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The Best 90s Country Songs

By Holler

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Ah, the 90s! The decade that gave us Harry Potter, Beanie Babies and super-sized fries. Everyone was doing the Macarena, and a new thing called Google could tell you anything you wanted to know on a pastel coloured Macbook (if you could get your dial-up connection to work).

It was also a big-time for country music... and big hair... and big hair IN country music.

As they say, everything old is new again, and it seems we are in the middle of a 90s country revival. Makes sense really, things seem to come back around again every 30 years or so.

But here's the thing about 90s country: it still sounds amazing today - and even, dare I say, current.

Not all of it of course - some themes have certainly dated less favourably than others. Diversity was basically non-existent on the country charts too, a damning sign of the state of the industry; frustratingly an uphill battle still being faced today.

Thankfully, though, women were shining bright and consistently dominating the charts. A string of powerful, superstar women were taking control - they had something to say and by god they were going to say it, and you were going to dance or cry to it (or in some cases both), whether you wanted to or not.

Sadly, in the following decades, the industry seemed to backslide. Women are yet again fighting for their rightful place on the radio and charts, walking the road paved by those before them, stomping out the weeds that have grown in the cracks since.

The more things change, the more they stay the same.

So, make sure your Tamagotchi has been fed, pause that rerun of Friends, and let’s run down the 50 top tunes of the 90s, as selected by our crack team of contributors, staff, and friends. Some who were actually alive in the ’90s and some who weren’t - but obviously wish they were. Let’s go girls!

- Baylen Leonard

Holler - The Best 90s Country Songs List

Holler - The Best 90s Country Songs

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50
Shania Twain - Come On Over - Album Cover

UMG Recordings | 1997

Shania Twain - That Don't Impress Me Much

This global smash hit broke into the top 10 in 16 different countries. A country pop banger, ‘That Don’t Impress Me Much’ is one of the catchiest in Twain’s repertoire; the lyrics oozing her characteristic playfulness and humour.

Surprisingly, given the songs longevity and global notoriety, it never actually topped the charts in the US. - Zoe Hodges

Thumbnail - That Don't Impress Me Much

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49
George Strait - Chill Of An Early Fall - Album Cover

MCA Records | 1991

George Strait - If I Know Me

It’s one thing to know your better half really, really well. But this quiet piano ballad turns that mirror around so that George Strait gets to know himself well enough to know exactly how things are going to turn out.

He’s going to turn the car around, say he’s sorry and go running back to her. It’s a quintessential '90s song that uses a play on words to reel you in. - Alison Bonaguro

Thumbnail - George Strait - If I Know Me

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48
Lorrie Morgan - Something In Red - Album Cover

RCA Records | 1991

Lorrie Morgan - Except For Monday

Lorrie Morgan pretends she is absolutely FINE!! in this toe-tapping tribute to messy breakups.

She bumps into her ex when she’s out clubbing on a Sunday night and lets him know just how okay she is with everything. Which it turns out she isn’t really. Well, not for most of the week anyway. - Jof Owen

Thumbnail - Lorrie Morgan - Something in Red

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47
Steve Earle - El Corazón

Warner Records | 1997

Steve Earle - Telephone Road (With The Fairfield Four)

Steve Earle’s tribute to a 10-mile long stretch of road in Houston captures him at the height of his powers in the late-90s.

He brings in American gospel legends The Fairfield Four for this joyously upbeat paean to the restlessness and desperation of small-town America. - JO

Thumbnail - Steve Earle - Telephone Road

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46
Clay Walker - If I Could Make A Living - Album Cover

BMG Entertainment | 1994

Clay Walker - If I Could Make A Living

Wouldn’t this be a nice gig? To just love someone for a living?

Clay Walker painted a vivid picture – with ample splashes of fiddle - of what that career goal would look like: becoming a millionaire in a week or two, loving that 8 to 5, never leaving her alone when he’s working overtime, doing what he loves and loving what he does. - AB

Thumbnail - Clay Walker - If I Could Make a Living

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45
Pam Tillis - Put Yourself In My Place - Album Cover

Arista Records | 1990, 1991

Pam Tillis - Maybe It Was Memphis

One of the hallmarks of the country genre is the story song, and Pam Tillis masters the art form on ‘Maybe It Was Memphis’.

A nostalgic love story set against a hot summer night in the south, Tillis’ epic vocal line cements the song’s place as one of the classics of the decade. - Carena Liptak

Thumbnail - Pam Tillis - Maybe it was Memphis

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44
Clint Black - One Emotion - Album Cover

BMG Entertainment | 1994

Clint Black - Summer's Comin'

Turn on CMT on any given summers day in the mid-90s and it wouldn’t be long before you were watching the video for this heels up honky-tonker.

Clint Black takes the day off work to hit the beach in a muscle vest and cycling shorts. Somehow still managing to style it out with a cowboy hat. - JO

Thumbnail - Clint Black - Summers Comin'

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43
Wynonna - Revelations - Album Cover

Curb Records | 1996

Wynonna - Change The World

Perhaps now better known for Eric Clapton’s version, ‘Change the world’ was first recorded by Wynonna Judd for her third album, Revelations.

Watching Wynonna sing it live was to witness true vocal prowess and control, as she moved away from the partnership with her mom Naomi into prized crossover territory. - Helen Jerome

Thumbnail - Wynonna Judd - Change the World

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42
Tracy Lawrence - I See It Now - Album Cover

Atlantic Records | 1994

Tracy Lawrence - If The World Had A Front Porch

“If the world had a front porch like we did back then / we'd still have our problems but we'd all be friends”, Tracy Lawrence sings in this wide-eyed celebration of traditional family values and simpler times.

In the music video, Lawrence gets zapped into a vortex and trapped in a quantum realm, singing the song on a CGI porch as it flies around the world. The 90s were really weird sometimes. - JO

Thumbnail - Tracy Lawrence - If The World Had A Front Porch

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41
Jo Dee Messina - I'm Alright - Album Cover

Curb Records | 1998

Jo Dee Messina - I'm Alright

This is a singalong that everyone loved in 1998. Jo Dee Messina added her sassiness to the story about a singer that’s down on her luck, but still happy.

"I've been singing for my rent and singing for my supper / I’m above the below and below the upper”.

I guess she was doin’ alright. - Kelly Sutton

Thumbnail - Jo Dee Messina - I'm Alright

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40
Son Volt - Straightaways - Album Cover

Warner Records | 1997

Son Volt - Back Into Your World

Three years after the breakup of alt-country’s most important band, Jay Farrar made the underrated masterpiece Straightaways.

A follow up to the equally magnificent Trace, it included this poetic Byrdsian jangle-pop classic and proved that Farrar was more than capable of doing anything his ex-Uncle Tupelo bandmate Jeff Tweedy could do; sometimes doing it even better too. - JO

Thumbnail - Son Volt - Back into Your World

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39
Patty Loveless - When Fallen Angels Fly - Album Cover

Sony BMG Music Entertainment | 1994

Patty Loveless - I Try To Think About Elvis

When you’re attempting to stop thinking about an ex, you’ll try just about anything. Patty Loveless gave us all a long list of about 23 alternatives to concentrate on instead: Elvis, Oprah, the cosmos, champagne, freight trains, Shakespeare and more.

But as the sassy singer admits, her mind wanders where it will, despite her attempts to get him out of her head. - AB

Thumbnail - Patty Loveless - I Try To Think About Elvis

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38
Dolly Parton - The Grass Is Blue - Album Cover

Sugar Hill Records | 1999

Dolly Parton - The Grass Is Blue

‘The Grass is Blue’, the title track off country music legend Dolly Parton’s 1999 album, intentionally gives a major clue to the fact that the record would embody a bluegrass sound.

Listening to the heartbreak single, you’d never expect that the writing process took place on Parton’s 30-minute lunch break. – Madeline OConnell

Thumbnail - Dolly Parton - Dolly Parton Norah Jones - The Grass Is Blue @ The CMAs

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37
Marty Stuart - Tempted - Album Cover

MCA Records | 1991

Marty Stuart - Tempted

This song might have only peaked at no.5 on the charts, but it’s a fave for us here at Holler!

Stuart is often known as a spokesman for the genre, encompassing all that country represents; honouring its roots whilst welcoming the future. From the lyrical content to the melodic hooks, with this hugely commercially successful song, he proves why. – ZH

Thumbanil - Marty Stuart - Tempted

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36
Dwight Yoakam - This Time - Album Cover

Reprise Records | 1993

Dwight Yoakam - Fast As You

More than most country songs of the 90s, ‘Fast as You’ proves that even hit singles of the genre can handle their fair share of rock ‘n’ roll inclinations.

‘Fast as You’ embarked on a new era of country music, one that combined the genre’s storytelling roots with a West Coast-inspired varnish of glitz and glamor. - CL

Thumbnail -Dwight Yoakam - Fast As You

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35
The Chicks - Fly - Album Cover

Colombia Records | 1999

The Chicks - Cowboy Take Me Away

The love story of Chicks member Emily Strayer and husband Charlie Robison inspired this 1999 hit. Co-writers Martie Maguire and Marcus Hummon imagined the couple riding off into the sunset together as young lovers.

The three-part harmony, released over 20 years ago on Fly, continues to grow in popularity with each generation. - MO

Thumbnail - The Chicks - Cowboy Take Me Away

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34
Randy Travis - High Lonesome - Album Cover

Warner Records | 1991

Randy Travis - Heart Of Hearts

‘Heart of Hearts’ is the third track off Randy Travis’ 1991 platinum high lonesome album.

The song is unapologetically honest with love the center of attention, the character portrayed in the lyrics grappling with the decision to refrain from cheating on his partner. - MO

Thumbnail - Randy Travis - Heart of Hearts

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33
Reba McEntire - Greatest Hits Volume 2 - Album Cover

MCA Records | 1993

Reba McEntire & Linda Davis - Does He Love You

One of those corny yet intense songs about a love triangle, this 1993 ballad found Reba recording with her backing singer, Linda Davis (mother of Lady A's Hillary Scott).

To show its timelessness, Reba has re-recorded the song in 2021 with Dolly Parton, their first-ever duet together. - HJ

Thumbnail - Reba McEntire - Does He Love You ft. Linda Davis

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32
Alison Krauss - Now That I've Found You (A Collection) - Album Cover

Rounder Records | 1995

Alison Krauss - Baby, Now That I've Found You

The breakthrough title track from her early retrospective collection, this heavenly cover unsurprisingly won a Grammy for Best Female Country Vocal in 1995.

Though she brings her own unique take to the song, Krauss' version is still highly reminiscent of the 1960s original by British soul group The Foundations. - HJ

Thumbnail - Alison Krauss and Union Station - Baby, now that I've found you

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31
Diamond Rio - Diamond Rio - Album Cover

Arista Records | 1991

Diamond Rio - Meet In The Middle

This was the world’s first taste of Diamond Rio, and what an introduction it was. This song is about literally and figuratively meeting in the middle of the 700 fenceposts between you and your love, first as teenagers then later as a married couple who don’t see eye to eye.

The story in this song hadn’t been told before, and it hasn’t been told as well in all the years since. - AB

Thumbnail - Diamond Rio - Meet In The Middle

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30
The Mavericks - Dance The Night Away - Single Cover

MCA Records | 1998

The Mavericks - Dance The Night Away

This horn-driven song blasted The Mavs into the UK Top 5 after they performed it on the British version of the Powerball show.

Songwriter Raul Malo has mixed emotions about what, in his eyes, is a nursery rhyme: “I feel like I have a million songs that are 10 times better”.

Even he can’t deny that it’s impossible to resist dancing to it once they strike up the horns. - HJ

29
Chely Wright - Single White Female - Album Cover

MCA Records | 1999

Chely Wright - Single White Female

Chely Wright’s first and only no.1 on the Hot Country Songs chart was this fun, upbeat, carefree love song.

The concept draws inspiration from a lonely hearts advert and features fellow country singer Trisha Yearwood on backing vocals. - ZH

28
Album - Lucinda Williams - Car Wheels On A Gravel Road

Mercury Records | 1998

Lucinda Williams - Can't Let Go

Of all the tracks on Lucinda Williams’ seminal 1998 album, Car Wheels on a Gravel Road, ‘Can’t Let Go’ is more than just a cornerstone of her discography.

It’s also the perfect microcosm of a particular moment in 90s alt-country history, one defined by the gritty freedom of the open road. - CL

27
John Prine - The Missing Year - Album Cover

Oh Boy Records | 1991

John Prine - All The Best

This 1991 song from The Missing Years album is a perfect summary of John Prine’s economic songwriting.

There’s a generosity of spirit as he tenderly says goodbye to a lover, but undercuts it by wishing that they “never fall in love with someone like you”. Masterly. - HJ

26
K.D. Lang - Ingenue - Album Cover

Sire Records, Warner Bros | 1992

k.d. lang - Constant Craving

Composed with her writing partner Ben Mink and released in 1992 – the “watershed” year lang came out as gay – the music came quickly on her Casio keyboard, but the lyrics were a struggle.

Crucially, this gem of desire and longing crossed over to win a Grammy for Best Female Pop Vocal. - HJ

25
Gretchen Peters - The Secret Of Life - Album Cover

Scarlet Letter Records | 1996

Gretchen Peters - On A Bus To St. Cloud

With a title grabbed from a random place name on a map, this song, originally a hit for Trisha Yearwood, established Peters in the UK.

Having sung the song from Nashville to London, she says she’ll keep performing it live as long as it continues to find new meaning over the years. - HJ

24
Garth Brooks - Garth Brooks - Album Cover

Capitol Records | 1989

Garth Brooks - The Dance

Taken from Brooks’ debut album, ‘The Dance’ topped the charts for three weeks, since becoming one of his signature songs.

The lyrics to this tragic track are flawless, capturing a double meaning both as a love song about the end of a relationship and a story of someone dying for something he believes in. - ZH

23
Shania Twain - The Woman In Me - Album Cover

Mercury Records | 1995

Shania Twain - Whose Bed Have Your Boots Been Under

Louise, Denise, Beverly, bloody Jill!! For goodness sake. Whose bed haven’t his boots been under more like?!

This perky give-a-shit done-me-wrong song was the first song that Shania wrote with her then-husband Mutt Lange and it became her first hit on country radio, peaking at number 11 in 1995. - JO

22
Kenny Chesney - I Will Stand - Album Cover

BMG Entertainment | 1997

Kenny Chesney - That's Why I'm Here

Like any solid country song in the 90s, this one told a compelling story about a guy trying to win his wife back by going to Alcoholics Anonymous meetings.

So in the beginning, after she’s kicked him to the curb, he shows up to tell her he’s sober. Because after a life of denial, he finally went to AA. By the end of the song, he’s invited her to join him at the next meeting. - AB

21
Brooks & Dunn - Brand New Man Album Cover

Arista | 1991

Brooks & Dunn - Neon Moon

Drowning your heartbreak under a tacky neon bar sign never sounded so good.

After it went to no.1 in 1992, you were hard-pressed to walk into any honky-tonk and not see someone line dancing to this absolute hit. - KS

20
Vince Gill - When Love Finds You - Album Cover

MCA Records | 1994

Vince Gill - Go Rest High On That Mountain

It’s no accident that Vince Gill was inspired to write ‘Go Rest High on That Mountain’ after the death of Keith Whitley.

The song is one of the country genre’s most profound musical answers to death, with backing vocals from Ricky Skaggs and Patty Loveless that further evoke its spirituality.

Gill went on to perform it at the funeral services of the legendary likes of George Jones and Charlie Daniels. - CL

19
Mary Chapin Carpenter - Come On Come On - Album Cover

Sony BMG Music Entertainment | 1992

Mary Chapin Carpenter - He Thinks He'll Keep Her

There’s nothing in the least bit lite about this 90s feminist country classic.

Mary Chapin Carpenter picks apart the drudgery of housework and unequal parental responsibilities in an unhappy 15-year marriage, which she eventually leaves, only to find that her job opportunities outside of the home are limited by the patriarchy too. - JO

18
The Judds - Love Can Build A Bridge - Album Cover

Curb Records | 1990

The Judds - Love Can Build A Bridge

The title track of the Judds’ last full studio album, ‘Love Can Build a Bridge’ serves as a last word of sorts from the hitmaking mother-daughter duo.

An epic testimony to the power of human connection, the song was a fitting sign-off, as poignant as any of the duo’s more upbeat, radio-friendly hits. - CL

17
Trisha Yearwood - Thinkin About You - Album Cover

MCA Nashville | 1995

Trisha Yearwood - XXX's and OOO's (An American Girl)

Ever since releasing ‘She’s in Love with the Boy’ as her first hit single, Trisha Yearwood has proven her extraordinary talent for capturing the imagination of a young girl on the precipice of adulthood.

Nowhere is that more evident than on ‘XXXs and OOOs’, a coming-of-age narrative that continues to fit right into the stories of young women everywhere today. - CL

16
Travis Tritt - Trouble - Album Cover

Warner Records | 1992

Travis Tritt - T-R-O-U-B-L-E

This song feels like a tornado coming at you full speed.

From the driving guitar to the fiddle, 'T-R-O-U-B-L-E' was (and still is) the song you want playing in your car as you race down the road on the way to the big field party. - KS

15
Brooks & Dunn - Brand New Man Album Cover

Arista | 1991

Brooks & Dunn - Boot Scootin' Boogie

Brooks & Dunn’s signature line dance track, ‘Boot Scootin’ Boogie’ featured on the duo’s 1991 debut album, Brand New Man.

Although first recorded by Asleep at the Wheel, Brooks & Dunn saw great success with their version. The 32 counts of footwork choreographed alongside this single quickly became a dance phenomenon across honky tonks worldwide. - MO

14
Artwork - Reba - Rumor Has It

1990 | MCA

Reba McEntire - Fancy

Originally written and recorded by Bobbie Gentry, Reba McEntire really made this song her own in 1990. Now it’s become the iconic encore of her shows.

Due to its references to prostitution, it was a slightly edgy song for both Gentry in the 60s and McEntire in the 90s.

McEntire’s version surpassed the original’s success on the country charts. - ZH

13
Joe Diffie - Greatest Hits - Album Cover

Sony BMG Music Entertainment | 1990, 1992, 1993, 1994, 1995, 1998

Joe Diffie - Pickup Man

Joe Diffie finds the double meaning of the phrase “pick up” and proceeds to drive all around town with it on this hit.

The twanging truck anthem predated bro-country’s predilection for tailgates by a good 15 years, as he ran through all the incidental benefits of an eight-foot flatbed lifestyle. - JO

12
Album - Deana Carter - Did I Shave My Legs For This?

Patriot Records | 1995 / Capitol Records | 1996

Deana Carter - Strawberry Wine

It’s hard not to love this summery coming-of-age track, inspired by songwriter Matraca Berg’s own experiences as a teenager.

From the pedal steel that dominates the production to Carter’s wispy vocals, this 1997 CMA Song of the Year has the power to transport you to another time. - ZH

11
Tim McGraw - All I Want - Album Cover

Curb Records Inc | 1995

Tim McGraw - I Like It, I Love It

Clearly, Tim McGraw is down to do anything to impress his girl (if you’ve ever been to a county fair and tried to win a stuffed teddy bear, you understand his dedication).

There were few songs in the 90s that had a better hook than this one. It’s not a surprise that it’s now the official song for the Nashville Predators NHL Hockey team - it blares out of the speakers every time the team score. - KS

10
Alan Jackson - A Lot About Livin' - Album Cover

Arista Records | 1992

Alan Jackson - Chattahoochee

AJ wolfs down a burger and a snow cone and drops his date off early so he can head down to the riverbank to shoot cans and pull handbrake turns with his buddies.

He unexpectedly turned 90s summer wear on its head by water skiing in just cowboy boots and a life jacket in the video. We love to see it. - JO

9
Tracy Byrd - No Ordinary Man - Album Cover

MCA Records | 1994

Tracy Byrd - Watermelon Crawl

Released in 1994 as the second single off No Ordinary Man, Tracy Byrd's stone-cold party starter 'Watermelon Crawl' is a line dance anthem.

Ever fulfilling his role of responsibility, the mayor of a small town in Georgia encourages its people (who are all having a great time knocking back watermelon wine at the local festival) to "obey the law / if you drink, don't drive / do the watermelon crawl".

Sounds like our kinda town. - Ciara Bains

8
LeAnn Rimes - How Do I Live - Single Cover

Curb Records | 1997

LeAnn Rimes - How Do I Live

Penned by Diane Warren, ‘How Do I Live’ was originally written for LeAnn Rimes - although it could also easily be described as a Trisha Yearwood song.

Both women released versions of the single on the exact same day, while both performances were nominated in the same Grammys category (Yearwood’s version won).

The song is positive proof that great material in the hands of great artists can easily stand the test of time. - CL

7
Shania Twain - Come On Over - Album Cover

UMG Recordings | 1997

Shania Twain - Man! I Feel Like A Woman

There are two kinds of people in the world: those who get goosebumps when they hear the phrase “Let’s go girls” and liars.

Twain’s loud-and-proud single demolishes any notion that women - and female artists in country - need to be quiet or subtle.

The song, like Twain herself, is unabashedly true to its own quirky personality, equal parts goofy and anthemic. - CL

6
The Chicks - Wide Open Spaces - Album cover

Columbia Records | 1997, 1998

The Chicks - Wide Open Spaces

The Chicks painted a picture of what every girl wants in life: the room to make a big mistake.

This massive hit ended up in the hands of the trio by way of Natalie Maines’ father, Lloyd Maines. He produced an album by alt-country band The Groobees, who recorded ‘Wide Open Spaces’ for it.

When the Chicks performed their version of the song in concert for the first time, it’s safe to say the fans loved it. - KS

5
Garth Brooks - No Fences - Album Cover

Capitol Records Nashville | 1990

Garth Brooks - Friends In Low Places

Turn up on any night of the week in any bar along Nashville’s Broadway and someone will be singing this 90s classic.

Garth reflects on turning up drunk and inappropriately dressed to an ex-girlfriend’s fancy black tie event; behaving like an absolute muppet by toasting her new boyfriend and just generally embarrassing himself.

We’ve all been there. - JO

4
Iris DeMent - Infamous Angel - Album Cover

Yep Roc Records | 1993

Iris DeMent - Let The Mystery Be

Iris Dement may be best known for ‘Our Town’ - or her duet work with John Prine - but it’s another selection from her 1992 debut, Infamous Angel, that has best kept its replay value over the years.

That’s ‘Let the Mystery Be’, a meditation on life’s sweet unknowns and a masterclass in simplicity. - CL

3
Faith Hill - Faith

Warner | 1998

Faith Hill - This Kiss

The first single from Hill’s third album turned into one of her biggest crossover hits and even snagged two Grammy nominations.

What we all really remember, though, is the video. It was whimsical and full of fantasy; Faith jumping from flower to flower and swinging on a giant nectarine. Long live 90s music videos. - KS

2
The Chicks - Fly - Album Cover

Colombia Records | 1999

The Chicks - Goodbye Earl

Shining a light on revenge after abuse, ‘Good Bye Earl’ lays bare shocking domestic violence.

Sending shivers down the spine with its astonishingly sweet harmonies, it’s still hard to fathom that this was written by a man, Dennis Linde. - HJ

1
Martina McBride - The Way That I Am - Album Cover

Sony Music | 1993

Martina McBride - Independence Day

A good song is one you come back to again and again and never tire of. A great song is that, but one that also makes you feel something; each and every time its layers slowly revealing themselves anew.

‘Independence Day’ is undoubtedly a great song. With raw, honest songwriting from Grethen Peters and unmatched vocals from Martina McBride, here at Holler HQ it’s our unanimous pick as the no.1 song of the 90s.

Sure, you can scream along with the chorus without really understanding the gravity of the song - as is evident from the many radio stations who programme it heavily every 4th of July -but once you tune in to the story it’s telling, it’s a shock to the system.

Whether you’ve been through what ‘Independence Day’ is addressing or not, it’s a song that anyone who’s ever gotten out of a bad situation, finally free to sing at the top of their lungs, can relate to. Let freedom ring indeed! - Baylen Leonard

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