bentley had become a star, his father died. You don’t necessarily need that context to appreciate his sturdy, determined 2013 single “I Hold On,” but knowing it makes that first verse about why he’s still driving that pickup truck hit so much harder. The song would appear on Bentley’s seventh album, Riser, a landmark release that stands as one of his best. And though he’s not been afforded the same rapid rise as some of his stadium-filling peers, songs like this one demonstrate that Bentley’s going to be around long after those other stars fade. —J.F.

Early records by Sons of the Pioneers — the vocal group led by Roy Rogers before becoming Hollywood’s “King of the Cowboys” alongside his wife and co-star, Dale Evans — had an unearthly quality, thanks to Rogers’ stirring vocal interplay with Bob Nolan and Tim Spencer. Recorded during the Sons’ first recording session, “Tumbling Tumbleweeds” conjures wide-open skies with its arcing harmonies and generous violin, but the lyric’s swooning quality belies its era: this strangely sanguine song about the joys of vagrancy hit during the depths of the Great Depression. Nonetheless, it’s also droll — as they travel, the tumbleweeds of the title are “pledging their love to the ground.” —M.M.

The signature song of Southern gothic panorama painter Mary Gauthier is a plea for compassion that eases from personal to the universal and back, an existential cry that requests “mercy now” for her dying father, our struggling empire, our fragile planet and, finally, ourselves. She began writing the song after visiting her father, hospitalized with Alzheimer’s-like symptoms after a car accident. Inspired by the repeating lines of Lucinda Williams’ 1988 song “Changed the Locks” and the evolving landscape of post-9/11 America, she decided to, in her words, “back the camera up.” Years later Rolling Stone would dub “Mercy Now” one of the 40 Saddest Country Songs of All Time. “I’m honored,” Gauthier said, “but ‘Mercy Now’ is not sad, it’s real.” —C.W.

Tammy Wynette once described Vern Gosdin as “the only other singer who can hold a candle to George Jones.” The country traditionalist’s most affecting hit single, and the 1989 CMA Song of the Year, certainly confirms that status. Co-written by Gosdin with Max D. Barnes, “Chiseled in Stone” is a classic barroom ballad in which casual conversation turns to deep reflection, then to unrelenting heartache. Gosdin’s supreme gift was in being able to convey each of those emotional stages with equal gravitas, never once inching toward mawkishness, even as it’s clear he’s talking with someone whose devastating life experience will make his own pale in comparison. —S.B.      

The 2020 police murder of George Floyd sent shockwaves through America, even the often right-leaning world of country music. Few artists in any genre grappled with racism in America as powerfully as Tyler Childers did on this title track of his third studio album, a primarily instrumental record of public domain fiddle tunes that builds to a powerful message. On the album’s closer, “Long Violent History,” the only song on the LP with lyrics, Childers does not mince words. Considering his place as “a white boy from Hickman,” he invites listeners to consider how they’d feel if they were “just constantly worryin’/Kickin’ and fightin’, beggin’ to breathe.” Childers released the song with an accompanying video message, in which, among other heartbroken declarations, he wishes for “justice for Breonna Taylor, a Kentuckian,” like Childers himself. —B.M.

Pam Tillis was one of the most luminous stars of the 1990s country boom, with her unique mix of twang, sass, and soul. It’s in her blood: Her dad, Mel Tillis, was a Nashville legend, with classic hits like “Midnight, the Blues, and Me.” (She sang backup on his 1980 hit “Your Body Is an Outlaw.”) After a spell singing New Wave pop in the Eighties, she blew up into a country star with her 1991 signature song “Maybe It Was Memphis,” a steamy ballad recalling summer romance with a boy straight out of a Faulkner novel. Her iconic hits include “Put Yourself in My Place,” “Spilled Perfume,” “Mi Vida Loca (My Crazy Life),” and her Egypotological honky-tonk lament, “Cleopatra, Queen of Denial.” —R.S.

Through most of its history, country music was identified as grown-up music. Kathy Mattea, a warm-voiced singer who helped keep folkie-pop country alive on the radio in the decade between Anne Murray and Mary Chapin Carpenter, landed the biggest hit of her career with “Eighteen Wheels and a Dozen Roses.” Charlie, a trucker who’s finally retiring, is headed home to his wife with a plan to trade in his big rig for an RV and plenty of free time. “With pieces of the old dream, they’re gonna light the old flame,” Mattea sings sympathetically and without a hint of condescension. “Doin’ what they please.” Life begins at retirement. —D.C.

There are plenty of self-described outlaw country artists with rap sheets shorter than a goldfish’s memory, but bluegrass artist Billy Strings slings real-deal, law-breaking truth on “Dust in a Baggie,” a 2013 collaboration with then-musical partner Don Julin. Strings and his parents became addicted to methamphetamine when the guitar virtuoso was a pre-teen, a struggle loosely and humorously documented in this tune. Along with some furious picking, it’s anchored by one of the finest, catchiest chorus couplets in country music: “I used my only phone call to contact my Daddy, I got 20 long years for some dust in a baggie.” Fortunately, Strings himself didn’t land in lockup, instead finding and maintaining the California brand of sobriety. —B.M.

It wasn’t a given that Darius Rucker would enjoy success as a country artist, despite Hootie & the Blowfish influencing an entire generation with their melodic brand of folk rock. But Rucker’s 2008 solo debut was an undeniable winner — a grown-up country anthem that demonstrated how so many of us will get to experience some version of “what if things had been different?” years after an old breakup. “Don’t Think I Don’t Think About It” hit Number One on the country chart, making Rucker, who co-wrote the song, the first Black artist to hit Number One since Ray Charles duetted with Willie Nelson on “Seven Spanish Angels” in 1985. —J.F.

George Jones once deemed it the most perfect song ever written, and along with “Happy Birthday to You” and “White Christmas,” it is considered one of the world’s best known. While hundreds of versions of the song exist, the most beloved remains the original 1940 recording by Jimmie Davis. With an unverified authorship as complicated as its forlorn lyrics, “Sunshine” is hardly as sunny as its title implies. Davis’ own story is equally complex; he led one of the first racially integrated bands in country music history, but later ran on a segregationist platform as two-term governor of Louisiana. The popularity of “You Are My Sunshine” has remained entirely colorblind, however, with hit versions by everyone from Bing Crosby to Aretha Franklin. —S.B. 

“Can we change ‘Austin’ to ‘Boston’?” Jo Dee Messina asked songwriters Tim Nichols and Mark Sanders before recording this last-minute addition to her debut album. “‘Cause I really do have people in Boston!” Born in Framingham, Massachusetts, Messina spent her first years in Nashville tending bar and entering talent contests. “Heads Carolina, Tails California” made her a star, its lyrics marking a permanent shift in country music’s geography. Earlier in the 20th century, California and the Carolinas had been hubs of country production. For Messina, as for countless listeners who found the genre during its Nineties explosion, they were destinations, promised lands of sunshine and twang. —N.M.

“I hate that album,” Linda Ronstadt told Rolling Stone in reference to her 1970 country LP Silk Purse. “I couldn’t sing then; I didn’t know what I was doing.” But for Ronstadt, one track was an exception: “Long Long Time.” Written by Gary White, it’s a heart-shattering tale of unrequited love that showcases her incredible vocal range. Listeners had already heard Ronstadt’s enchanting cover of Michael Nesmith’s “Different Drum” with the Stone Poneys, but “Long Long Time” became the proper introduction to her powerhouse vocals. It was her first solo single to chart, and it earned Ronstadt her first Grammy nomination. In 2023, more than five decades after its release, the song’s appearance on HBO’s The Last of Us brought it back into public consciousness. —A.M.

Country music loves a story about a plucky underdog who wins in the end. In the case of Sugarland’s 2004 debut, “Baby Girl,” it’s actually a story about making it in country music. With its bright, clean melody and crisp, three-part harmonies, the song’s chorus reads like a letter (or maybe email) asking the folks back home for money, but Jennifer Nettles, Kristian Bush, Kristen Hall, and co-writer Troy Bieser also wove some pointed criticism of the cutthroat music industry through the verses. “Big town full of little white lies/Everybody’s your friend, you can never be sure,” Nettles sang. “Baby Girl” served as a worthy introduction to multi-hyphenate star Nettles and predicted one path in country music that echoed on through Carrie Underwood, Kelsea Ballerini, and, yep, Taylor Swift too. —J.F.

At first glance, “Drink a Beer” looked like another tailgate song from the onetime king of spring break. Instead, the ballad guts listeners with its tale of paying tribute to someone gone too soon. Bryan sells it all with tragic experience — both his brother and sister died young — and his lingering grief is the throughline of the song, written by Chris Stapleton and Jim Beavers. Bryan’s performance of “Drink a Beer” at the 2013 CMA Awards (with a still-unknown Stapleton singing behind him) ripples with raw emotion. But it’s the studio version that stands as Bryan’s high-water mark, a moment of rare, palpable sorrow from one of the genre’s most happy-go-lucky artists. —J.H.

Brenda Lee, the first woman to be inducted into the country and rock and roll halls of fame, was only 15 when she cut “I’m Sorry” with producer Owen Bradley, the Anita Kerr Singers, and studio pros the A-Team. A pop Number One that never cracked the country countdown, “I’m Sorry” is today both a paragon of the Nashville sound and another reminder that genres are largely arbitrary concepts. The record is a mystery in so many ways. For starters, how did Lee manage such depths of emotional prostration when she was still so very young? She apologizes over and over, keeps begging for forgiveness. What exactly did she do? Will she ever forgive herself? —D.C.

The recipe for a great country song? Hang out with your friends on a porch and pass around a bottle of Bulleit Rye. Margo Price wrote “Hurtin’” one evening with her husband, Jeremy Ivey, along with Caitlin Rose and Mark Fredson, and released it on her 2016 debut, Midwest Farmer’s Daughter. It’s still her most popular song, because who doesn’t love a swinging anthem about whiskey and heartbreak? Though Price has since quit alcohol, she doesn’t mind performing “Hurtin’ (on the Bottle).” In fact, she welcomes it. As she told Rolling Stone last year. “Jeremy was like, ‘You don’t even drink anymore. Do you want to play any drinking song? Do you even think that that connects with you?’ I was like, ‘It fucking resonates with me now more than ever.’” —A.M.

Brandy Clark was already an A-list Nashville writer (see Miranda Lambert’s “Mama’s Broken Heart,” et al.) when “Pray to Jesus,” the opening scene of Clark’s solo debut, 12 Stories, introduced a singer-songwriter of consequence. Delivered in first person on behalf of folks who “pray to Jesus” and “play the lotto” because “there ain’t but two ways/We can change tomorrow,” it’s a character study that might sound a bit condescending until the details accrue, and you feel its knowing empathy. Clark’s easy way with wordplay — funny, wise, poignant, and pained — has taken her and frequent co-writer Shane McAnally all the way to Broadway, via their work on the musical Shucked. —W.H.

Though Louisiana-born Tony Joe White begins by defining “polk salad” for anyone who may have “never been down South too much,” and spends most of his time telling tales about the title character’s chain-gang-working mama, no-count dad, and alligator-eaten granny (“chomp, chomp”), this is first and foremost a love song — just check out White’s horny grunts, randy guitar licks, and sweaty groove as he remembers wild child Annie. Cut with the original Muscle Shoals rhythm section, years after they’d transplanted to Nashville for session work, “Polk Salad Annie” was an early example of a rootsy subgenre that became known as country funk. Decades later, it remains the country funkiest. —D.C.

Wanda Jackson sang with her own feral growl, aggressively sexual, a danger girl born to raise hell. The Oklahoma firecracker earned her Fifties crown as the Queen of Rockabilly. Discovered by her idol Hank Thompson, touring with her boy Elvis Presley, Jackson banged out a string of libidinally crazed tunes like “Fujiiyama Mama,” “Funnel of Love,” and “Tongue Tied.” But her ultimate classic is the 1956 single “Hot Dog! That Made Him Mad,” the feminist guitar anthem where Jackson raves about the erotic thrills of tormenting the menfolk. She defined the rebel spirit of female rockabilly pioneers like Janis Martin and the Collins Kids. In later years, Jackson turned to gospel (“Jesus Put a Yodel in My Soul”), but she teamed up with fan Jack White for her superbly unrepentant 2011 comeback, The Party Ain’t Over. —R.S.

Hank Snow sings “I’m Moving On” with his characteristically nasal and hyper-enunciated twang. He says he’s catching a train back south as fast as he can to escape the “pretty mama” who did this “true-loving daddy” wrong. It’s a good bet, though, that the reason his song remained perched atop the country chart for a ridiculous 21 weeks is his band’s headlong rhythm — its train-track sway, lonesome-whistle steel guitar, and his own hot flat-picked lead. “I’m Movin’ On” was state-of-the art country & western in the middle of the last century, and here in our new one, Snow’s record still sounds like it’s gaining steam. —D.C.

This 2010 breakout from the Band Perry’s self-titled debut album goes right past the idea of living fast and goes straight to dying young. Written by lead singer Kimberly Perry, “If I Die Young” remains peerless in its heart-wrenching portrayal of a life taken too soon, turning on the almost too-vivid image of “the sharp knife of a short life.” Certified seven-times platinum, the song remains the sibling trio’s biggest hit and has had a pop culture life of its own — featured prominently on American Idol (famously performed during Season 10 by Lauren Alaina) and Glee, on which it was covered by the late Naya Rivera in honor of castmate Cory Monteith, who died at age 31 in 2013. Rivera notably died young, too, passing away at age 33 in 2020, at which point the song saw a resurgence in popularity. —B.M.

Before there was “White Line Fever,” “Convoy,” or “East Bound and Down,” there was “Six Days on the Road,” the song that forever hitched country’s hard-working, blue-collar image to the trailer of a semitruck. While not the first trucking song by any stretch of highway, “Six Days” was an early hit that masterfully captured the loneliness, monotony, demands, and minutiae of truck life. “I think it was one of those songs that truck drivers in those days were waiting for,” Dave Dudley told the authors of The All-American Truck Stop Cookbook. “They were kind of like outlaws back then. After that song came out, I got letters from those guys saying thank you for taking the load off our back. It kind of helped change their image to knights of the road.” —C.W.

Of all the places to write “the perfect country & western song,” per this tune’s own lyrics, it’s hard to think of anywhere more unlikely than Paul Anka’s personal suite at the Waldorf Astoria. Yet that’s where Steve Goodman and John Prine first put pen to paper on this parody/celebration of country music cliches. “I was feeling pretty good,” said Prine, referring to a successful raid of Anka’s liquor cabinet, “so I jumped up on the bed and acted like I had an imaginary fiddle and said, ‘But you don’t have to call me darlin’, darlin’.” Most artists would have run from the song’s cheekiness. David Allan Coe, however, played it up, adding a bridge in which Goodman himself appears as a character, intentionally writing more clichés into the lyrics. —N.M.

Billboard had a good phrase to describe the Mavericks’ position vis-a-vis the mid-Nineties Nashville firmament: “unorthodox but platinum.” Their biggest hit on the Billboard country chart — reaching Number 13 in 1996 — is an irresistibly spry Tex-Mex groover: organ spritz on the two and the four, insistent shakers and hi-hats throughout, Raul Malo’s handsomely husky tenor having the time of its life. All of it is a setup for Flaco Jiménez’s accordion, constantly commenting on the action, assuming a comfortable place in front of the music whenever it flickers into earshot. —M.M.

This dreamy, swooning lovers conversation was the biggest vocal hit of 1960. A classic of the early Nashville sound, the vibraphone-heavy waltz intentionally mirrored the arrangement released earlier in the year by rockabilly performer Billy Brown. However, it was the deep, velvet-smooth baritone of Gentleman Jim Reeves that took the song over the top. “I can’t really tell you what the reason for that tune’s popularity was, except that I get the very pathetic picture of the old fellow standing in the telephone booth, about half plastered, talking with his girl, asking her to run the other guy off,” Reeves said. “Makes for pretty good listening though, I guess.” —C.W. 

A newlywed couple has their first fight, so the man takes off to a bar. But instead of getting hammered and commiserating with his bartender, he gets served a glass of milk. Chesney applies multiple meanings to the title: “The Good Stuff” could be a stiff drink, but it also signifies meaningful moments in life. By the end, it’s revealed the bartender lost his wife to cancer, and the memory of her is stronger than anything whiskey can offer. Songwriters Craig Wiseman and Jim Collins wrote the track after their friend lost his spouse to illness. “We were talking about, what if you just sat there and watched your wife die?” Wiseman later recalled. “We both just sat there and were sort of stunned for a minute. We said, ‘OK, let’s get a cup of coffee and write a song!’” —A.M. 

This wasn’t country’s earliest adaptation of disco’s patented boom-swish beat, but aside from Dolly Parton’s “Nine to Five,” it may have been the era’s canniest, with drummer Hayward Bishop utilizing those club-ready accents while sticking resolutely with a bouncy two-step rhythm. The track floats like Philly soul (the strings are more Barry White than Billy Sherrill) while remaining resolutely Nashville — but the song itself came from Memphis, a 1972 soul hit on Stax Records for Luther Ingram. Barbara Mandrell, eight albums in and ready for the big stage, took this pained, guilt-ridden, overwhelmingly horny lyric and delivered a showstopper, at once subtle and inflamed. It was her peak crossover moment, reaching the Billboard pop Top 40, her only appearance there. —M.M.

There was a time, not so long ago, when combining country and hip-hop was considered blasphemous, problematic, gauche, and maybe even avant garde too. “Cruise” was all of this and more, a high-summer love song in which trucks, girls, and the FGL boys themselves all take turns as objects of affection. Like a few of the other records on this list, it initially was accused of ruining country music. (“There’s no label that can really hurt our feelings,” FGL’s Brian Kelley said when asked about “bro country” on 60 Minutes.) A decade later, however, the twangy banjo that plays during the verses almost sounds old-fashioned — just as the jacked-up Silverado in the music video almost looks small. —N.M.

Mickey Guyton delights in country music tradition; she happens to be a Black woman, and she mapped out her experience in this breakthrough ballad. “If you think we live in the land of the free/You should try to be black like me,” she sang over pedal-steel cries on the track, teasing out the strands of R&B and Black church music so integral to country’s 21st century DNA. The song sat on her shelf until the murders of Ahmaud Aubrey and George Floyd spurred her to post fragments of it to social media. The response was swift, and within a year, she’d perform it on the Grammys — remarkably, shockingly, the first Black woman ever nominated for Best Country Solo Performance. Guyton didn’t win. But her song changed the dialogue around Black country artists, and it helped open doors for a generation of new voices. —W.H.

Emmylou Harris was on the cusp of stardom and one of the most in-demand singers in Nashville when she released her sophomore album, Pieces of the Sky, in 1975, but she was weighed down by grief. Her singing partner, mentor, and close friend Gram Parsons had died a little over a year before from a drug overdose. Harris channeled that heartache into what became her signature song. “Words can be so powerful to help you express something you can’t otherwise,” she said years later. “And everyone has experienced loss.” Few people, however, could make it sound so beautiful, a raw confession of sorrow illuminated by her shimmering soprano, destined to be one of the most unmistakable voices in country music. —J. Gage

The Oklahoma singer Joe Diffie sang the ultimate small-town romance in “John Deere Green,” from the legendary songwriter Dennis Linde. It’s a gem of country storytelling, where Billy Bob declares his love for Charlene by painting their names inside a 10-foot heart on the water tower. The tractor-themed color is the detail that clinches it, with the hook, “The whole town said that he should’ve used red/But it looked good to Charlene, in John Deere green.” In March 2020, Diffie tragically became one of music’s first victims of the Covid-19 pandemic, only 61, but he left a lifetime’s worth of classics like “Honky Tonk Attitude,” “Pickup Man,” and “Bigger Than the Beatles.” —R.S.

Conway Twitty was a rock and roller who in the Sixties and Seventies helped transition Elvis Presley-styled balladry into the country mainstream and who sang about sex as frankly and routinely as any country singer before him. “You’ve Never Been This Far Before,” where Twitty purrs that his “trembling fingers touch forbidden places,” was even boycotted, if only briefly, by a few major stations. What makes this record work is how understated, even naked, it all sounds — the only instrument that registers most of the way is throbbing electric bass — and the way Twitty’s repeated “buh-buh-buh” doubles as heartbeat and hook. —D.C.