25 Country Songs Turning 30 In 2025 [VIDEOS]

30 years have passed since the halfway point of one of the greatest decades of country music…the 1990s.

1995 was a huge year for country music. Garth Brooks, Alan Jackson, Travis Tritt, and Clint Black, affectionately known as the “Class of ’89,” were at the peak of their careers, Shania Twain released her first hit song, Kenny Chesney was fresh on the scene, Faith Hill’s career was on a meteoric rise, and the genre was introduced to the angelic voice of bluegrass great Alison Krauss.

The ’90s were arguably one of the best decades in country music history. While the Class of ’89 dominated the airwaves, women also had a massive presence on the radio. Female newcomers Shania Twain, Trisha Yearwood, Martina McBride, The Dixie Chicks, and Deana Carter were making their mark and paving the way for many of the artists topping charts today.

RELATED: BLAKE SHELTON, CLINT BLACK, & TRACE ADKINS PAY TRIBUTE TO ’90S COUNTRY DURING OPRY 100 CELEBRATION

We’ve compiled a list of songs released 30 years ago, smack dab in the middle of the Golden Decade of country music. The songs listed aren’t necessarily chart-toppers, but they will take you back in time and remind you why the ’90s are so fondly remembered.

1. “Sold (The Grundy County Auction Incident)” – John Michael Montgomery

“Sold (The Grundy County Auction Incident) was released in May of 1995 as the second single from John Michael Montgomery‘s self-titled debut album. It topped the country charts and was named the No. 1 single for the year by Billboard Hot Country Singles & Tracks.

The song was followed by the release of “I Can Love You Like That,” “No Man’s Land,” “Cowboy Love,” and “Long As I Live.” But “Sold” is arguably one of Montgomery’s most recognizable hits. The tongue-twisting, toe-tapping tune has been covered by Zach Top, Jake Hoot, Keith Urban, and Chris Jansen. 1995 ended with John Michael suffering a vocal chord injury that forced him to take a break.

2. “Haven’t Found It Yet” – Helen Darling

Helen Darling was one of the most underappreciated artists of the ’90s. This article’s author couldn’t make this list without including “Haven’t Found It Yet.” The song was released as the second single from Darling’s self-titled debut (and only) country music album.

Helen Darling was best known as a songwriter who had hits recorded by Pam Tillis, Reba McEntire, Mindy McCready, Little Big Town, and JoDee Messina. She sang background vocals for Garth Brooks’ 1994 song “The Red Strokes.”

3. “Check Yes Or No” – George Strait

“Check Yes Or No” was the lead single from George Strait’s Straight Out Of The Box album. Just like many of Strait’s previously released songs, it climbed to the top of the charts, earning George Single of the Year honors from both the CMA and ACM.

To date, “Check Yes Or No” is Strait’s most streamed song with nearly 300 million streams on Spotify alone and is one of King George’s most recognizable and beloved songs.

RELATED: MORE THAN 110,000 FANS SING ALONG WITH GEORGE STRAIT AT RECORD BREAKING CONCERT

4. “Bobbie Ann Mason” – Rick Trevino

Rick Trevino was arguably one of the most underrated artists of the ’90s. With hits like “She Can’t Say I Didn’t Cry” and “I Only Get This Way With You,” Trevino earned plenty of radio play. His single “Bobbie Ann Mason” became his third Top 10 hit.

5. “Bigger Than The Beatles” – Joe Diffie

There wouldn’t be ’90s country music without the iconic voice of Joe Diffie. 1995 found Diffie at the peak of his career with numerous chart-topping songs and award nominations to his credit. “Bigger Than The Beatles” was released in November of that year and became Diffie’s fifth and final No. 1 song. In 2024, Jon Pardi and Old Dominion covered the song for Hardy’s Hixtape: Vol. 3: Difftape.

6. “What Mattered Most” – Ty Herndon

1995 saw the arrival of Ty Herndon in the country music scene. In February, the velvety-voiced singer released his debut album and title track, What Mattered Most. The song rose to the top of the charts, earning Herndon his first No. 1 hit. 16 more singles were released in the years that followed, 2 more of which topped the chart. But, “What Mattered Most” is arguably Herndon’s most recognizable song and was a staple on every ’90s country playlist.

7. “Thinkin’ About You” – Trisha Yearwood

“Thinkin’ About You” was released four years after Trisha’s self-title debut album broke records and solidified her place in country music history as one of the genre’s most incredible female voices. By 1995, Yearwood had three platinum albums to her credit along with 8 Top 10 singles, a Grammy award, and too many award nominations to mention.

“Thinkin’ About You” was the second single released from the album of the same name and became her third No. 1 song.

8. “She’s Every Woman” – Garth Brooks

“She’s Every Woman” was one of Garth Brooks’ most anticipated song releases. It served as the lead single from his sixth studio album, Fresh Horses, a project fans had waited two years to hear. The album sold 3 million copies within six months, and “She’s Every Woman” peaked at No. 1 on the Billboard and Hot Country Songs charts.

Fans embraced “She’s Every Woman” as it was a change of pace from the singles that preceded it. Five of the six singles released from Brooks’ 1993 project, In Pieces, were up-tempo tunes. “Ain’t Goin’ Down (‘Til The Sun Comes Up),” “American Honky-Tonk Bar Association,” and “Callin’ Baton Rouge” were among them.

9. “I Like It, I Love It” – Tim McGraw

“I Like It, I Love It” was released as the lead single for Tim McGraw’s third studio album, All I Want. McGraw admitted that he didn’t love the song the first time he heard it. In fact, it wasn’t until he actually cut the track that he got excited about it.

“I didn’t think much about recording it,” he told WDRM-FM. “I was kind of cold on it, and I listened to it again, and for some reason, it hit me a whole lot different the second time around. And then when we went in and cut the track, the track just turned out so fun and so cool that it really didn’t matter how much I liked it anymore after we got to the track, because I loved it after that.”

It’s a good thing McGraw didn’t follow his initial hunch about the song because it went on to become one of his biggest and most recognizable hits.

10. “One Boy, One Girl” – Collin Raye

Collin Raye was one of the greatest voices of the 1990’s. His fourth studio album, I Think About You, produced six singles, including “One Boy, One Girl.”

The album became Raye’s fourth consecutive album to be certified platinum, making him one of only a few artists of the decade to achieve such a feat.

11. “Any Man of Mine” – Shania Twain

“Any Man of Mine” wasn’t Shania Twain’s first single released to radio, but it was the song that launched her career. “That’s the song I think that really, really broke me in a big way, because it was so different,” she said.

Considered edgy at the time, the song earned numerous award nominations, including two Grammy nods, and earned a two-week stay atop the Billboard Hot Country Singles & Tracks chart.

12. “Tall, Tall Trees” – Alan Jackson

Few people know that “Tall, Tall Trees” wasn’t an Alan Jackson original. The song was written by country legends George Jones and Roger Miller, and each released their own version in 1957 and 1970, respectively.

Alan Jackson recorded it as a single for his Greatest Hits Collection in 1995 after “stumbling across” Miller’s rendition. He recalled the story in the liner notes for his album, saying, “I’ve always been a big fan of Roger’s and when it came time to record a couple of new songs for this greatest hits, I couldn’t resist. After I recorded it, we found out that George Jones is a co-writer – I think George had even forgotten he’d written it. I’m proud to have the chance to record a song written by two of my favorites.”

Jackson took it to the top of the Billboard country charts to earn his 11th No. 1.

13. “I Don’t Believe In Goodbye” – Sawyer Brown

Sawyer Brown, with lead singer Mark Miller at the helm, was one of the hottest country groups of the ’80s and ’90s. “Some Girls Do,” “The Walk,” “The Race Is On,” and “Thank God For You” were radio staples prior to the release of “I Don’t Believe In Goodbye.”

More than a decade after they won Star Search and signed their first record deal, Sawyer Brown released “I Don’t Believe In Goodbye” as a part of their compilation Greatest Hits 1990-1995 album. The song became one of the last songs of the group’s to find radio success.

14. “Old Enough To Know Better” – Wade Hayes

Wade Hayes released “Old Enough To Know Better” as his debut single and title track to his first album. It was Hayes’ only No. 1 song, but die-hard ’90s country music lovers will agree that the soundtrack of the decade wouldn’t be complete without this toe-tapping hit.

15. “I’m Not Strong Enough To Say No” – Blackhawk

Blackhawk was one of the most underrated groups in country music history. Their unique style and sound set them apart from other groups of the decade, thanks to the recognizable vocals of lead singer Henry Paul. “I’m Not Strong Enough To Say No” was a single from their second studio album, Strong Enough.

16. “This Woman and This Man” – Clay Walker

Clay Walker was at the peak of his career in 1995. The year saw he release of his third studio album, Hypnotize the Moon, and the platinum certification of his previous album, If I Could Make A Living. “This Woman and This Man” was released in late 1994 and became one of the first charting successes of ’95. The song reached the top of the Billboard Hot Country Singles & Tracks chart and became Walker’s first multi-week No. 1 hit.

17. “Party Crowd” – David Lee Murphy

David Lee Murphy was one of the biggest stars of 1995 and earned a distinction no other artist on this list earned … the most-played country song of 1995. Murphy released his debut album, Out With A Bang, in early 1995. The project spawned three hit singles, including two that would define his career. His debut single, “Just Once,” was featured on the soundtrack for 8 Seconds, the iconic movie about rodeo star Lane Frost. The track was followed by “Party Crowd” and “Dust On The Bottle.” The latter would top the country charts and become Murphy’s signature song, but it was “Party Crowd” that became the most-played country song of the year.

18. “Keeper of the Stars” – Tracy Byrd

If you attended a wedding or a high school dance in the late ’90s, chances are high that Tracy Byrd’s “Keeper of the Stars” was on the playlist. Surprisingly, the song never reached the top of any chart, but was named ACM’s Song of the Year in 1996. It is one of Byrd’s most recognizable and played songs.

19. “Someone Else’s Star” – Bryan White

Bryan White was one of 1995’s biggest breakout stars with the release of his self-titled debut album. The project gave White his first No. 1 hits, “Someone Else’s Star” and “Rebecca Lynn,” and earned his debut album a Platinum certification for selling 1 million copies. The success of the album helped White secure two major awards the following year: Country Music Association’s Horizon Award and the Academy of Country Music’s Top New Male Vocalist award.

20. “Texas Tornado” – Tracy Lawrence

By the time Tracy Lawrence released “Texas Tornado” in April of 1995, he had already charted five No. 1 singles and had been named the Top New Male Vocalist of the Academy of Country Music. Lawrence released five studio albums and one live album during the decade and sent seven singles to No. 1 on the Billboard Hot Country Singles & Tracks chart, securing his place as one of the decade’s most successful artists.

21. “When You Say Nothing At All” – Alison Krauss

Unless you were a bluegrass aficionado, you had likely never heard of Alison Krauss until her cover of Keith Whitley’s “When You Say Nothing At All” hit the airwaves in 1995. The song was featured on Keith Whitley: A Tribute Album and on Krauss’s compilation album titled Now That I’ve Found You: A Collection. The release of “When You Say Nothing At All” launched Krauss and her band, Union Station, to country music prominence. Krauss was no stranger to success in the bluegrass world – she earned her first Grammy at 20 and was the winningest female artist in Grammy history until Beyonce surpassed her in 2021. But her newfound country music success took her by surprise.

“It’s a freak thing,” she said in 1995. “It’s kinda ticklin’ us all. We haven’t had anything really chart before. At all. Isn’t it funny though? We don’t know what’s goin’ on….The office said, ‘Hey, it’s charting,’ and we’re like, ‘Huh?'”

22. “And Still” – Reba McEntire

1995 marked the 20th anniversary of when Reba McEntire signed her first record deal. She had already racked up 19 No. 1 hits, 7 ACM Top Female Vocalist honors, 4 Female Vocalist of the Year trophies from the CMA, and had been named Entertainer of the Year for both the ACM and CMA. In May 1995, Reba released “And Still,” the final single from her 1994 album release, Read My Mind. The song peaked at No. 2 on the Billboard Hot Country Singles & Tracks chart, kept out of the top spot by Alan Jackson’s “I Don’t Even Know Your Name.” To date, “And Still” is one of Reba’s most beloved ballads.

23. “That Ain’t My Truck” – Rhett Akins

Rhett Akins is best known as an acclaimed country songwriter, but he had an impressive recording career in the mid-’90s. His songs “Don’t Get Me Started,” “She Said Yes,” and his breakout hit, “That Ain’t My Truck,” are considered ’90s country soundtrack staples. Akins’ son and future country star, Thomas Rhett, was only 5 years old when “That Ain’t My Truck” was released. The father and son have teamed up on occasion to perform the hit song during Thomas Rhett concerts, an event that delights fans every time.

24. “Darned If I Don’t (Danged If I Do)” – Shenandoah

It’s hard to believe that Shenandoah was only together for a decade before they disbanded in 1997. The band achieved more success in their 10-year career than many do in a lifetime. With hits like “Ghost In This House,” “Next To You, Next To Mine,” “Church On Cumberland Road,” “Sunday In The South,” and “Two Dozen Roses,” Shenandoah is easily one of the most legendary bands in country music history. In 1995, they released “Darned If I Don’t (Danged If I Do)” as the second single from their sixth studio album, In The Vicinity Of The Heart. It would become their last Top 10 hit.

25. “All I Need To Know” Kenny Chesney

31 years ago, country music fans were first introduced to Kenny Chesney. He released his debut album on the now-defunct Capricorn Records label, but failed to chart any of his singles. A year later, he released “All I Need To Know” on BNA. The title track reached the Top 10 and Chesney wouldn’t reach that milestone until late 1997 when he released “She’s Got It All” from his fourth studio album. But, “All I Need To Know” is arguably regarded as Chesney’s breakout hit and the touching ballad remains a fan favorite.