George Strait, Reba McEntire, Trisha Yearwood, and more head up our picks for our favorite ’90s country artists.
No era of country music comes close to matching the nineties.
No offense to Dolly, Loretta, Waylon, Johnny Cash, and Willie, but the genre was everywhere throughout the decade. From the first ever country-themed Super Bowl halftime show featuring Clint Black, Tanya Tucker, Travis Tritt, and The Judds in 1994 to Garth Brooks hosting Saturday Night Live and LeAnn Rimes performing for Pope John Paul II in 1999, country music was a part of every fabric of American life.
With hits like “Callin’ Baton Rouge,” “Two Pina Coladas,” and “Friends In Low Places” it’s easy to see why Garth Brooks became not only the poster boy for country music in the ’90s, but the top selling artist of the entire 20th century across all genres according to the Recording Industry Association of America. Like many Nashville stars, Brooks’ legacy will live on for years to come through his songs and on Music City’s Broadway strip with Friends In Low Places, his new bar set to open on November 29 with a live performance by Brooks that will be streamed on Amazon Prime.
Brooks & Dunn
The charisma and intimacy of Kix Brooks and Ronnie Dunn remain unparalleled in country music, even to this day. With a combined 45 awards, including a Country Music Association Award, ACM, and Grammy Awards, to their name, the iconic country duo’s vocal gymnastics was always it’s greatest asset, ranging from the high strung feel-good antics of “Boot Scootin’ Boogie” to the silky smooth and heartfelt “My Maria” and “Neon Moon.”
Deana Carter’s dynamite 1996 album Did I Shave My Legs For This? alone was enough to win her a spot on this list courtesy of songs like “We Danced Anyway,” “How Do I Get There,” and “Strawberry Wine.” The singer has remained in the country music spotlight thanks to award show collaborations and re-recordings, notably a 25th anniversary re-issue of the album in 2021 that included a version of the song featuring guest appearances from Vince Gill, Sara Evans, Martina McBride, Terri Clark, Lauren Alaina, and Ashley McBryde.
Photo: Courtesy deana.com
With over 30 million albums sold worldwide, Kenny Chesney has long become one of the most successful crossover country artists ever. This all stems from the foundation the Knoxville, Tennessee, born artist built in the ’90s on the back of successful hits like “How Forever Feels,” “She’s Got It All,” and “She Thinks My Tractor's Sexy,” the last of which remains one of his most popular songs to date.
Boisterous, blunt, and breathtaking trio The Chicks (formerly The Dixie Chicks) took the country world by surprise with 1998’s Wide Open Spaces and again the following year with Fly, making them one of the genre’s most impactful bands to close out the decade. Songs like “Wide Open Spaces,” cheeky murder ballad “Goodbye Earl,” and “Cowboy Take Me Away” combined Emily Strayer, Martie Maguire, and Natalie Maines’ knack for witty and sincere songwriting in a way that captivated listeners like few other artists could.
Billy Ray Cyrus
He may be known to many as Miley Cyrus’ father, but before her breakout on “Hannah Montana,” Billy Ray was one of the biggest new country music artists in the ’90s, bursting onto the scene in 1992 with his debut single “Achy Breaky Heart,” which became the first country single to be certified platinum since Kenny Rogers and Dolly Parton’s "Islands in the Stream" nearly a decade prior. Other charting hits like “Could’ve Been Me” and “Busy Man” further cemented his country behemoth status in the years to follow.
If The Chicks possess one of ’90s country’s most exhilarating women-led vocals, then Diamond Rio is one of the top men’s vocal groups of the time. Founded in the early ’80s as an attraction at Nashville’s Opryland USA, the collective wouldn’t release its debut single, “Meet In The Middle,” until 1991. The song was an instant success, making them the first band ever to debut at No. 1 on the Billboard Hot Country Songs charts. Other songs like “Love A Little Stronger” and “How Your Love Makes Me Feel” only continued the band’s legacy of polished vocals with a honky tonk backbeat.
With five No. 1 hits in the first half of 1995 alone, Joe Diffie is one of the most commercially successful country artists of the ’90s. Gone far too soon after dying from complications related to COVID-19 in March of 2020, Diffie is best known for songs like “John Deere Green,” “Home,” and “Prop Me Up Beside the Jukebox (If I Die).”
With three No. 1 hits on her first two albums, Faith Hill was not only one of the most successful country artists in the ’90s, but one of the most successful country artists of all time. Songs like the ballad “This Kiss,” “It Matters To Me,” and the empowering “Wild One” have all had a massive reach, touching new fans and helping to grow country music’s sphere of influence.
Songs like “Chattahoochee,” “Don’t Rock The Jukebox,” and “Gone Country” have sustained such popularity over the past three decades that they ought to be officially recognized as part of the Great American Songbook. Alan Jackson’s legacy to country music is one that can only be matched by the likes of George Strait and a handful of others, making his signature Georgia twang one of the most recognizable voices in country music.
Another of the ’90s most well-known new artists alongside Billy Ray Cyrus was Toby Keith, who’s debut single “Should’ve Been A Cowboy” reached No. 1. Keith didn’t slow down there though, having three more singles reach the same mark later on in the decade, including “How Do You Like Me Now?!” and “Who’s That Man”.
Following in the footsteps of fellow Eastern Kentuckians Loretta Lynn and The Judds, Patty Loveless brought a mix of mountain songs and coal town sounds together with a polished Nashville finish on tunes like “I Try To Think About Elvis,” “You Don’t Even Know Who I Am,” and “Hurt Me Bad (In a Real Good Way).” With five No. 1 hits, two Grammy Awards, and several other accolades to her name, Loveless was recently inducted into the Country Music Hall of Fame on October 22, 2023.
Cut from the same cloth as Shania Twain and Faith Hill, Martina McBride’s anthems about overcoming adversity like “Independence Day,” “A Broken Wing,” and “I Love You” became some of the decade’s biggest songs. This was largely due to the artist’s powerhouse voice, which has netted her the CMA Award for Female Vocalist of the Year award four times and the ACM's “Top Female Vocalist” award three times over her illustrious career.
Reba McEntire has risen from household name to cultural icon thanks to her multiple acting roles, philanthropy and role as a coach on NBC’s The Voice. However, hits like “Fancy,” a cover of “The Night The Lights Went Out In Georgia,” and Vince Gill duet “The Heart Won’t Lie” remain what her fans continue to lean on most, and rightfully so.
Photo: Courtesy opry.com
While his first album failed to receive mainstream success, Tim McGraw soon found it on the 1994 follow-up Not A Moment Too Soon featuring his first top 40 hit “Indian Outlaw.” From there, the charting songs and No. 1 albums flowed like a river, with 10 of his 16 albums having reached the top spot on Billboard’s Top Country Albums Chart, no doubt boosted by other highly successful songs like “Don’t Take the Girl,” “I Like It, I Love It,” and “My Next Thirty Years”.
Jo Dee Messina
With cuts like “Heads Carolina, Tails California,” “Stand Beside Me,” “I’m Alright,” and “Bye, Bye,” Jo Dee Messina’s first two albums — 1996’s self-titled project and 1998’s I’m Alright — provided one of the best one-two punches for debuts by a new artist in the entire decade. With the latter, the artist became the first female country artist with three multiple-week No. 1 songs from the same record. Messina carried this momentum into the next decade on 2000’s Burnand ensuing albums.
Although active since 1976, much of George Strait’s modern day success can be traced back to his albums, stadium tours, and other appearances throughout the 1990s. Some of the trailblazer’s most enduring songs like “A Love Without End, Amen,” “You Know Me Better Than That,” “Check Yes Or No,” and “Write This Down” came from the decade that also saw his acting debut as Wyatt “Dusty” Chandler in Pure Country and the launch of the George Strait Country Music Festival, which lasted from 1997 to 2001.
For years, fans have flocked to Travis Tritt for his easy-going, albeit straightforward songwriting, and for those who don’t, “Here's a Quarter (Call Someone Who Cares).” Other hits like “T-R-O-U-B-L-E,” “It’s A Great Day To Be Alive,” and “Help Me Hold On” also achieved major charting success in the ’90s.
Country music may not have had a better crossover into the pop space during the ’90s than Canadian superstar Shania Twain. Throughout the decade, the artist pushed boundaries and put female empowerment at the forefront of her music like nobody else at the time with hits like “Any Man Of Mine,” “Man! I Feel Like A Woman,” and “Honey, I’m Home,” among countless others. Her legacy is so impactful that many of today’s current country and pop stars, including Taylor Swift and Carrie Underwood, credit Twain as a major influence who helped pave the path for their future successes.
With seven albums released and five number one hits including “She’s In Love With The Boy,” “XXX’s and OOO’s (An American Girl),” and “Perfect Love” in the ’90s alone, Trisha Yearwood was a force to be reckoned with throughout the entire decade. Still a force on the stage to this day, Yearwood has gone on to have success hosting her own cooking show on Food Network in addition to releasing three cookbooks and hosting CMA’s Country Christmas in 2019.
Photo: Courtesy the Food Network
As we conclude our nostalgic journey through the most popular 90s country singers and bands, the hits still linger.. The artists from that time not only shaped the genre but also left an indelible mark on the very essence of American life. So, as the echoes of those timeless tunes fade into the horizon, we celebrate the enduring legacy of 90s country music.