The 1990s marked a pivotal moment in history for country music. Over the span of ten years, the genre went through a host of changes and shifts. The first half of the decade brought a new wave of what was coined as "neo-traditional country," with artists like George Strait and Alan Jackson bringing sonic elements from the 50s and 60s to their music.

The soaring popularity of artists like Garth Brooks and Shania Twain brought new pop elements to the country scene as the 90s wore on. Female voices took hold of the country charts, with incredible music coming from artists like Reba McEntire, Patty Loveless, The Chicks, Deana Carter and LeAnn Rimes, just to name a few.

That decade also supplied some of the most memorable and widely successful duets from established artists and exciting newcomers. The romance between Faith Hill and Tim McGraw spawned a string of hit collaborations that would continue into the new millenium. Travis Tritt and Marty Stuart supplied plenty of honky tonk anthems. Garth Brooks found even more success on the charts by teaming up with Trisha Yearwood and Steve Wariner. A host of country newcomers grew their careers by teaming up and releasing tunes that caught the attention of eager new fans.

Let's take a look back at the most beloved and some often overlooked tunes from that important era. Keep reading to see our list of 90s country duets and collaborations that are worth another listen:

  • "The Heart Won't Lie"

    Reba McEntire and Vince Gill

    Released as the second single from McEntire's ninteenth studio album It's Your Call, "The Heart Won't Lie" hit No. 1 on the Billboard Hot Country chart in 1993. McEntire originally planned on recording the tune with Kenny Rogers, but their vocal ranges were just too different. Producer Tony Brown was the one who suggested giving Gill, who was originally tapped to record background vocals, a chance at singing some verses. Their voices blended perfectly, and the rest is history.

  • "When I Said I Do"

    Clint Black and Lisa Hartman Black

    Clint Black released "When I Said I Do" as the lead single off of his 1999 record D'lectrified. This sweet collaboration was Black's first single featuring his wife Lisa, a talented singer and actress in her own right. "When I Said I Do" became a crossover hit, making it to No. 1 on the Billboard Hot Country chart and No. 31 on the multi-genre Hot 100 chart.

  • "From This Moment On"

    Shania Twain and Bryan White

    "From This Moment On" was the fourth single from Shania Twain's landmark album Come On Over. The track was originally released as a duet with 90s country breakout Bryan White, who Twain repeatedly cited as one of the best voices in country music at the time. A solo version of the song was later released, further pushing the global success of the track. "From This Moment On" was one of many crossover successes for Twain, earning massive airplay on country, pop and adult contemporary radio stations.

  • "If You See Him, If You See Her"

    Reba McEntire and Brooks & Dunn

    This memorable ballad became a No. 1 hit for Reba McEntire, Ronnie Dunn and Kix Brooks in 1998. The collaboration was uniquely marketed to country listeners, becoming the title tracks for both McEntire (If You See Him) and Brooks & Dunn's (If You See Her) individual records that year.

  • "Helping Me Get Over You"

    Travis Tritt and Lari White

    Released in 1997, this collaboration from Travis Tritt and the late Lari White served as the fourth single from Tritt's fifth studio album The Restless Kind.

  • "It's Your Love"

    Tim McGraw and Faith Hill

    In 1997, "It's Your Love" was the first musical collaboration from Tim McGraw and Faith Hill to be released as a single. Featured on McGraw's acclaimed fourth studio album Everywhere, "It's Your Love" stayed at No. 1 on the Billboard Hot Country Songs for six straight weeks, marking the first time a country song had maintained that position on the chart since Waylon Jennings' "Luckenbach, Texas (Back to the Basics of Love)" took the top spot in 1977.

  • "'Til All the Lonely's Gone"

    Pam Tillis and Mel Tillis

    This moving collaboration from Pam Tillis and her father Mel Tillis is all about holding on through the pain of loneliness. Although the track didn't become a hit on the country charts, it was included on Pam's massively successful 1994 record Sweetheart’s Dance. That album produced 4 Top 10 hits, "Spilled Perfume," "In Between Dances," "When You Walk in the Room" and "Mi Vida Loca (My Crazy Life)."

  • "Brotherly Love"

    Keith Whitley and Earl Thomas Conley

    Originally recorded by Moe Bandy for his 1989 studio album Many Mansions, "Brotherly Love" is a heartwarming tune about that special, sometimes complicated relationship between male siblings. Keith Whitley and Earl Thomas Conley originally recorded their version of the song in the late 1980s, but Whitley sadly died before the pair could release their collaboration. In 1991, the duet was released on both Whitley's posthumous album Kentucky Bluebird and Conley's LP Yours Truly. The song peaked at No. 2 on Billboard's Hot Country charts and was nominated for Best Country Collaboration with Vocals at the 1992 Grammy Awards.

  • "In Another's Eyes"

    Garth Brooks and Trisha Yearwood

    In 1997, Trisha Yearwood and Garth Brooks released their romantic duet "In Another's Eyes," the second single from Yearwood's greatest hits compliation (Songbook) A Collection of Hits. Both Yearwood and Brooks had been friends and creative collaborators for years, but at the time were both married to different spouses. The track, which won a Grammy Award for Best Country Collaboration with Vocals, foreshadowed what was to come in both country artists' lives. After divorcing their previous partners, Yearwood and Brooks married in 2005.

  • "Does He Love You"

    Reba McEntire and Linda Davis

    This dramatic duet from Reba McEntire and Linda Davis became the first single from McEntire's Greatest Hits Volume 2 in 1993. The soaring song about a messy love triangle won a Grammy Award for Best Country Vocal Collaboration and a CMA Award for Vocal Event of the Year.

  • "Heart Half Empty"

    Ty Herndon and Stephanie Bentley

    This underrated duet served as Ty Herndon's third single from his acclaimed debut album What Mattered Most. Released in 1995, the collaboration elevated Herndon's already burgeoning career and helped introduce Stephanie Bentley as a solo artist prior to the release of her first record in 1996. She went on to become a successful songwriter, penning major hits including Faith Hill's "Breathe" and Martina McBride's "Concrete Angel."

  • "The Whiskey Ain't Workin'"

    Travis Tritt and Marty Stuart

    One of many stand out collaborations from Travis Tritt and Marty Stuart, "The Whiskey Ain't Workin'" was released in 1991 as third single from Tritt's sophomore album It's All About to Change. The track, which Tritt and Stuart co-wrote together, peaked at No. 2 on the country charts and earned them a Grammy Award for Best Country Collaboration with Vocals.

  • "Walkaway Joe"

    Trisha Yearwood and Don Henley

    This unforgettable ballad became a trademark song for Trisha Yearwood and cemented her as one of country music's best new voices. This collaboration with the Eagles' Don Henley was the second single from her sophomore record Hearts in Armor and made it to No. 2 on the country charts.

  • "A Bad Goodbye"

    Clint Black and Wynonna

    Clint Black and Wynonna recorded "A Bad Goodbye" not long after wrapping up their co-headlining tour in 1993. Black, who also wrote the track, chose the song as the lead single from his fourth record No Time to Kill. It became a massive success, reaching No. 2 on the Billboard Hot Country chart and earning a nomination for Vocal Event of the Year at the 1993 ACM Awards.

  • "Rockin' Years"

    Dolly Parton and Ricky Van Shelton

    Released in 1991, "Rockin' Years" served as the first single from Parton's 31st album Eagle When She Flies and Shelton's fifth record Backroads. Written by Dolly's brother, Floyd Parton, the sweet love song hit the top of the country charts in both the U.S. and Canada.

  • "Maybe Not Tonight"

    Sammy Kershaw and Lorrie Morgan

    The lead single and title track from Sammy Kershaw's sixth studio album, "Maybe Not Tonight" became a Top 20 hit for the pair in 1999. Kershaw and Morgan married in 2001 but divorced due to irreconcilable differences six years later.

  • "Maybe He'll Notice Her Now"

    Mindy McCready and Lonestar's Richie McDonald

    Released in 1996, "Maybe He'll Notice Her Now" became the third single from Mindy McCready's breakout debut record Ten Thousand Angels. Featuring Richie McDonald, the former lead singer of Lonestar, the aching ballad became a Top 20 hit for the pair.

  • "Hopelessly Yours"

    Lee Greenwood and Suzy Bogguss

    "Hopelessly Yours," written by Keith Whitley, Curly Putman and Don Cook, has been recorded by many major country artists, including George Jones and John ConleeLee Greenwood and Suzy Bogguss' version became a huge success for the pair in 1991, hitting No. 12 on the Billboard Hot Country chart. The collaboration also earned them a Grammy nomination for Best Country Vocal Collaboration the following year.

  • "I Fall to Pieces"

    Aaron Neville and Trisha Yearwood

    Aaron Neville and Trisha Yearwood put their own spin on this classic Patsy Cline tune for a special cross-genre duet album Rhythm, Country and Blues, which was released in 1994. The song found modest success on country radio and went on to snag the Grammy Award for Best Country Collaboration with Vocals in 1995.

  • "I'm So Happy I Can't Stop Crying"

    Toby Keith and Sting

    This unexpected duet became a surprise hit for Toby Keith and English rocker Sting. The song, which was originally released as a solo single by Sting a year earlier, was featured on Keith's fourth studio album Dream Walkin' in 1997. The song made it to No. 2 and gave Sting his first and only hit (so far) on the Billboard Hot Country charts.

  • "When You Say Nothing at All"

    Keith Whitley and Alison Krauss

    Alison Krauss recorded her own version of "When You Say Nothing at All" for the 1994 all-star project Keith Whitley: A Tribute Album. Not long after the cover began climbing up the country charts, a radio disc jockey decided to edit his own version of the song with Whitley's original to create a duet. This unofficial release was never made widely available, but DJs across the U.S. played the version regularly on their stations due to demand from listeners.

  • "Not Too Much to Ask"

    Mary Chapin Carpenter and Joe Diffie

    This emotional ballad from Mary Chapin Carpenter and Joe Diffie was selected as the second single from Carpenter's 1992 record Come On Come On. The two 90s country heavyweights took the song to No. 15 on the country charts and earned a nomination for Best Country Collaboration with Vocals at the 1993 Grammy Awards.

  • "This One's Gonna Hurt You (For a Long, Long Time)"

    Marty Stuart & Travis Tritt

    This 1992 hit collaboration was the lead single and title track of Stuart's sixth studio album. Written by Stuart, "This One's Gonna Hurt You (For a Long, Long Time)" made it to No. 7 on the Billboard Hot Country Songs chart and kept the pair's streak of hit duets rolling.

  • "Tell Me About It"

    Tanya Tucker and Delbert McClinton

    The third single from Tanya Tucker's 1992 record Can't Run from Yourself, "Tell Me About It" finds the country talent teaming up with blues rocker Delbert McClinton. The fan favorite peaked at No. 4 on the Billboard Hot Country Songs chart.

  • "I Will Always Love You"

    Dolly Parton and Vince Gill

    This version of Dolly Parton's classic hit "I Will Always Love You" was never meant to be a single. After the pair performed it together during an appearance at the Grand Ole Opry, DJs began airing a recording of the performance. The bootleg got so much airplay and attention that Parton decided to record a studio version with Gill for her 1995 album Something Special. The official single made it to No. 15 on the Billboard charts and earned the title of Vocal Event of the Year at 1995 CMA Awards.

  • "Somewhere in the Vicinity of the Heart"

    Shenandoah and Alison Krauss

    This special collaboration served as the lead single and title track from Shenandoah's six studio album. The band's collaboration with Krauss spent an impressive 20 weeks on the Billboard Hot Country Singles chart and peaked at No. 7. The critically acclaimed duet won a Grammy Award for Best Country Collaboration with Vocals and Vocal Event of the Year at the CMA Awards.

  • "By My Side"

    Lorrie Morgan and Jon Randall

    Lorrie Morgan and Jon Randall released their duet "By My Side" in 1996 and tied the knot that same year. The lead single from Morgan's fifth record Greater Need became a Top 20 success on the Billboard Hot Country chart. Ironically, Morgan originally wanted to record the duet with Sammy Kershaw, whom she would marry in 2001, two years after splitting with Randall.

  • "Honky Tonkin's What I Do Best"

    Marty Stuart and Travis Tritt

    The third Stuart and Tritt collab to make this list, "Honky Tonkin's What I Do Best" was the first single and title track from Stuart's ninth studio album. It peaked at No. 26 on the Billboard charts and became a Top 10 hit in Canada. The track snagged nominations for Vocal Event Of The Year Award at the 1996 CMA Awards and Best Country Collaboration with Vocals at the 1997 Grammy Awards.

  • "Still Holding On"

    Clint Black and Martina McBride

    Penned by Black, McBride and Matraca Berg, "Still Holding On" became a hit ballad for the country stars in 1997. The track became the lead singles from both Black's Nothin' but the Taillights record and McBride's LP Evolution. Their beautiful melding of voices earned "Still Holding On" a nomination for Best Country Collaboration with Vocals at the 1998 Grammy Awards.

  • "Burnin' the Roadhouse Down"

    Steve Wariner and Garth Brooks

    The title track and third single from Steve Wariner's 1998 record is a catchy, fun collaboration with Garth Brooks. The longtime friends and collaborators took the track to No. 26 on the Billboard Hot Country chart.

  • "Just to Hear You Say That You Love Me"

    Faith Hill and Tim McGraw

    Another powerhouse collaboration from Faith and Tim, "Just to Hear You Say That You Love Me" served as the second single from Hill's hit 1998 record Faith. This track was the couple's first duet since "It's Your Love" became a massive success, and it didn't disappoint. The song, which was written and originally recorded by Diane Warren, peaked at No. 3 on the Billboard Hot Country chart.

  • "What If I Said"

    Anita Cochran and Steve Wariner

    In 1997, Steve Wariner teamed up with emerging artist Anita Cochran for their aching, honest duet "What If I Said." The song became a huge hit, hitting No. 1 on the Billboard Hot Country charts and a nomination for Vocal Duet of the Year at the 1998 CMA Awards.

  • "Where Your Road Leads"

    Trisha Yearwood and Garth Brooks

    Another sweet collaboration from future husband-and-wife duo Trisha Yearwood and Garth Brooks, "Where Your Road Leads" was the title track of Yearwood's seventh studio album released in 1998. Penned by Victoria Shaw and Desmond Child, the duet peaked at No. 18 on the country charts.

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