The Best 90s Country Songs

Lorrie Morgan - Except for Monday

“Except for Monday, which was never good anyway / Tuesday, I get a little sideways / Wednesday, I feel better, just for spite / Thursday and Friday take too long / Before I know it, Saturday's gone / But it's Sunday now and you can bet that I'm alright…”

‘Except for Monday’ is not only essential Lorrie Morgan, the plucky sing-a-long is quintessential ‘90s country.

The 1991 ditty, which was penned by Reed Nielsen, became a smash hit for the oft-overlooked star. Released as the third single of Morgan’s Something in Red release, ‘Except for Monday’ peaked at No. 4 on the Hot Country Songs chart in the United States and went on to invade the Canadian airwaves, hitting No. 7 on their country rankings.

‘Except for Monday’ and Lorrie Morgan have come to be known hand-in-hand, the bop inseparable from its singer. The tune is still one of the artist’s top offerings, having garnered tens of millions of streams across platforms today.

- Alli Patton

George Strait - Love Without End, Amen

Released in the spring of 1990 as the lead single from Livin' It Up, 'Love Without End Amen' went on to become George Strait's biggest ever hit. Quite the feat in a decade when King George sat firmly on his country throne.

Strait has recorded some of the best songs about the trials and tribulations of fatherhood through the years – 'The Best Day' and 'So Much Like My Dad' among them – and likewise 'Love Without End Amen' has gone on to be a fixture on Father's Day playlists ever since.

The Texan recalls being sent home from school for fighting and, expecting to be punished, upon telling his father what happened was surprised by his dad reminding him that a parent's love is unconditional and "without end."

When Strait has a son of his own later in life, he is reminded of his father's laissez-faire approach to parenting, and in the final verse, dreams of dying as his father's words come back to him again at the pearly gates. By this point, if you're not a blubbering mess then there's something seriously wrong with you.

Some studies do show that without discipline, children may struggle to understand boundaries and acceptable behaviour, have poor socials skills and commitment issues.

Maybe that's why the cowboy is always riding away.

- Jof Owen

Reba McEntire and Linda Davis - Does He Love You

Reba McEntire has had many an iconic country song throughout her career, songs like the fierce ‘Fancy,’ spunky ‘Little Rock,’ empowering ‘I’m A Survivor’ and heart-wrenching ‘Whoever’s In New England’ coming to mind almost instantly.

Yet, one of the most legendary songs from her glowing discography lies in one of the tunes that, honestly, never should’ve happened… at least not the way it did.

‘Does He Love You,’ the first single from her 1993 Greatest Hits Volume 2 record, was written over a decade earlier by Billy Stritch and Sandy Knox and pitched to heavy hitters Barbara Mandrell and Liza Minnelli before ending up in McEntire’s capable hands. While being pushed to record the duet with more established acts of the time like Wynonna Judd or Trisha Yearwood, the Oklahoman instead opted for her then background singer, Linda Davis, to step in and add her chilling vocals to the tune.

Depicting the messy story of a love triangle gone wrong, much in the same vein of Carly Pierce & Ashley McBryde’s ‘Never Wanted To Be That Girl,’ the song struck a chord, winning the Grammy for Best Country Vocal Collaboration and Vocal Event of the Year at the CMA Awards.

- Lydia Farthing

Kenny Chesney - How Forever Feels

Penned by Wendell Mobley and Tony Mullins, this late ‘90s classic served as a turning point in Kenny Chesney’s career.

With the iconic lyric “Oh, now I know how Jimmy Buffet feels” and a music video that introduced Chesney to the US Virgin Islands for the first time, ‘How Forever Feels’ laid the foundation for a transition away from a steel-soaked, George Strait-inspired sound and towards his now-signature brand of Tropical Country.

Surging to No. 1 on Billboard’s Hot Country Songs chart and reaching the Top 30 on the all-genre Hot 100, ‘How Forever Feels’ finds Chesney at his playful, glass-half-full best, delivering each line with a twinkle in his eye, as a galvanising, fiddle-backed instrumental keeps the momentum high throughout.

The song gave the country music world their strongest indicator yet that Chesney was destined to become one of the genre’s biggest stars of the 2000s.

- Maxim Mower

Tanya Tucker - Two Sparrows in a Hurricane

Tanya Tucker returned to dynamic form on 1992’s well executed Can’t Run From Yourself.

Her 20th album produced three Top 10 Billboard Country Singles, and while ‘It’s A Little Two Late’ and ‘Tell Me About It’ embodied her known lighthearted sexiness, it was the tender ballad ‘Two Sparrows in a Hurricane’ that resonated while showcasing the extent of her broader emotional range.

As one of the most distinctive vocalists in country music, Tucker tackles the ballad with her signature bluesy, rasp to stellar heartfelt results. Singing with such understood precision of loss and love, she is able to fully embody the tale because it’s evident she’s lived it herself.

- Soda Canter

Mark Chesnutt - Bubba Shot the Jukebox

Anyone wondering what hold Mark Chesnutt had on country music in the '90s needs only to be reminded that the neo-traditionalist from Beaumont, Texas, notched a whopping great 20 Top 10 hits on the Billboard Hot Country Songs chart between 1990 and 1999.

Although 'Bubba Shot the Jukebox' might not have been his biggest at the time, it's gone on to be the song most associated with him.

Taken from his 1992 album, Long Necks and Short Stories, the song tells the story of a quiet night down at a local bar when someone unthinkingly puts a sad song on the jukebox. Triggered by the song's melancholy sentiment, one of the locals–the titular "Bubba" –storms out of the bar to his car to get his shotgun and comes back to fill the jukebox with lead.

He is arrested for reckless discharge of a firearm, showing a clear disregard for people's safety and presumably for the sanctity of sad country songs. In his defence, Bubba claims, "I shot just where I was aiming" and denies the "reckless" nature of the charge.

- JO

Terri Clark - Better Things To Do

We implore you to name a better debut for a country artist than Terri Clark’s ’Better Things To Do’.

The rollicking opus, so full of fearless words and an unstoppable sound, marked the Canadian star’s introduction to the genre in 1995 and quickly secured her place among its many stars of the decade.

’Better Things To Do’, written by Clark, alongside songsmiths Tom Shapiro and Chris Waters, became a certified hit on the US country songs chart and across the airwaves of her native Canada, peaking at No. 3 in both countries.

The song would ultimately act as the springboard for Clark’s career, one that would see successes like ‘Girls Lie Too’ and her version of ‘Poor, Poor Pitiful Me’ follow.

- AP

John Anderson - Straight Tequila Night

After a dry spell on the charts, John Anderson re-established himself as one of the great country artists of the ‘80s and ‘90s with 1991’s ‘Straight Tequila Night’.

Featuring Anderson’s evocative vocal delivery–which feels strongly reminiscent of Keith Whitley here–this liquor-drenched anthem follows a bar-tender that attempts to advise a man against making advances on a heartbroken woman (“Don't ask her on a straight tequila night / She'll start thinkin' about him, then she's ready to fight”).

‘Straight Tequila Night’ hit the peak of Billboard’s Hot Country Songs ranking, marking Anderson’s first No. 1 single in almost a decade and his new partnership with producer James Stroud helping him to instigate a momentous comeback.

The song received a coveted ACM Awards nomination for Single Record of the Year, and its smooth, meandering ambience has ensured this remains a go-to country classic.

- MM

Neal McCoy - Wink

The second of two back-to-back No. 1 country singles for Neal McCoy in the mid-90s, 'Wink' followed 'No Doubt About It' to the top spot in 1994 and went on to pick up the BMI award for the most-performed country song of the year.

It's no wonder it was ubiquitous that year.

The happy clapping country anthem is guaranteed to put a smile on your face no matter what you're going through. With it's feel good message that there's no need to turn to drink and psychoanalysis to solve your anxieties when all it takes is a loving wink of approval from a loved one to turn your worries around.

Bubba wouldn't be shooting up the jukebox if someone had put 'Wink' on, that's for sure.

- JO

Toby Keith - How Do You Like Me Now?!

Toby Keith’s ‘How Do You Like Me Now?!’ Name a more iconic tune. We’ll wait.

The catchy rock-flecked epic was a triumph at the turn of the millennium and it’s still a hit today. However, the 1999 tune, penned by Keith with his frequent songwriting companion Chuck Cannon, wasn’t an immediate success. In fact, it took a while for the song to find a home.

According to a 2005 Billboard interview, Keith’s then-label Mercury Records Nashville rejected ‘How Do You Like Me Now?!’ and much of the album, forcing the artist to seek out a new home at the now-defunct DreamWorks Nashville.

The tune eventually breathed life and went on to infiltrate the airwaves where it soared to the top of the Hot Country Songs chart and became a crossover hit, reaching No. 31 on the Hot 100.

Today, the song is still loved far and wide, having seen a resurgence with the star’s passing in February 2024.

- AP

Brad Paisley - We Danced

As we all know, country music is all about storytelling, and oftentimes, it's the simplest stories that go on to stand the test of time, as is the case with Brad Paisley's 'We Danced.'

A bartender closing up for the night and an unsuspecting woman who forgot her purse. They start talking, hitting it off, and the bartender says he'll give the purse back after one little dance together.

They end up falling in love and living happily ever after (we suppose), but the real charm in 'We Danced' is its utterly simplicity. There's no rhyming schemes or mind blowing turns of phrase, it's merely Paisley doing what he does best with a story song, and you best believe it topped the Hot Country Songs charts.

- LF

Little Texas - God Blessed Texas

It’s not often that an unassuming country song by a fairly obscure country band becomes the unofficial theme song of an entire state… but perhaps we can make an exception for Little Texas’ ‘God Blessed Texas.’

Released in 1993 as the second single from their sophomore album, Big Time, ‘God Blessed Texas,’ in the same way as most of Cody Johnson’s repertoire, celebrates the pride of those hailing from the Lone Star State, explaining that Texas is so great that God surely must’ve spent a little extra time perfecting the U.S.’s 28th state when he was expertly crafting it.

What is indisputably the band’s biggest hit and signature song–being in regular rotation at Dallas Cowboys and Texas Rangers games–debuted at No. 75 on the Billboard Hot Country Songs chart and eventually peaking at No. 4, while also securing No. 55 on the Hot 100.

- LF

Brooks & Dunn - Boot Scootin' Boogie

Though 'Boot Scootin’ Boogie' was written by Ronnie Dunn, it received the western swing treatment of West Virginia band Asleep at the Wheel with a stiff-collared, strait-laced rendition in 1990 before finding its way back to its owner.

Asleep at the Wheel’s version elicited polite nods and even politer toe taps, but it wasn’t until the track was back in the hands of Dunn and his collaborator Kix Brooks that it set dance floors alight.

Becoming so popular that it even got its own official choreography, the song was from the duo’s 1991 album Brand New Man and set the stage for a line dancing revival in the USA, bolstered by the release of Billy Ray Cyrus’ 'Achy Breaky Heart' the following year.

Perhaps disproving the old adage that "third time’s a charm," Brooks & Dunn have re-recorded the song twice for their Reboot albums, once with Midland and once with Haelstrom, but it’s the original that reigns supreme. With its country rock production, strategically placed fiddle, characteristically Brooks & Dunn lyrics full of hard-working men, and Dunn’s enthusiastically gruff vocal, the track’s charm only continues to grow with time.

- Holly Smith

Shania Twain - That Don't Impress Me Much

On her third studio album, Come On Over, Shania Twain set out to push her country sound forward while sharing her perspectives on female empowerment.

The pop country smash, ‘That Don’t Impress Me Much,’ succeeded at both and was not just a resounding success in the United States, but eventually became her most successful single worldwide.

Co-written with her then husband and producer Mutt Lange, Twain allows her keen ear and ample sense of humor to take flight. Between name dropping the likes of Brad Pitt and donning a hooded leopard outfit for the video, Twain was a savant at not just releasing music but creating a cultural phenomenon.

Now that does impress me much.

- SC

Wynonna - No One Else On Earth

“No one else on Earth could ever hurt me / Break my heart the way you do / No one else on Earth was ever worth it / No one could love me like / No one could love me like you…”

‘No One Else On Earth’ would mark a shift in the trajectory of Wynonna Judd’s career. The solo debut, which was released shortly after the dissolution of The Judds’ decade-long run together, would be a triumph for the artist, successfully carving out a lane in which Wynonna would shine solo.

The 1992 pop country hit, penned by written by Jill Colucci, Stewart Harris and Sam Lorber, topped the Hot Country Songs chart, found a home in Adult Contemporary and entered the pop charts, coming in at No. 83 on the Billboard Hot 100.

Today, ‘No One Else On Earth’ remains one of Wynonna’s biggest successes and Wynonna continues to shine.

- AP

Chely Wright - Single White Female

Chely Wright’s breakout single, ‘Single White Female’, blossomed into a smash hit towards the tail-end of the decade, with the energising, infectious chart-topper putting an end to Lonestar’s record-breaking run at No.1 on the US Hot Country Songs chart.

It’s a bright, playful and unashamedly country hit, which features harmonies from fellow female country powerhouse Trisha Yearwood throughout.

Compared to Wright’s slow-burning 1997 hit, ‘Shut Up and Drive’, ‘Single White Female’ feels looser and more light-hearted, with Wright's sleek, honeyed vocals gliding across the uptempo, guitar-driven instrumental.

Today, in light of Wright’s more intimate, soul-baring and Americana-leaning material of the 2010s, the commercial country of ‘Single White Female’ is a testament to her versatility.

- MM

Clay Walker - If I Could Make a Living

If you're looking for ways to avoid the sophomore slump, then bringing in Alan Jackson, Keith Stegall and Roger Murrah is a certified way to go about it.

Taken from Clay Walker's second studio album in 1994, the title track had all the hallmarks of an AJ '90s country classic, and it was no surprise when it replaced Jackson's 'Livin' on Love' in the top spot.

It's long been argued that the ideal pop song should clock in between two and a half and three minutes, and if that's the case, then that explains why, at two minutes and 14 seconds long, 'If I Could Make a Living' is one of the most perfect country-pop songs of all time

The song was also one of a number of country hits in the '80s and '90s about being unfulfilled and unhappy at work – along with songs such as Keith Whitley's 'Quittin' Time' – that reflected a wider shift in society away from traditional blue collar industries and towards the service industries.

- JO

Pam Tillis - Maybe It Was Memphis

“Maybe it was Memphis / Maybe it was southern summer nights / Maybe it was you, maybe it was me / But it sure felt right…”

‘Maybe It Was Memphis’ was a smash success when Pam Tillis released the thundering country rock ballad as the fourth single of her 1991 album, Put Yourself In My Place.

The Michael Anderson-penned tune not only landed her in the Hot Country Top 10, but it also earned her a nod for Song of the Year at the CMAs, as well as her first Grammy nomination for Best Female Country Vocal Performance.

Today, ‘Maybe It Was Memphis’ still stands out among Tillis’ hit-riddled catalogue as the tune that stole our hearts and steals our voices every time we try to hit those notes.

- AP

Kid Rock - Cowboy

“I want to be a cowboy, baby.”

Dubbed one of the “ten worst songs about cowboys” by the Houston Press, yet one of the artist’s best songs, this Kid Rock offering falls into his signature mix of hip-hop, southern rock and heavy metal, and has often been cited as the first “country rap” song, spawning viable paths for the likes of Jelly Roll, Colt Ford, Cowboy Troy and so many more since its release in 1999.

With a cocktail of Jew's harp, blues harmonica and a rocking guitar lick, coupled with his idea of moving to California to become a pimp and start an escort service atop the Four Seasons Hotel, ‘Cowboy’ isn’t exactly one of those songs that divulge a lot of profound meaning, but it’s damn fun to listen to and was a staple of the 1990s for obvious reasons.

Kid Rock called the song a cross between Run DMC and Lynyrd Skynyrd, and that’s pretty on the nose if you ask us.

- LF

Sammy Kershaw - She Don't Know She's Beautiful

With its winks of beachy electric guitar, subtle fiddle and sweet sentiment of admiration for Sammy Kershaw’s illustrious partner, 'She Don’t Know She’s Beautiful' wasn’t exactly foreshadowing of the extra-curricular career he would go on to have.

Having variously run as a candidate for lieutenant governor of Louisiana, been an advocate for the protection of Louisiana coastline and even taken a remodeling job at Walmart, the 1993 hit remains the assuredly more relaxed jewel in his country music crown.

Written by Paul Harrison and Bob McDill, the latter of whom was responsible for hits like 'Louisiana Saturday Night,' One Direction may have a lot to thank them for, given the almost identical message expressed in their debut track 'You Don’t Know You’re Beautiful.'

Yet, despite the mutual affections they hold their partner in, it’s Kershaw’s hit that continue to find spins on country dance floors, bringing it in at No. 31 on our list.

- HS

Shenandoah - Two Dozen Roses

Written by songwriting legends Mac McAnally and Robert Byrne, ‘Two Dozen Roses’ would become Shenandoah’s third No. 1 hit on the Billboard charts, alongside previous hits ‘The Church on Cumberland Road’ and ‘Sunday in the South.’

Apart from seamless harmonies from Shenandoah, it’s truly Rick Hall and Robert Byrne’s vintage inspired production that allows the pleadings of the narrator to resonate.

When Marty Raybon tenderly sings, “If I really could’ve hung the moon / Would it change your mind?” it’s impossible not to feel the lonely cold winds on the doorstep while his lover listens behind her locked door.

- SC

Tracy Lawrence - Paint Me a Birmingham

Few songs hurt as good as Tracy Lawrence's 'Paint Me A Birmingham.'

Written by Buck Moore and Gary Duffy, Lawrence wasn't the only one who knew the tune would be a hit, as country artist Ken Mellons also cut the song and charted it within one week of the version that's gone on to stand the test of time.

Only rising to No. 4 on the Hot Country Charts–but impressively peaking at No. 42 on the Hot 100–'Paint Me A Birmingham' finds a heartbroken man stumble upon a street artist, asking him to paint a canvas of the life he could've had if he wouldn't have lost the girl of his dreams, referencing a Birmingham-style house, as opposed to the Alabama city (though you could've fooled us).

If you only get one thing out of this list, understand that no one can do heartbreak quite like country music.

- LF

Dwight Yoakam - Fast As You

Despite remaining a keystone of Dwight Yoakam’s expansive discography, ‘Fast as You’ never quite made it to No. 1.

Nonetheless, it’s a rip-roaring demonstration as to why Yoakam has retained his status as one of country music’s trailblazers, with the rock-tinged sonics of the song setting the Kentucky crooner apart from the polished production and pop-leaning aesthetic opted for by many of his contemporaries.

‘Fast as You’ finds Yoakam lamenting the speed at which his old flame has gotten over him (“Maybe someday I'll be strong / Maybe it won't be long / I'll be the one who's tough, yeah / You'll be the one who's got it rough”), with his charismatic croon combining with the raucous, rockabilly-inspired instrumental.

- MM

Diamond Rio - Meet In the Middle

The debut single from Diamond Rio, released in February 1991, 'Meet in the Middle' took them all the way to the top spot on the Billboard Hot Country Singles chart and became the first of 16 Top 10 hits for the band in the '90s, setting them up to dominate the CMA and ACM Awards in the vocal group categories over the next five years.

The song itself is a simple enough tale of two young lovers living "seven hundred fenceposts" apart whose romance relies on them meeting each other halfway at a pine tree equidistant between their two houses.

The song remains as popular today as it did when it was released, with its high gloss country production and message of benevolence and acceptance of other people's differences in order to get along.

- JO

John Michael Montgomery - Sold (The Grundy County Auctioneer)

You can’t talk about country vocalist John Michael Montgomery without the mention of ‘Sold (The Grundy Country Auction Incident)’, and that’s because you can’t have one without the other.

Sure, Montgomery has had a laundry list of hits – 'I Swear,' 'Be My Baby Tonight,' 'I Can Love You Like That' and so on – over the course of his career, but the artist and ‘Sold’ will be forever inseparable. Plus, there’s no one else who can fire off the tongue-twister tune quite like the man himself.

When it was released in the early summer of 1995, the auction-esque bop went No. 1 just weeks later, topping the country charts in the U.S. and Canada and ear-worming its way into the annals of country classics.

- AP

Rhett Atkins - That Ain't My Truck

For those uninitiated, Rhett Atkins is the revered singer-songwriter father of modern hitmaker Thomas Rhett, and before TR was out and about making the girls swoon with his country-pop standards, his dad tried his hand at the artist thing first.

Without a question the biggest hit from his rather short-lived singing career is none other than ‘That Ain’t My Truck,’ a little ditty released in 1995 from his debut album, A Thousand Memories. While the rest of the record is largely forgettable, ‘That Ain’t My Truck’ spent a whopping 21 weeks on the Billboard Hot Country Songs chart, eventually peaking at No. 3.

An up-tempo weeper, Atkins finds himself on the losing end of a relationship as his beloved finds another guy with a truck to park in her driveway in the same place that Atkins used to.

It’s a classic country trope that should’ve just been another rinse and repeat, but there’s something about the way that Atkins bottled it up and distilled it that still hits folks right in the feels even 30 years later.

- LF

The Mavericks - Dance the Night Away

True to its own roots as a certified feel-good party song that masterfully blends latin, pop and country influences, The Maverick’s 1998 floor-filler was born out of chance in proof of the good fortune that can come your way when you just let loose and kick back.

Lead singer Raul Malo was strumming away one afternoon when he realised that his absent-minded noodling sounded like a song. “It just kind of wrote itself as I messed with it,” he said.

The real stroke of genius comes in the song’s iconic horn section, ceremoniously heralding the narrator’s freedom as he turns back to happiness after a relationship ends, and enjoys the universal pleasures of senoritas and a bright tomorrow.

Simple, relatable, toe-tapping – it’s proof that brilliance needn’t be complicated.

- HS

Lonestar - Amazed

From their third studio album, 1999’s Lonely Grill, ‘Amazed’ became Lonestar’s longest running No. 1 hit on the Billboard charts that had both an original country version and a pop remix.

The power ballad resonated with listeners around the world as it encapsulated the sheer wonder of being in a loving relationship as told through the resonant vocals of Richie McDonald.

The pop remix would become the first power ballad to reach the height of the Hot 100 chart since Aerosmith’s ‘I Don’t Want to Miss a Thing’ and the first new country song since Kenny Rogers and Dolly Parton’s beloved duet ‘Islands in the Stream.’

- SC

Kenny Chesney - She Thinks My Tractor's Sexy

Candidly one of the more ridiculous entries on this list, simply by way of lyrical content, you'd be hard pressed to say that this isn't one of both Kenny Chesney's and the '90s most iconic songs.

Just your average song about a tractor-driving farmer and his fling with the girl next door, 'She Thinks My Tractor's Sexy' was written by Jim Collins and Paul Overstreet and included on Chesney's 1999 record, Everywhere We Go.

Now a 2x Platinum signature song in Chesney's catalogue, the tune didn't really connect at radio during its heyday, only peaking at No. 11 on the Hot Country Songs chart and spending 21 total weeks among the ranks.

It's obvious that chart placement isn't everything, though, seeing as the Knoxville native has rarely ever left the song out of his setlists over the last 25 years.

- LF

Brooks & Dunn - Neon Moon

When you think of the essence of ‘90s country, it’s hard not to picture Brooks & Dunn’s outrageous–and often flame-adorned–costumes and their penchant for quirky, tongue-in-cheek and self-effacing narratives.

The duo have produced a host of the genre’s defining hits, and what makes this particularly impressive is the fact that three of their most influential chart-toppers–‘Neon Moon’, ‘Boot Scootin’ Boogie’ and ‘Brand New Man’–all appeared on their debut album.

‘Neon Moon’ has been covered by just about every big-name contemporary country artist, and was revamped with Kacey Musgraves and Morgan Wallen as part of Brooks & Dunn’s Reboot and Reboot II projects, respectively. Penned by Ronnie Dunn before Brooks & Dunn had even met, ‘Neon Moon’ snakes along a hazy, undulating guitar riff, with Dunn’s ear for a killer melody radiating throughout both the verses and addictive hook.

A karaoke staple, the song remains one of the most recognisable country songs of the past fifty years, with Brooks & Dunn stripping back the swagger and strut of ‘Brand New Man’ and ‘Boot Scootin’ Boogie’ for this beautifully pared-down and intricate gem.

- MM

Vince Gill - Go Rest High on That Mountain

Anyone that has ever watched Vince Gill and Patty Loveless blub their way through 'Go Rest High On That Mountain' at George Jones' funeral will know the enduring power of this timeless country gospel song from Gill's 1995 album, When Love Finds You.

Gill originally began writing the song following the death of country music singer Keith Whitley in 1989 but wouldn't finish the song until a few years later following the death of his older brother Bob of a heart attack in 1993. With its message of finding peace in death after a difficult life, the song felt particularly poignant being sung at Jones' funeral, held at the Grand Ole Opry on May 2, 2013.

"I know your life on earth was troubled and only you could know the pain / You weren't afraid to face the devil / You were no stranger to the rain."

It takes an almost Squid Game level of endurance to get through the performance without breaking down into sobs. The less emotionally available of you might be able to make it through the opening verses, but when Garth and Trisha stand up in the front row and Nancy Jones is visibly crying in shot, we defy any of you to keep it together. If you're not crying when Patty leaves her microphone to cross the stage and console an openly weeping Vince Gill, then you should go and see a doctor because you have no heart at all.

- JO

Jo Dee Messina - Heads Carolina, Tails California

Jo Dee Messina’s ‘Heads Carolina, Tails California’ was thrust back into country consciousness in 2022 when Cole Swindell released ‘She Had Me at Heads Carolina’, a cheeky spin on the classic track. However, the knock-off song paled in comparison to Messina’s hit debut single from 1996.

That’s right, the country pop opus, written by Tim Nichols and Mark D. Sanders, was the singer’s introduction to country music, and what an intro it was.

While ‘Heads Carolina, Tails California’ soared up the Hot Country Songs chart upon its release, it surprisingly never reached No. 1, stalling at No. 2 just behind Brooks & Dunn’s ‘My Maria.’ The tune, however, would open the door for so many more hits, like the star’s ‘Bye Bye’ and ‘I’m Alright’, to flood in.

Still, it’s that debut song that has endured throughout Messina’s career.

- AP

Tracy Byrd - Watermelon Crawl

Now, listen here. If you want to know one of the best line dance songs in country music history, look no further than Tracy Byrd’s ‘Watermelon Crawl.’

Before there was Dasha’s viral ‘Austin’ dance and all these other TikTok songs popping off left, right and center, the ‘Watermelon Crawl’ was and still is a staple at honkytonks, dive bars and line dances all across the country, and we frankly can’t see that changing anytime soon.

Written by Buddy Brock and Zack Turner, it was released in 1994 as the second single from Byrd's No Ordinary Man record. Peaking at No. 4 on the country charts and No. 81 on the Billboard Hot 100, the tune centers around (what else?) a watermelon festival in the fictional Rind County, Georgia.

Sipping on red wine made from the prized watermelons, the township decides that instead of drinking and driving, they’d think up a snazzy dance that we now know as the ‘Watermelon Crawl.’

And thus, the iconic dance was born.

- LF

David Lee Murphy - Dust on the Bottle

'Dust on the Bottle' may have hit the airwaves in 1994, but as a hangover from the '80s with its heartland rock, road trip vibes and laid back self-confidence, it’s as solid as the proof of the liquor filling its titular vestibule.

“There might be a little dust on the bottle but don’t let it fool ya about what’s inside / there might be a little dust on the bottle but it’s one of those things, it gets sweeter with time,” Murphy croons smoothly, honouring one of country music’s thematic fail-safes in its celebration of love and objects that stand the test of time, no matter how weathered they may be.

Murphy’s biggest hit, which he claimed to have written in 15 minutes, it hailed from his 1994 debut album, Out With A Bang, to give him a No. 1.

His songwriting chops have continued to prove valuable ever since, as he’s built an extensive career writing hits for the likes of Jake Owen, Kenny Chesney and Jason Aldean. When Post Malone invited Murphy to join him on stage for a rendition of the song in August of 2024, it remained as playful and joyous as ever, bringing it in at 17 on our list.

- HS

Travis Tritt - Here's A Quarter (Call Someone Who Cares)

‘Here’s a Quarter (Call Someone Who Cares)’ was written solely by Tritt for his 1991 bestselling, triple Platinum album, It’s All About to Change.

The song would become an eventual hit, rising to the No. 1 spot on the Hot Country Song charts. Tritt rarely receives the due accolades for his songwriting, especially his tongue-in-cheek sense of humor, but the inventive structure of ‘Here’s a Quarter’ is a testament to his superb talent.

More than a beer-to-the-sky singalong worthy single, Tritt would inspire legions of those that have been done wrong with a catch phrase tell-off that would retain its bite long after payphones met their demise.

- SC

Reba McEntire - Fancy

‘Fancy’ was a hit when sultry country vocalist Bobbie Gentry released it in 1970, but it would be Reba McEntire who would make the hardscrabble story song a standard.

Her version of the Gentry-penned tune was released in 1991 as the third single of her album, Rumor Has It. The song would be met with great acclaim from fans and critics alike, climbing to No. 8 on the Hot Country Songs chart, a giant leap from Gentry’s peak position at No. 26 on the same ranking.

The two versions of the tune are, of course, classics, but McEntire’s rendition, with its fired up arrangement and attitude-flecked delivery, is still considered among the greatest works of country today.

- AP

Joe Diffie - Pickup Man

Joe Diffie’s ‘Pick-Up Man’ stands as a welcome reminder that some of the best country songs are the ones that don’t take themselves too seriously, with Diffie’s hilarious, punchline-packed anthem combining stellar wit with irresistible musicality.

The single spent four weeks at No. 1 on Billboard’s Hot Country Songs chart from 1994 to 1995, with the braggadocio-infused hit enjoying a resurgence in popularity when it was reimagined into a posthumous duet with Post Malone in 2023 as part of HARDY’s HIXTAPE: Vol. 3: DIFFTAPE.

With lyrical highlights including “You can set my truck on fire and roll it down a hill / And I still wouldn't trade it for a Coupe DeVille,” and the riotous “I met all my wives in traffic jams,” ‘Pick-Up Man’ cemented Diffie’s status as a ‘90s country legend.

- MM

Billy Ray Cyrus - Achy Breaky Heart

Although its often on lists of the worst songs of the '90s–an opinion not helped by Billy Ray Cyrus' disastrous performance of the song at Donald Trump's Liberty Ball following the presidential inauguration in 2025–there's no denying how much 'Achy Breaky Heart' defined '90s country for a lot of people when it was lifted from his debut album, Some Gave All, in 1992.

A worldwide crossover hit, the song reached No. 4 on the Billboard Hot 100 and No. 3 on the UK Singles Chart, as well as topped the Hot Country Singles chart and went on to become the first country single to be certified Platinum since Dolly and Kenny's 'Islands in the Stream' in 1983.

With its blend of '90s pop country gloss and boogie woogie backbeat, 'Achy Breaky Heart' had us all unexpectedly grapevining and quarter turning as it became one of the songs responsible for kick starting the global line dance phenomenon in the '90s.

- JO

Deana Carter - Strawberry Wine

“Like strawberry wine and seventeen / The hot July moon saw everything / My first taste of love, oh bittersweet / Green on the vine / Like strawberry wine…”

Love it or hate it, you’ll likely always sing along to ‘Strawberry Wine.’ It’s as natural as the changing of the seasons, as inevitable as the Earth’s orbit.

Just as it still does today, the Deana Carter classic had a chokehold on country music when it was released in the summer of 1996. The debut single of her debut album, Did I Shave My Legs for This?, ’Strawberry Wine’ reached No. 1 on the Hot Country Songs chart and crossed over into the mainstream, peaking at No. 65 on the Hot 100.

’Strawberry Wine’ is still Carter’s biggest hit and we’ll keep singing the coming-of-age tune as long as there are hot July moons to enjoy and first loves to experience.

- AP

Tim McGraw - I Like It, I Love It

You know it, you love it and you probably want some more of it, too.

Tim McGraw’s third No. 1 single (out of an impressive 30 across his career), this 1995 hit has endured well beyond its expiration date at country radio, though it fared pretty well there, too, in its heyday.

Released as the first single from his All I Want record and recorded at the famed FAME Studios in Muscle Shoals, Alabama, ‘I Like It, I Love It’ debuted at No. 50 on the Hot Country charts before eventually ascending to the top spot. The song ended 1995 as the No. 3 country song on Billboard’s year-end chart and has since been certified 2x Platinum by the RIAA, just in case you needed more proof of its staying power.

While truly nothing special lyrically, it’s become one of McGraw’s standard hits, even going so far as to be used as the official song of the Nashville Predators when the NHL team scores a goal, replacing the line "don't know what it is about that little girl's lovin'" with "don't know what it is about the Predators scorin'."

Shakespeare would be proud.

- LF

Martina McBride - Independence Day

You can’t rush perfection and Gretchen Peters would know. She spent 18 months writing 'Independence Day', the intriguingly upbeat song about escaping domestic abuse that found success when recorded by country star Martina McBride for her 1993 album, The Way That I Am.

With a powerful vocal that looks straight down the barrel of an '80s power ballad, McBride’s version of the track is the fiery and defiant story of a woman who breaks away from a violent relationship, told from her daughter’s perspective.

In the long tradition of country murder ballads, the song ends dramatically as the narrator’s mother "lit up the sky like the fourth of July," burning down her house and taking her husband with it. While lyrics like "talk about your revolution / It’s Independence Day / Let freedom ring / Let the white dove sing" have inevitably led the song to be repurposed as an anthemic song in celebration of the USA, Peters has rejected any political narrative attached to it.

Whichever way you look at it, the track’s ability to galvanise its listener in air punching triumph has made it a mainstay on country playlists for the past 30 years.

- HS

LeAnn Rimes - How Do I Live

The songwriting machine often produces hits so obvious that multiple artists clamour over them, but it’s a rare instance when two major artists end up recording the same track and then releasing it on the same day.

Written by Diane Warren, of ‘I Don’t Wanna Miss a Thing’ and ‘If I Could Turn Back Time’ songwriting fame, ‘How Do I Live Without You’ was first recorded by 14-year-old LeAnn Rimes for the film Con Air. The filmmakers, having decided that Rimes’ version was not mature enough, enlisted established country star Trisha Yearwood to record her own version.

Whilst Yearwood’s rendition was used in the film, both versions of the song were released to radio on May 23, 1997. Yearwood’s version won a Grammy and afforded Warren one of her 16 Oscar nominations for Best Original Song, but Rimes’ version achieved a level of crossover success that has seen her occupy an unmoving place in millennial hearts ever since.

With its soulful, acrobatic vocal and sweet pop production, karaoke machines have not been safe since.

- HS

Trisha Yearwood - She's In Love With the Boy

Released in the spring of 1991, ‘She’s in Love With the Boy’ would serve as the first single off the self-titled debut album of a little known Nashville demo singer named Trisha Yearwood.

Written by Jon Ims, the song detailed the imperfect love story of Katie and Tommy and was rewritten nearly 32 times before Ims believed he had structurally done the story justice.

Yearwood’s timeless vocal performance would not just immediately capture the hearts of listeners, but would push ‘She’s in Love With the Boy’ to become her first of five No. 1 singles on the Billboard charts.

- SC

Garth Brooks - Friends in Low Places

"Blame it all on my roots, I showed up in boots / And ruined your black tie affair."

Honest to God, name a more iconic pair of opening lines to any song ever.

A song synonymous with Garth Brooks, and now the name of the country legend's bar on Nashville's Broadway, 'Friends In Low Places' was a smash success from the word go.

The lead single to his lauded No Fences album and written by Earl Bud Lee and Dewayne Blackwell, 'Friends In Low Places' only took eight weeks to ascend to the top of the Hot Country Songs chart, remaining there for four weeks. The following year, it also managed to sweep the Single of the Year category at both the CMA and ACM Awards ceremonies, beating out the likes of Alan Jackson's 'Don't Rock The Jukebox,' Travis Tritt's 'Here's A Quarter,' Vince Gill's 'When I Call Your Name' and others.

With all of that being said, only the real fans know the secret third verse... let the Google searches commence.

- LF

George Strait - Check Yes or No

Throughout his career, George Strait has often infused an endearing sense of innocence into his music, epitomised on his 1995 No. 1, ‘Check Yes Or No’.

n the hands of anyone other than King George, ‘Check Yes Or No’ would easily descend into overly twee or saccharine territory, but somehow, Strait manages to lace his trademark sincerity and gravitas into his delivery, elevating this into a feel-good earworm.

Revolving around a childhood romance, the sweet, mild-mannered protagonist courteously hands a girl a note in class, reading, “Do you love me? Do you wanna be my friend? / And if you do / Well then don't be afraid to take me by the hand / If you want to / I think this is how love goes / Check yes or no”.

Fast-forward a few decades, the couple in question are now man and wife, with Strait regaling listeners with this heartwarming narrative across the ubiquitous cry of a yearning steel-guitar.

- MM

Faith Hill - This Kiss

For some of us, 'This Kiss' will be forever associated with the 1998 movie Practical Magic starring Sandra Bullock and Nicole Kidman as witchy sisters Sally and Gillian Owens who must use their magic to destroy the evil spirit of Gillian's abusive boyfriend before it kills them... but the song has bewitched country audiences ever since its release.

As well as perfectly capturing that feeling when love feels powerful enough to overcome any obstacle that stands in its way, Byron Gallimore's production on 'This Kiss' sounds as fresh today as it did nearly 30 years ago, and it's for these reasons that the song claims its place in the Top 5 of our Best '90s Country Songs.

Taken from Hill's third studio album, Faith, the song became a huge crossover hit reaching the Top 10 on the Hot 100 and No. 13 in the UK. It was nominated for Best Female Country Vocal Performance and Best Song at the Grammy Awards in 1999, but lost out to Shania Twain's 'You're Still the One' both times.

- JO

Toby Keith - Should've Been a Cowboy

Few songs from the decade hold a candle to Toby Keith’s ‘Should've Been A Cowboy’.

Released in 1993 as the debut single of his debut album, the tune was Keith’s first official hit and would mark the beginning of what would be untouchable success.

The catchy country epic about “the good old days” of roping, riding and cow-poking around the American West, ‘Should've Been A Cowboy’ would earn Keith his first No. 1 on the Hot Country Songs chart and become a crossover hit, peaking at No. 93 on the Hot 100.

With his passing in February 2024, the song would see a resurgence, re-entering the Hot Country charts alongside several of his greatest hits. Even today, ‘Should've Been A Cowboy’ bests many of the tunes in his hit-ridden repertoire, currently boasting hundreds of millions of steams across platforms.

- AP

The Chicks - Goodbye Earl

Throughout country music’s history, there have been a long string of murder ballads.

Miranda Lambert's 'Gun Powder & Lead,' Taylor Swift's 'no body, no crime,' Carrie Underwood's 'Two Black Cadillacs,' Kelsea Ballerini's 'IF YOU GO DOWN (I'M GOING DOWN TOO)'... that's a lot of women singing about killing some lying, cheating, no good men in their lives, and arguably, none of them would be such hits were it not for The Chicks' 'Goodbye Earl.'

Released in 1999 on their fifth record, Fly, it’s a perfect marriage of Fried Green Tomatoes and Thelma & Louise as two best friends plot the murder of one of their abusive husbands, Earl.

"It didn't take 'em long to decide / That Earl had to die / Good bye, Earl / Those black-eyed peas / They tasted alright to me, Earl / You feelin' weak? / Why don't you lay down and sleep, Earl / Ain't it dark wrapped up in that tarp, Earl."

Originally sparking controversy due to its violent themes and mentions of domestic violence, the song ended up bringing much needed awareness to the issue as radio stations provided phone numbers to hotlines before playing the song on their airwaves. 'Goodbye Earl' peaked at No. 13 on the Billboard Hot Country Songs chart while also squeaking its way into the Top 20 of the Hot 100, cementing itself as one of The Chicks' most well-known and well-loved songs.

Beyond all that, if you haven’t seen the music video for ‘Goodbye Earl,’ do yourself a favor and get the popcorn ready.

- LF

Shania Twain - Man! I Feel Like a Woman!

Iconic might be an overused word, but there are some musical moments that truly fit the definition.

The seven opening notes of Shania Twain’s 1999 pop-country juggernaut are enough to send entire dance floors into frenzies, activating a reflex so deep that even the coolest and most cynical are compelled to respond in unison, "Let’s go girls."

Written by Twain and her then-husband Robert Lange, 'Man! I Feel Like A Woman', appeared on Twain’s 1997 album, Come On Over, winning a Grammy for Best Country Vocal Female Performance. Inspired in part by Twain’s time spent in Toronto’s gay bars and seeing drag performers as a young adult, the song is pure hedonism above all else, inviting the listener into a world of female empowerment where the expectations of being a "lady" are well and truly forgotten.

As with many of Twain’s party hits, it’s her unabashedly charming vocal, infinitely quotable lyrics and an unforgettable guitar riff that make it one of the most enduring pop country hits of the '90s.

- HS

Alan Jackson - Chattahochee

Co-written with Jim McBride, the third single taken from Alan Jackson’s album, A Lot About Livin’ (And a Little ‘Bout Love), would become one of his most celebrated songs, receiving the ACM and CMA’s Single of the Year trophies in 1993.

Alongside becoming a No. 1 single on the Hot Country Songs chart, it would also be his first entry into the Hot 100 territory.

Though, it’s easy to understand why it connected then and still engages today, with the foot tapping drum beats and guitar riffs of the opening. Jackson’s coming of age tale, no matter where one resides, charmingly captures the innocence of youth and celebrates the magical connection of being home.

- SC