15 Best Country Songs From the ’90s We Play Over and Over

Country music in the 90s has a special place in music history and the hearts of many fans. The stars aligned for numerous artists who rose the charts and gained mainstream appeal.

Arguably a peak for the genre, the variety of music strands out from other decades. Likewise, the tremendous success of multiple songs rivals the pop, rock, and R&B music of the time. With unique voices, meaningful lyrics, and infectious melodies, 90s country songs feel distinctive, powerful, fun, and poignant.

Indeed, the biggest fans still play the greatest 90s country songs on repeat.

1. “Man! I Feel Like a Woman!”- Shania Twain (1997)

A girl power anthem of the highest degree, Shania Twain’s country/rock/pop hybrid gave a voice to women looking for a night on the town with their friends. The catchy and fun lyrics embolden everyone who listens to let their hair down and enjoy life.

“Man! I Feel Like a Woman!” peaked at number four on the U.S. Billboard Hot Country Singles & Tracks chart on June 12, 1999. It also peaked at number 23 on the Hot 100 chart, marking its widespread popularity.

With a clever music video that channels Robert Palmer’s “Addicted to Love,” the song continues to be a mainstay for karaoke and upbeat playlists, making it one of Twain’s most enduring hits of her career.

2. “Friends in Low Places”- Garth Brooks (1990)

In many ways, “Friends in Low Places” epitomizes not just 90s country music but country music in general. The song revolves around a man who shows up to an ex’s wedding uninvited, underdressed, and with a superior attitude that he’s better off with friends they’d deem inferior.

Brooks infuses the song with smug satisfaction that anyone who’s gone through a bad breakup can relate to. Listeners and radio play agreed with the song, spending four weeks at number one on the Hot Country chart. Fans still sing along to Country Music Association’s Single of the Year with glee to this day.

3. “Boot Scootin’ Boogie”- Brooks & Dunn (1991)

Country line dancing became a sensation in the 90s, and “Boot Scootin’ Boogie” got people on the floor more than any other song. With Brooks & Dunn’s unmistakable twang, this jam remains the perfect song for a country dance party.

At the same time, the catchy lyrics and melody make the tune one of country music’s most popular, whether you’re a dancer or not. The duo’s iconic song reached number one in 1992, and its popularity has not wavered.

4. “I Like It, I Love It”- Tim McGraw (1995)

One of Tim McGraw’s most memorable and crowd-pleasing songs, “I Like It, I Love It,” features an infectious beat and relatable lyrics for anyone falling in love. We all do the silliest things and change our priorities for that special someone. As McGraw sings, “Gotta wash my truck, dress up, pick her up to watch TV,” a million listeners sing along in agreement.

A seminal song for the artist, “I Like It, I Love It,” spent five weeks at the top of the Billboard Hot Country chart and even reached number 25 on the Hot 100 chart. It continues to be a favorite for fans everywhere.

5. “This Kiss”- Faith Hill (1998)

“This Kiss” marked the debut single from the album Faith, catapulting Hill to superstardom. The bright and happy love song epitomizes the rush of feelings the perfect kiss can give, from “unstoppable” emotions to a state of “perpetual bliss.”

The vibrant music video mirrors the song’s lively and romantic lyrics, with Hill donning various outfits among computer-generated flowers, butterflies, and rocket ships. “This Kiss” reached number one onBillboard’s Country Chart, seven on the Hot 100 list, and three on the Adult Contemporary Chart. It remains one of Hill’s trademark hits.

6. “Amazed”- Lonestar (1999)

Country music in the 1990s began a crossover appeal to pop and adult contemporary audiences that has continued to this day. Many songs contributed to this phenomenon, most especially Lonestar’s “Amazed.” The group’s most successful song, this ballad features romantic lyrics and rich vocals from lead singer Richie McDonald.

“Amazed” had an impressive run on multiple charts and award shows, marking significant milestones for the group and country music. The song’s crossover success led to spending eight weeks at number one on the Billboard Country Chart and reaching number one on the Hot 100 list, a feat few can boast about. It also won Song and Single of the Year at the Academy of Country Music Awards.

7. “How Do I Live”- Leann Rimes (1997)

This power ballad has one of the most fascinating histories in country music. At 14 years old, Rimes recorded the song for the film Con Air, but producers thought her age did not match the movie’s mature themes. So, they turned to Trisha Yearwood, who recorded her own version.

With both renditions released on the same day, each song achieved great success. However, Rimes arguably enjoyed the more significant and everlasting success. The song reached number two on the Billboard Hot 100 chart, and remained on the list for 69 weeks. It also held a spot in the top 25 best-selling country singles for a record 291 weeks from 1997 to 2003.

Rimes’s breathtaking and powerful vocals contribute to How Do I Live’s” beauty and enduring appeal. YouTube channels, such as this one, regularly react to the singer’s version with incredulous awe.

8. “Chattahoochee”- Alan Jackson (1992)

When released in 1992, “Chattahoochee” inspired feelings of summertime nostalgia. All these years later, the same winsome, fun-loving emotions the tune evokes still ring true. Named after the Georgia River, Jackson captures a genuine youthful spirit with lyrics about young love and days spent on the water.

It has become one of Jackson’s signature songs and a cornerstone for 90s country music. The song spent four weeks atop the Billboard Hot Country charts and won the CMA Song and Single of the Year awards.

“Chattahoochee” remains a classic thanks to the up-tempo beat, coming-of-age lyrics, distinctive guitar riffs, and Jackson’s easygoing vocals.

9. “Check Yes or No”- George Strait (1995)

One of the best-selling country artists in history, George Strait has dominated the charts with hit after hit. Numerous songs remain beloved as his music from the 90s has retained its appeal and charm. Still, “Check Yes or No” remains the sweetest and most timeless of his songs. It also showcases one of country music’s most steadfast characteristics: storytelling.

“Check Yes or No” tells a love story that follows a couple from their youth to adulthood, beginning with a simple note passed during school. She asks him, “Do you love me? Do you wanna be my friend?” with a check yes or no option. Don’t we all wish love could be this simple?

“Check Yes or No” became his 28th number-one hit on the Billboard chart and still ranks among the best of his record-breaking 60 number-one songs.

10. “Independence Day”- Martina McBride (1993)

Known as one of the most powerful vocalists in country music, Martina McBride also does something not all artists do. She consistently has released profound, socially conscious songs that deal with heavy subjects such as abuse and alcoholism. The first and still finest example, “Independence Day,” tells a heartbreaking story but one of great importance.

The accompanying music video, though difficult to watch, showcases the tragedy of a battered woman that far too many can relate to. The song’s success elevated McBride, but more importantly, it gave victims everywhere a voice and, hopefully, a chance to seek help.

11. “Strawberry Wine”- Deana Carter (1996)

Country music from the 1990s features multiple trademarks that make it still resonate with listeners today. The storytelling, nostalgic, and wistful feeling that many songs evoke reached their pinnacle with Deana Carter’s “Strawberry Wine.”

The song tells a coming-of-age tale between a teenage girl and a college boy working on her grandfather’s farm. Her recollection and fondness for a time as sweet as strawberry wine captures the nostalgic memories so many hold onto.

“Strawberry Wine” reached the number one spot on Billboard’s Country chart and remains Carter’s signature song.

12. “I Swear”- John Michael Montgomery (1994)

Although country fans think of John Michael Montgomery’s version of “I Swear” first, pop and R&B fans recollect the rendition by All-4-One. Though the group technically achieved more mainstream success with the song, dominating Billboard’s Hot 100 for 11 weeks, Montgomery released his first to significant success in the country genre. The song spent four weeks as the number-one song on the Hot Country list in 1994.

The ballad proves that exceptional music knows no bounds. Montgomery’s unmistakable, rich vocals give the song a unique sound, much different than All-4-One’s smoother version. In 2016, both artists collaborated on an updated rendition of the song, and to beautiful results.

13. “Fancy”- Reba McEntire (1990)

No one else sings like Reba McEntire. With one of the most recognizable voices in music history, she has conquered country music and the acting world. She enjoyed tremendous success in the 90s with numerous hits, but none quite have the iconic status as 1990’s “Fancy.”

Another song that epitomizes the dramatic storytelling that country music has become known for, “Fancy,” tells a tale of a daughter going to great extremes to escape poverty. Originally sung by Bobbie Gentry to great acclaim, McEntire’s version reached higher than the 1969 version, entering the top ten on the country charts. It still ranks among McEntire’s most iconic in her illustrious career.

14. “Should’ve Been a Cowboy”- Toby Keith (1993)

Toby Keith’s debut single launched his career and solidified him as one of the genre’s greatest. Though Keith enjoyed numerous hits throughout his career, many seminal for the artist and industry, his first number-one song holds a special place in the hearts of fans.

For one thing, “Should’ve Been A Cowboy” lets his vocals shine. Moreover, the spirited lyrics evoke a romanticism of cowboys that gives the song its endearing charm. Instantly recognizable, it’s one of the 90s’s most memorable and timeless tunes.

15. “I’m in a Hurry (And Don’t Know Why)”- Alabama (1992)

Simple but powerful, Alabama’s song “I’m in a Hurry (And Don’t Know Why)” features an unforgettable and evocative chorus that dominates the song. An exceptional chorus will get into listener’s heads almost immediately, and this Alabama hit proves to be one of the best.

Achieving massive success in the previous decade, “I’m in a Hurry (And Don’t Know Why)” marked Alabama’s 31st number-one song on Billboard’s Hot Country chart. Still, as far as their 90s hits go, this song reigns supreme as one of their catchiest and most beloved.