50 Essential '90s Country Songs 

It just doesn't get better than '90s country music. The decade saw the rise of superstars like Faith Hill, Shania Twain, Tim McGraw, Kenny Chesney and many more. It brought us line dancing, from the "Boot Scootin' Boogie" to the "Watermelon Crawl," gave us some unforgettable fashion and hairstyles, and, most importantly, some seriously great songs.

In recent years, younger generations have latched onto '90s country and brought popular tunes, such as Brooks & Dunn's "Neon Moon," back into the spotlight. And some of today's biggest stars love to hat tip the decade that made them fall in love with country music. Yes, there's no lack of nostalgia for '90s country. So we rounded up the most essential country songs of the decade, including songs about first love ("Strawberry Wine"), leaving home ("Wide Open Spaces") and letting loose ("Man! I Feel Like a Woman"). So put on your acid wash Levi's and your Wrangler Brushpopper shirt and check out our roundup of 50 of the best and most memorable country songs of the '90s.

 "Check Yes or No" (Strait Out of the Box, 1995)

George Strait, the crowned king of country music, was also one of the kings of '90s country along with Garth Brooks. Of course, he started his career in the 1980s with hits such as "Amarillo By Morning," "Ocean Front Property" and more, but his '90s hits can't be ignored. There's the 1996 hit "Blue Clear Sky" as well as "Carrying Your Love With Me," but one of the Texas artist's biggest songs from the '90s is "Check Yes or No." In this timeless love song, Strait sings of a third grade boy who gets a girl's attention with a note asking, "Do you love me, do you want to be my friend?" The girl then has to check yes or no to answer the boy's question. As one could predict, that third grade couple go on to become husband and wife and live a happily-ever-after life together. — Grace Lenehan Vaughn

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 "Chattahoochee" (A Lot About Livin' (And a Little 'Bout Love) 1992), Alan Jackson

Alan Jackson brought undeniable swagger to the country music of the '90s, breaking onto the scene as a 31-year-old singer with his 1990 hit, "Here In The Real World." Other '90s hits of his include "Don't Rock The Jukebox" and "Livin' On Love," but few are as memorable as his 1993 song, "Chattahoochee." In this energetic, fiddle-filled tune, Jackson reflects on youthful summer days on the Chattahoochee River in Georgia. The song is full of nostalgic images of days spent learning "A lot about livin' and a little 'bout love." One can also never forget the music video, which features Jackson waterskiing in jeans. This '90s tune is another that has stood the test of time. — Grace Lenehan Vaughn

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 "Don't Take The Girl" (Not a Moment Too Soon, 1994) Tim McGraw

Like Garth Brooks, Alan Jackson and others, Tim McGraw is an artist whose star rose the 1990s and is still releasing hit songs today. Some of his memorable '90s songs include "I Like It, I Love It" and "Something Like That," but one of his biggest hits was "Don't Take The Girl," released in 1994. In this classic story song, McGraw sings of a father and son who go on a fishing trip and, to the son's chagrin, bring along a neighbor girl. As the years go on, however, the young boy and girl begin to fall for one another, and the song tells the powerful and heartbreaking story of their love. Like other tunes on this list, this '90s song is one that won't soon be forgotten. — Grace Lenehan Vaughn

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"She's In Love With The Boy" (Trisha Yearwood, 1991) Trisha Yearwood

Another top country artist to who made her start in the '90s is Trisha Yearwood, who came out of the gate in 1991 with her No. 1 song, "She's in Love With the Boy." In this song, Yearwood tells the story of a rebellious young woman who falls in love with a boy who doesn't meet her father's standards, but their love transcends all boundaries. Yearwood went on to release more classic hits, including "Walkaway Joe," "XXX's and OOO's (An American Girl)" and more, but "She's in Love With the Boy" continues to be one of her most essential tunes. — Grace Lenehan Vaughn

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"How Do I Live" (You Light Up My Life: Inspirational Songs, 1997) LeAnn Rimes

LeAnn Rimes first debuted on the country scene with the classic-country inspired "Blue," which she recorded when she was 13-years-old. The next year, when she was 14, she broke out with her crossover hit, "How Do I Live." Rimes originally recorded the tune for the motion picture, Con Air, but after movie producers decided she was too young to be singing a song of such subject matter, they turned to Trisha Yearwood to record it instead. However, Rimes' version was still released, and it became a worldwide hit. The soaring love song landed at No. 1 on the Adult Contemporary chart and peaked at No. 2 on the Billboard Hot 100 for five weeks. It also set a record for being on the Hot 100 chart for 69 weeks. — Grace Lenehan Vaughn

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"Boot Scootin' Boogie" (Brand New Man, 1991) Brooks & Dunn

It's not '90s country without Brooks & Dunn, and their swinging hit, "Boot Scootin' Boogie," made waves during the decade. The song, released in 1992, is a simple ode to Western line dancing, and it is credited with contributing to a new interest in the dance style. "Boot Scootin' Boogie" is classic Brooks & Dunn, and in addition to landing at No. 1 on the Country charts, it was their first single to cross over to the Billboard Hot 100, landing at No. 50. — Grace Lenehan Vaughn

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 "This Kiss" (Faith, 1998) Faith Hill

A list about '90s country is not complete without a song from '90s country-pop queen, Faith Hill. Hill debuted in the early '90s with songs such as "Wild One" before finding international success with more pop-influenced songs. Her 1998 anthem, "This Kiss," was one of her most popular among those, landing at No. 1 on the Country charts, No. 7 on the Hot 100 and No. 3 on the Top 40 charts. It also charted on the US Adult Contemporary chart and US Adult Pop chart, in addition to being nominated for a Grammy in 1999. — Grace Lenehan Vaughn

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"Watermelon Crawl" (No Ordinary Man, 1994), Tracy Byrd

It's tempting to lump Tracy Byrd's signature song in with "Achy Breaky Heart," "Pickup Man" and other lighter-hearted '90s classics that remind us that country music isn't always serious business. There's a not-so-subtle difference with "Watermelon Crawl," though— Byrd pleads with fans in bars and at festivals to remember that the dangers of drinking and driving are no laughing matter. — Bobby Moore

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"She Thinks My Tractor's Sexy" (Everywhere We Go, 1999),  Kenny Chesney

Kenny Chesney capped off the decade in which he emerged as an elite singer of songs about living life to its fullest with something that's way more jovial. Jim Collins, co-writer of the much-more-sincere Chesney classics "The Good Stuff" and "Everybody Wants to Go to Heaven," penned this one with fellow heart-song carpenter Paul Overstreet (The Judds' "Love Can Build a Bridge," George Strait's "Forever and Ever, Amen"). Once Chesney got ahold of it, the delightful absurdity of Johnny Cash's "A Boy Named Sue" got a new coat of paint— or Walker Hayes' "Fancy Like" got prophesied, depending on your perspective. — Bobby Moore

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"Pickup Man" (Third Rock From the Sun, 1994) Joe Diffie

Modern-day honky-tonk genius Joe Diffie made this rural living parody a four-week No. 1 in Dec. 1994 and Jan. 1995. It's more than a string of memorable one-liners about trucks. There's a second layer that mocks would-be small-town pickup artists who view nice wheels as the key to scoring a little black book full of pager numbers. — Bobby Moore

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"Bye-Bye" (I'm Alright, 1998) Jo Dee Messina

Jo Dee Messina was an incredibly important fixture in '90s country who brought an upbeat layer to country radio with her songs. Her debut single "Heads Carolina, Tails California" has been brought back into the spotlight as of late thanks to Cole Swindell's "She Had Me at Heads Carolina," but she had many other memorable hits throughout her career. One of those is the sassy "Bye Bye" released in 1998 from her I'm Alright album. In this song, Messina rebukes a potential love interest who took a little bit too long to decide if he wanted to be with her. Due to his indecision, Messina makes the choice for him and cuts him loose. The song serves as Messina's goodbye to this man, and she sure doesn't regret her decision. This cheery tune was written by Rory Bourke and fellow artist Phil Vassar, and it became her first-ever No. 1. — Grace Lenehan Vaughn 

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"Fast As You" (This Time, 1993) Dwight Yoakam

In the '80s, Dwight Yoakam made Memphis rockabilly and Bakersfield-style country cool to listeners more accustomed to punk and new wave. The singer, songwriter and actor remained retro chic in the '90s as the rest of country music caught up with him, as proven by the short-term success and lingering legend of 1993 album This Time and this single that's still his most recent Top 10 country hit. — Bobby Moore

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"Tempted" (Tempted, 1991) Marty Stuart

A walking history book whose first bosses were Lester Flatt and Johnny Cash, Marty Stuart met the '90s country moment with music informed by his love of the genre's past and childhood hours spent listening to early rock 'n' roll. For instance, this Top 5 single from 1991 suited modern listener's tastes yet incorporated elements of legends ranging from Roy Acuff and Roy Orbison. — Bobby Moore

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"It's Your Love" (Everywhere, 1997) Tim McGraw, Faith Hill

When Tim McGraw and Faith Hill get together to record a song, magic undeniably follows, and their first-ever duet, "It's Your Love," proves this. In this classic love song from the husband-wife duo, they sing about how the love they feel in a relationship has has changed them forever. The song has everything one could want from a '90s love song: passionate lyrics, ultra-country instrumentation and a soaring chorus.  The song was a huge hit for the artists, landing at the No. 1 spot after just five weeks and staying three for six weeks. It also landed at No. 7 on the Billboard Hot 100, becoming a first for both artists. The song won awards at both the ACMs and CMAs, and it has gone down in history as one of the couple's most classic duets. — Grace Lenehan Vaughn 

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"Amazed" (Lonely Grill, 1999) Lonestar

If there was a competition for the best country love song of the '90s, Lonestar's "Amazed" would certainly be a contender. This tune was released in 1999 from the band's Lonely Grill album, and it became one of their biggest hits that still holds up today. On the whole, the tune is a passionate love song in which lead singer Richie McDonald sings about all the things he loves about his partner and his desire to stay with her forever. Between the sweet lyrics and the song's sweeping melody and instrumentation, it's not hard to see why this power ballad had such an effect on listeners. The song spent a total of eight weeks atop the Country charts, and a pop remix crossed over and topped the Hot 100 chart. The song has since been covered by a slew of artists, including Boyz II Men. — Grace Lenehan Vaughn 

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"Sold (The Grundy County Auction Incident)" (John Michael Montgomery, 1995) John Michael Montgomery

When he wasn't making listeners cry with some of the most tender-hearted material of the '90s, John Michael Montgomery matched the frenetic energy we'd soon hear from his brother, Eddie Montgomery of Montgomery Gentry. The shining example of this is "Sold (the Grundy Country Auction Incident)," a rapid-fire and smile-inducing No. 1 that's chock-full of tongue-twisting lyrics about lust at first sight. It's one of five decade-defining hits from John Michael's self-titled 1995 album. — Bobby Moore

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"Every Light in the House" (Dreamin' Out Loud, 1996) Trace Adkins

Trace Adkins began his career in the mid-'90s, and it was his second single, "Every Light in the House," that truly put his career into high gear. Released in August 1996 from his Dreamin' Out Loud album, this slow heartbreak tune finds Adkins singing from the perspective of a man dealing with the end of a relationship. His love interest left him, but he holds out hope that she'll come back, and just in case she does, he leaves every light on in the house for her return. This wistful tune made a mark on country listeners at the time, and it landed at No. 3 on the charts, his highest charting song at that time. It also paved the way for more hits to come, such as "This Ain't No Thinkin' Thing," "I Left Something Turned On at Home" and more. — Grace Lenehan Vaughn 

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"Meet in the Middle" (Diamond Rio, 1991) Diamond Rio

In the '80s, Alabama cleared a path for self-contained country bands, from pop-rockers turned contemporary hitmakers Exile to current awards show regulars Old Dominion. Diamond Rio benefited, as well, when "Meet in the Middle" became the first debut single by a band to reach No. 1 on the Billboard Hot Country Songs chart. Undercurrents of bluegrass harmonies and instrumentation sweetened a showpiece of the then-current Nashville sound from a group that'd impact the mainstream into the new millennium. — Bobby Moore

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"Next to You, Next to Me" (Extra Mile, 1990) Shenandoah

Shenandoah made a big impact on country music in the 1980s and '90s, and one of its many hits was "Next to You, Next to Me," released in 1990. The tune was written by Robert Ellis Orrall and Curtis Wright and served as the lead-off single from the album Extra Mile. With the band's classic bluegrass-influenced country instrumentation, its members sing a lighthearted love song about simply being next to the person you love. The song details some of the sweet and simple moments that happen between loved ones, such as riding in a truck together, and its lyrics conclude that those simple things are all one needs in life. The song landed at the No. 1 spot and stayed there for three weeks, becoming one of their biggest hits. — Grace Lenehan Vaughn 

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"Here's a Quarter (Call Someone Who Cares)" (It's All About to Change, 1991)  Travis Tritt

Travis Tritt sarcastically takes down someone on the wrong end of a breakup with his most iconic single. Its Top 5 popularity had a downside once fans started pelting the singer with quarters during live shows. Workplace hazards aside, the Georgia native benefitted greatly from a song that would be evergreen if pay phones weren't obsolete. — Bobby Moore

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"The Fool" (Lee Ann Womack, 1997) Lee Ann Womack

Lee Ann Womack broke a million hearts with this tale of a woman having a heart to heart with her love's old flame. Not unlike Dolly Parton's "Jolene," Womack's plea to the other woman isn't filled with vitriol. Rather, it's a heartfelt barstool conversation between two women with likely more than a man in common. "You don't love him and that's a fact/ Girl, I've seen you around," Womack sings. "But you hold his heart in the palm of your hand/ And it's breaking mine in two." — Bobbie Jean Sawyer

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"Breathe" (Breathe, 1999), Faith Hill

As the millennium approached, Faith Hill was a full-fledged country-pop crossover superstar. Never was that more clear than with the release of "Breathe," a sultry, chart-topping ballad penned by Stephanie Bentley and Holly Lamar. Hill's powerhouse voice blended with background vocals from Dolly Parton made the song one of the most memorable songs of the '90s — and one of the genre's most enduring love songs, even over 20 years later. — Bobbie Jean Sawyer

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"Love Can Build a Bridge" (Love Can Build a Bridge, 1990) The Judds

One of most meaningful songs of the era, "Love Can Build a Bridge" served as a goodbye to fans when co-writer Naomi Judd retired for the first time following a dire Hepatitis-C diagnosis. Before Garth Brooks shattered misconceptions about country artists' social views with "We Shall Be Free," Naomi and her daughter Wynonna preached forgiveness and unity — a message that's remained evergreen in a society that's no less fractured than it was over 30 years ago. — Bobby Moore

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"XXX's and OOO's (An American Girl)" (Thinkin' About You, 1995) Trisha Yearwood

Trisha Yearwood was one of the biggest voices of the '90s. She, along with the likes of Martina McBride, Faith Hill and others, made up the successful group of female artists that dominated the genre during the decade. One of Yearwood's most memorable songs from the era is "XXX's and OOO's," released from her Thinkin' About You album in 1994. Similar to her classic tune "She's In Love With the Boy," this song features bouncy, upbeat instrumentation as Yearwood tells a female-centered story. The song tells the story of a working mother trying to do it all. It also references the change of culture and gender roles through the years, as she sings about having a picture of her mother "in heels and pearls," but she's trying to make it in her "daddy's world." The tune became Yearwood's second No. 1 hit and set the scene for more success to come. — Grace Lenehan Vaughn 

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"Cowboy Take Me Away" (Fly, 1999) The Chicks

The Chicks delivered a love song for the ages with "Cowboy Take Me Away," a soaring ode to riding off into the sunset with the one you love. The tune was penned by Marcus Hummon and trio member Martie Maguire, who was inspired to write the song for her sister and bandmate Emily Strayer's marriage to Texas singer-songwriter Charlie Robison. Over 20 years later, the song still resonates with listeners of all walks of life. Whether or not you ever get to lay on that pillow of bluebonnets in a blanket made of stars with your sweetheart, the dream of being all alone with your soulmate, free from the distractions of daily life, is enough to make anyone's heart skip a beat.  — Bobbie Jean Sawyer

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"I Love the Way You Love Me" (Life's a Dance, 1992) John Michael Montgomery

John Michael Montgomery was the reigning king of country love songs in the '90s, with "I Swear" burning up the pop charts with R&B group All-4-One's version. But before the crossover success of that heartfelt ballad, Montgomery struck gold with his first chart-topper, "I Love the Way You Love Me." Written by Victoria Shaw and Chuck Cannon, who was inspired by his wife, country singer-songwriter Lari White, the song is a perfect example of why specificity is universal. The ballad eschews cliche phrases in favor of praising the idiosyncrasies that make a partner irresistible, from the way she rolls her eyes to the way she cries over her favorite films. — Bobbie Jean Sawyer

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"Something in Red" (Something in Red, 1991), Lorrie Morgan

Though she recorded top-flight material back in the '70s and found her mainstream footing as part of country's Class of '89, Morgan's halcyon days stretched across the '90s. Written and first recorded the year prior by lesser-known country artist Angela Kaset, the cinematic title track of Morgan's 1992 album painted her as a top-flight songteller on par with Kathy Mattea, Hal Ketchum and other respected peers. — Bobby Moore

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"God Blessed Texas" (Big Time, 1993) Little Texas

Anyone who's ever lived in Texas knows the immense pride Texans take in their home state. The appropriately named Little Texas captured that feeling with the anthemic "God Blessed Texas," a rousing ode to the Lone Star State's landscape and culture and, of course, Texas women. The song can still be heard state-wide, including at Dallas Cowboys games, proving that just like Lone Star beer, barbecue and Whataburger, loving Texas will never go out of style. — Bobbie Jean Sawyer

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"I Cross My Heart" (Pure Country, 1992) George Strait

This committed love song by George Strait isn't just one of the most essential '90s country songs, it's also one of Strait's most memorable songs. "I Cross My Heart" was released in September 1992, and it was originally record for the movie, Pure Country, which starred the singer. The song was included on the movie's soundtrack, and not only did it serve its purpose in the story of the film, but it became a major hit. In the song, Strait sings of his undying love for a partner, promising to be there for her forever. The lyrics are unmistakable, as he croons, "I cross my heart and promise to give all I've got to give to make all your dreams come true / In all the world, you'll never find a love as true as mine." The song has since been certified 2x Platinum. — Grace Lenehan Vaughn 

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"Someday Soon" (Aces, 1991) Suzy Bogguss

Though this Ian Tyson-penned song was already a western standard by the time Suzy Bogguss recorded it for her album Aces, the Illinois-born artist introduced "Someday Soon" to a whole new generation — at least those who hadn't already heard Judy Collins' version from their folkie parents. Whatever your introduction, Bogguss perfectly captures a lovelorn young woman's plea for that Blue Norther to send her rodeo cowboy back to her arms. — Bobbie Jean Sawyer

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"On a Good Night" (On a Good Night, 1996) Wade Hayes

Wade Hayes was among the mid-'90s crop of country artists following in the boot steps of modern traditionalists such as Alan Jackson, Clint Black and George Strait, whom Hayes' name-drops in "On a Good Night," the lead single from his 1996 album of the same name. The uptempo track still stands as one of the best party songs of the '90s, with Hayes playing the part of a rabble rouser in search of a good time and a "brown hair, blue eyes, once in a lifetime countrified kind of girl." — Bobbie Jean Sawyer

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"Loving Blind" (Put Yourself in My Shoes, 1990),  Clint Black

Clint Black is another artist who saw great success throughout the 1990s, and his 1991 single, "Loving Blind," aided in that success. Released as the second single from his sophomore album, the tune finds Black reflecting on the journey of life and love. He sings from the perspective of a man who's been through his share of heartbreak, but by the end of the song, it doesn't seem to bother him anymore and he moves on with his life. The song was written solely by Black, and it became the fifth No. 1 of his career, spending two weeks atop the charts. It also set the scene for many more hit songs from Black in the 1990s and beyond. — Grace Lenehan Vaughn 

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"Blue Clear Sky," George Strait

George Strait was responsible for releasing many of the essential country songs of the '90s, and one of them was the lighthearted "Blue Clear Sky" from 1996. In this song, which is filled with twangy steel guitar, Strait sings about a love that seemed to fall right out of the sky — when he least expected it. The tune was penned by Bob DiPiero, John Jarrard and Mark D. Sanders, and although Strait liked the song when he heard it, he originally thought he hook should be changed to "clear blue sky." However, when DiPiero explained that he got the idea from a line in the classic Tom Hanks film Forrest Gump, they decided to keep the lyrics the way they were. The phrasing of the title didn't seem to bother listeners, and the tune became a No. 1 hit for Strait. — Grace Lenehan Vaughn 

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"Achy Breaky Heart" (Some Gave All, 1992) Billy Ray Cyrus

Like most inescapable hits before or since it, "Achy Breaky Heart" faced pushback for lacking lyrical depth. The authenticity police were predictably and lazily out in full force — though country music has overlapped with pop for 100 years now. In reality, there's always room for mindless fun, and not everything needs to be a Guy Clark-caliber story song to connect with listeners or maintain staying power. — Bobby Moore

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"I Like It, I Love It" (All I Want, 1995) Tim McGraw

A signature tune of an artist who's still commercially relevant nearly 30 years later, McGraw added to the near-endless '90s country party playlist with this ear candy that's yet to lose its flavor. Two things timestamp it for those of us who vividly remember the '90s: fiery fiddling that linked a crossover-friendly revolution to country's past and a reference to when Braves games on the Superstation were appointment viewing. — Bobby Moore

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"Any Man of Mine" (The Woman in Me, 1995), Shania Twain

Shania Twain came in like a hurricane with this boot-stomping barn burner from her breakout album The Woman in Me. Clad in denim-on-denim in the song's equally iconic video, Twain lays out her demands for a fulfilling relationship, which includes being okay when she has a bad hair day (fair), pretending to like her cooking and being prepared to "shimmy shake" and "make the earth quake." — Bobbie Jean Sawyer

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"Should've Been a Cowboy" (Toby Keith, 1993) Toby Keith

Many first heard Toby Keith's commanding baritone delivery via his self-penned debut single. Nostalgia for western films and TV shows still draws in listeners, as do those stunning background harmonies. What's aged this one gracefully, though, is an underlying theme: for most of us, our childhood visions of adulthood don't line up with the realities of day-to-day life. — Bobby Moore

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"Maybe It Was Memphis" (Put Yourself in My Place, 1990) Pam Tillis

Perhaps no '90s track better exemplified southern romance that Pam Tillis' "Maybe it Was Memphis." You can practically feel the humidity of a Tennessee night and hear the katydids singing as Tillis tells of a Tennessee Williams and William Faulkner-worthy love affair. Not unlike "Strawberry Wine," which would come along a few years down the road, the song is narrated by a young woman who still finds herself thinking about her whirlwind romance with a "lonely boy far from home." — Bobbie Jean Sawyer

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"Blame It On Your Heart" (Only What I Feel, 1993)  Patty Loveless

Patty Loveless racked up a string of unforgettable hits in the '90s but there was no better kiss-off to an unworthy ex than the Harlan Howard and Kostas-penned "Blame It On Your Heart." Any breakup is aided by blasting this tune and singing along with Loveless' description of a "lying, cheating, cold, dead beatin', two timin', double dealin' mean, mistreatin', lovin' heart." — Bobbie Jean Sawyer

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"Man! I Feel Like A Woman" (Come On Over, 1997), Shania Twain

Many male country singers dominated the 1990s, but the decade also saw the rise of female artists who continued to take the genre to new heights. When thinking about these powerful female artists, Shania Twain is top of mind. With crossover hit singles such as "You're Still The One," "Any Man Of Mine" and "That Don't Impress Me Much," Twain became one of the bestselling artist of the decade (and of all time). Her 1999 song, "Man! I Feel Like A Woman," is especially one that has gone down in the history books. The high-powered, female anthem is still heard in popular culture today, and the song's opening line, "Let's go girls," has had its own life as a meme. — Grace Lenehan Vaughn

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"Friends In Low Places" (No Fences, 1990) Garth Brooks

Garth Brooks undoubtedly ruled the '90s. It was the decade he broke through with singles such as "The Dance," "The Thunder Rolls" and more, leading him to becoming the world-renowned, multi-platinum selling singer he is today. While those songs are certainly notable, one of his most memorable tunes from the '90s is "Friends In Low Places." In this song, which can start a sing-along at a concert or a honky-tonk, the character portrayed by Books confronts an ex-girlfriend and her swanky new man in an epic fashion. The song has since become a country anthem for anyone with "friends in low places." — Grace Lenehan Vaughn

 

"Goodbye Earl" (Fly, 1999) The Chicks

The Chicks delivered on of the decade's most stirring story songs with "Goodbye Earl," a Thelma and Louise-esque saga about two best friends, Mary Ann and Wanda, who slip a little something (allegedly) into Wanda's abusive husband Earl's black eyed peas. They then proceed to wrap him in a tarp, throw him in a lake and open a roadside stand that sells Tennessee ham and strawberry jam. And no, they don't lose any sleep at night over old Earl. This song, however, written by the great Dennis Linde, still gets crowds going over 20 years later.  — Bobbie Jean Sawyer

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"Does He Love You" (Greatest Hits Vol. 2, 1993) Reba McEntire, Linda Davis

Reba McEntire and Linda Davis' classic duet "Does He Love You" is an essential song of the '90s that made an impact outside of country music, and that impact is still felt today. The tune finds McEntire and Davis singing back and forth as two downhearted women who are in love with the same man. The song was written by Sandy Knox and Billy Stritch, and it was initially pitched to Barbara Mandrell and Liza Minelli before it landed in McEntire's hands. McEntire chose her then-backup singer, Davis, to sing the tune with her against the advice of her record label, who would have preferred Wynonna Judd or Trisha Yearwood. In fact, McEntire did ask Judd if she'd like to collaborate on the track, but when she didn't hear back, she went ahead with Davis. The song became a major Grammy-winning hit, and it has been covered by artists outside of country music, such as Minelli and Donna Summer. The song continues to live on today, and McEntire has performed it many times throughout the years with duet partners like Kelly Clarkson and Dolly Parton. — Grace Lenehan Vaughn 

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"That Don't Impress Me Much" (Come On Over, 1997) Shania Twain

This classic Shania Twain song was released during the height of the singer's dominance in 1990s pop country. "That Don't Impress Me Much" is the perfect example of Twain's sassy songwriting and singing style, as explains her high standards for a man. The song features many humorous moments and even a shoutout (albeit, not the most positive one) to Hollywood's top guy at the time, Brad Pitt. The song became one of her biggest hits, crossing over to pop radio and topping charts all over the world. — Grace Lenehan Vaughn 

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"Fancy" (Rumor Has It, 1990) Reba McEntire

Though it stalled at No. 8 on the Billboard Hot Country Songs chart, "Fancy" is among the first songs that comes to mind when you mention Reba McEntire to a child of the '90s. It was a minor country and pop hit in 1970 for its writer, Bobbie Gentry, who'd willfully disappeared from the public eye in 1982. By including it on 1990's Rumor Has It, McEntire used her platform to point new ears to Gentry's storytelling brilliance. — Bobby Moore

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 "Strawberry Wine" (Did I Shave My Legs for This, 1996) Deana Carter

Deana Carter forever made her name in country music with her breakout album Did I Shave My Legs For This? and hit single "Strawberry Wine." In this wistful tune that tells a coming-of-age story, Carter recalls a small town love affair from her teenage years, and although the relationship ended, she remembers it bittersweetly, just like the strawberry wine they drank. In addition to reaching the No. 1 spot on the charts, the tune won Song of the Year at the 1997 CMA Awards. — Grace Lenehan Vaughn

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"Neon Moon" (Brand New Man, 1991) Brooks and Dunn

Brooks & Dunn updated the classic country drinking-to-forget song at a time when Hank Williams Jr.'s 1989 revival of his dad's "There's a Tear in My Beer" was still stuck in radio listeners' heads. In the 21st century, "Neon Moon" is no less of a standard than any other sympathetic take on emotionally-wounded barflies. As a matter of fact, it's as synonymous nowadays with the '90s country boom as the duo's line-dancing trendsetter "Boot Scootin' Boogie." — Bobby Moore

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"Wide Open Spaces" (Wide Open Spaces, 1998), The Chicks

Although The Chicks established themselves as solid group with the first two singles of their career, it was their third release, "Wide Open Spaces," which propelled them to the level of fame they would become known for the '90s and early 2000s. "Wide Open  Spaces" is a feel-good tune that pairs airy, acoustic instrumentation with a free-spirited story about a woman looking for a new frontier. The song became the group's second No. 1 hit and it has since been certified 2x Platinum. The tune also established The Chicks as a country trio with a knack for singing relatable songs that feature traditionally leaning country instrumentation with nods to Western and Southern lifestyle. — Grace Lenehan Vaughn 

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"Independence Day" (The Way That I Am, 1993) Martina McBride

Penned by first-rate storyteller Gretchen Peters, Martina McBride's chill-inducing "Independence Day" was one of the most debated and misunderstood songs of the '90s. It's often been mistaken as a patriotic or political anthem, with listeners either misunderstanding or willingly ignoring the song's story about an abused woman. Some radio stations even refused to play it. ("They were like, 'I don't think this needs to be on my radio station," McBride told Rolling Stone. "I don't think people need to be hearing this'...And I'm like, 'Well, it's on your news every hour. This is topical.'") But no stubborn radio programmer or misguided use of the track on talk radio could ever take away from the power of the song or McBride's soaring voice. — Bobbie Jean Sawyer

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"Go Rest High On That Mountain" (When Love Finds You, 1994), Vince Gill

Though it barely cracked the Top 15, critical success and awards show acclaim —two Grammys included— solidified Vince Gill's signature country-gospel ballad as a classic in its own time. Gill started its lyrics after the 1989 death of Keith Whitley and finished them following the 1993 passing of his older brother, Bob Gill. Fellow bluegrass talents turned country stars Ricky Skaggs and Patty Loveless chipped in on harmony vocals, amplifying the graveside service feel to one of the most powerful songs about mortality and the afterlife. — Bobby Moore

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