The year was 1999—a time of Y2K anxiety, denim everything, and an unforgettable chapter in country music history. As we turn the calendar to 2024, it’s hard to believe that some of the most iconic country songs are now hitting the quarter-century mark. These tracks not only climbed the charts but also became the soundtracks of countless lives, reflecting the heartache, joy, and stories that make country music timeless.

From soulful ballads to boot-stomping anthems, these songs are more than just hits—they’re milestones that remind us how much the genre has grown and evolved. These tunes still resonate today, bridging generations of fans. Let’s take a nostalgic journey through the country songs turning 25 this year and celebrate the music that shaped a decade.

 

1.  “I Hope You Dance” by Lee Ann Womack

 

 

2.  “Born to Fly” by Sara Evans

 

 

3.  “It Must Be Love” by Alan Jackson

 

 

4.  “You Shouldn’t Kiss Me Like This” by Toby Keith

 

 

5.  “Best of Intentions” by Travis Tritt

 

 

6.  “Go On” by George Strait

 

 

7.  “Goodbye Earl” by the Dixie Chicks

 

 

8.  “The Little Girl” by John Michael Montgomery

 

 

9.  “That’s the Way” by Jo Dee Messina

 

 

10.  “Don’t Happen Twice” by Kenny Chesney

 

(And in case you were wondering what songs turned 50 this year . . . “Rhinestone Cowboy” by Glenn Campbell, and “Feelins'” by Conway Twitty and Loretta Lynn were both released in 1975.)