Eric Church debuted 20 years ago, but he’s hardly the only country music superstar to break that year. The year 2006 also introduced us to Kellie Pickler, Taylor Swift and Jake Owen.
Signature songs from George Strait, Carrie Underwood and Rascal Flatts all celebrate a milestone this year as well. Look at this list of 20 songs turning 20 in 2026 and ask yourself if this was among the best years ever in country music.
- In 2006, Kenny Chesney was the CMA Entertainer of the Year and “Believe” by Brooks & Dunn was Song/Single of the Year.
- Rodney Atkins‘ “If You’re Going Through Hell” was the most played song on the radio.
- George Strait was inducted into the Country Music Hall of Fame.
Read More: See the Most Played Country Song from the Year You Were Born
New artists included Sugarland, Jason Aldean and Dierks Bentley. All three — along with many others — went on to have massive careers in country music. In fact, by our count, there are eight future Hall of Famers represented below, in addition to the two who have already been inducted.
Each of these songs will evoke a memory, hopefully for the better. The love songs may stir feelings for the one who got away, while the rockers may take you back to a time when being wild and free was in style. It’s difficult to say these songs describe a specific era of country music.
Bro country was still years away, and programmers embraced sonic diversity. It was a great time to be a country music fan.
Enjoy this list of 20 songs turning 20 in 2026, and click on any of the song titles to hear them all over again.
20 Songs You Won’t Believe Turn 20 In 2026
Gallery Credit: Billy Dukes
The 25 Best Country Songs of the Last 25 Years (2000-2024)
The best country songs of the last 25 years were felt and heard. Commercial impact was a factor, but emotional impact is what separates these songs from others released in the 2000s.
Technically the century began in 2001, but we reached back to 2000 to summarize this list of top songs. Alan Jackson is the only artist with two songs, but you’ll find 11 Entertainer of the Year winners scattered across a playlist the required several stunning exclusions.
Curious as to why your favorite song missed the cut? Well, there are only 25 spots for the best of 25,000 country song releases. Hard decisions needed to be made!
Gallery Credit: Billy Dukes
