17 Best 90s Male Country Singers

The 90s were the formative years of modern country music, a time when the genre still had deep ties to its early roots, but new stars mostly took over from the older Hall of Famers. Here’s a list of the best male country singers that carried us through the 90s.

1. Garth Brooks

Garth Brooks - Friends in Low Places

Garth Brooks is the number one artist in the history of country music genre and is one of the most successful music artists ever to grace a stage. A career rivaling the likes of Elvis Presley, Michael Jackson, and even The Beatles took off in the 90s with the success of songs like The Dance, Friends In Low Places, and If Tomorrow Never Comes. In 2000, he went into retirement for nearly a decade before returning with multiple album releases and world tours.

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2. Clint Black

Before Garth Brooks entered the scene, Clint Black was unquestionably the top male country artist. Despite being overtaken, he was still one of the best and biggest country stars of the 90s. An exceptional songwriter, he penned each of his tracks himself during the time, including Like The Rain, one of his biggest hits. Fans loved the newer sounds he brought to the genre that had more of a pop appeal than some of his contemporaries.

3. George Strait

George Strait - Check Yes Or No (Official Music Video)

George Strait was also very popular before the 90s, but he found the peak of his success during the decade. The 1990 release of his tenth studio album Livin’ It Up topped the country charts in album sales that year. In 1992, he starred in the movie Pure Country, performing the soundtrack for the film himself, which then went on to become the most successful album of his career.

With the record for the most number-one singles in any genre, the nickname King of Country is certainly a fitting title for him.

4. Tim McGraw

Tim McGraw - It's Your Love (Official Music Video)

Tim McGraw might have blended pop music into his country songs, but there’s no denying he’s a country artist at heart. He hit the scene hard in 1990 with the release of I Like It, I Love It but released multiple hit albums during the decade. Tracks like Don’t Take The Girl and Please Remember Me played on fans’ heartstrings while others like Indian Outlaw were more up-tempo. He’s also famous for forming a country music power couple with Faith Hill, another country star with whom he found success singing and writing songs.

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5. Alan Jackson

Alan Jackson - Little Bitty (Official Music Video)

It’s not hard to argue for Alan Jackson as the second-most successful country artist in the 90s behind Garth Brooks. A member of the Country Music Hall of Fame, he pioneered neotraditional country music that mixed classic country with honky-tonk music. His debut album may have come out in 1989, but the second single from the album reached number three on the country charts in 1990. Other songs he put out in the 90s like Chattahoochee, Don’t Rock The Jukebox, and Little Bitty topped charts and touched hearts around the country.

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6. Vince Gill


Vince Gill started his music career as a member of the country-rock group Pure Prairie League in the mid-70s. He broke out as a solo country artist in 1989, topping the 90s charts multiple times with songs like I Still Believe In You. Twenty-two Grammy Awards, 26 million album sales, and 50 Top 40 hits cemented his legacy as a country icon. He even joined The Eagles after the death of Glenn Frey and tours with the group sporadically to this day.

7. Trace Adkins

Trace Adkins - (This Ain't) No Thinkin' Thing (Official Music Video)

Trace Adkins will always have a special place in my heart. I grew up listening to my mother play his songs, and his debut single and album were released the same year I was born in 1996. His deep, rugged voice is oddly soothing and as country as can be. His debut album Dreamin’ Out Loud was followed by two more, cementing him as one of the biggest stars of that decade and one of the most influential artists of the late 90s. 

8. John Michael Montgomery

Sold (The Grundy County Auction Incident)

John Micheal Montgomery’s music runs the gamut of tempos and led to the star becoming a multi-platinum selling artist. He released six albums in the 90s, finding the most success with his debut album Life’s A Dance. The single I Love the Way You Love Me from that album found its way to the number-one spot on the country music charts and made it to number 60 on the Billboard Hot 100. His other popular releases include Sold (The Grundy County Auction Incident), Life’s A Dance, and I Can Love You Like That.

9. Toby Keith

Toby Keith - Should've Been A Cowboy (Official Music Video)

Toby Keith debuted in 1993 with his self-titled album. Tracks from it like Should’ve Been A Cowboy and A Little Less Talk And A Lot More Action launched him to number one and two respectively on the country charts and cemented his place as a star of country music in the 90s. The 1999 release of How Do You Like Me Now? became the top country song the following year and turned him into a multi-platinum artist for multiple decades. 

10. Billy Ray Cyrus

Billy Ray Cyrus - Achy Breaky Heart (Official Music Video)

While he may be better known now for being the father of Miley Cyrus, Billy Ray Cyrus had a more than serious music career. In 1990, he opened for Reba McEntire and released his first album in 1992, Some Gave All. It instantly launched him to number one on Billboard’s Top Country Albums, Billboard 200, and the top spot in multiple countries like Canada and Australia. Achy Breaky Heart may be the butt of jokes now, but it was an incredibly influential song that reached number one in the country and outside of the US—a feat that is incredibly rare. 

11. Travis Tritt

Travis Tritt - Here's a Quarter (Call Someone Who Cares) (from Live & Kickin')

Travis Tritt released six albums during the 90s, finding major success with the 1990 release of Country Club. His success garnered him two Grammy Awards during the decade and launched him from moderate popularity in the 80s to stardom in the 90s. Unlike some of the other artists of the time, his music features more of a soulful sound, incorporating gospel styles. That distinct sound and his writing all of his songs about his own life experiences helped separate him from the neotraditional movement of the time. 

12. Kenny Chesney

Kenny Chesney - She Thinks My Tractor's Sexy (Official Video)

Kenny Chesney is a country music star that’s found success throughout his career, but all of that started in the 90s. A successful but lackluster first two albums didn’t stop him from breaking through in 1996 and 1997 with Me And You and I Will Stand, both of which reached gold certification. The 1999 release of Everywhere We Go became his first platinum album and brought us classics like She Thinks My Tractor’s Sexy.

13. Brooks & Dunn

Brooks & Dunn - My Maria (Official Video)

Not to be confused with the illustrious Garth Brooks, the duo of Brooks & Dunn became some of the most influential country stars in the 90s. They put on spectacular shows, drawing huge crowds that could be enjoyed by fans that didn’t even particularly like country music. Their biggest hits of the decade included My Maria and Only In America, and it’s hard to find one of their songs that missed. Neon Moon was played in bars across the country and Boot Scootin’ Boogie contributed to the line-dance craze of the time.

14. Lee Greenwood

Admittedly, this one is on here because of personal bias. I grew up listening to Lee Greenwood’s songs during the 90s and heard his tracks on the radio all the time, so despite him being more popular in the 80s, he makes the list for me. His best-known song, God Bless The USA, was originally released in 1984 and was rereleased on the 1992 album America Patriot. Its popularity at American events made it one of the most-played tracks of the 90s and 2000s.

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15. Shenandoah

Shenandoah - Next To You, Next To Me (Official Music Video)

The country group Shenandoah has a rocky history of disbanding and reuniting, members leaving and being replaced, but that hasn’t stopped them from being widely popular. They started their journey in 1984 and have since produced 26 chart singles and one Grammy Award. Their most popular song releases include Two Dozen Roses (1989), Next To You, Next To Me (1990), and Somewhere In The Vicinity Of The Heart (1994).

16. Diamond Rio

Diamond Rio - Meet In The Middle (Official HD Video)

Diamond Rio rocketed to stardom in 1991 with the release of their hit track Meet In The Middle. It made them the first country group to have their debut single reach the top spot of Billboard’s Hot Country Songs chart and made sure the band found success throughout the 90s. While their debut album and single were immensely popular, their next releases weren’t as acclaimed. The 1996 IV album brought them back to the top, though they never reached the heights of their debut again. 

17. John Anderson

John Anderson is another country artist that found quite a lot of success before and during the 90s. His hit song Swingin’ in 1982 led to his breakthrough as a star, and after that, he never slowed down. The 1992 release of the Seminole Wind album secured his place as a country music icon. The title track of the album reached number two on the country charts, and Straight Tequila Night from the same album rose to the top spot. Throughout the 90s he continued to release charting albums and singles.

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