Response to our just-released list of the best 25 country songs from the last 25 years was fast and fierce.
Several legendary artists failed to place a single song on the list, and fans noticed.
A strong case could be made for each of these artists, but remember, it’s a list of the 25 best “songs,” so you have to decide which individual recording should make this list.
That’s hard for most of the artists listed below, although we’ll concede that in once case, we may have just missed an obvious hit.
- Social impact, chart / sales data and awards they won helped shape the list, with staff and fan opinion breaking ties.
- There was no limit to the number of songs an artists could have on the list, although only one artist is featured twice.
- Four Country Music Hall of Fame artists and 11 ACM or CMA Entertainers of the Year made the cut.
Related: The Best 25 Rock Songs of the Last 25 Years
5 Artists Who Could’ve / Should’ve Been Included:
Luke Combs
Jason Kempin, Getty Images
1. Luke Combs: Luke Combs has 18 No. 1 hits on the Billboard Country Airplay chart. No artist has had as much success at country radio over the last decade, and he has the CMAs and ACMs to prove it.
While most of those awards are artist and album awards, he does have Single/Song of the Year wins for “Beautiful Crazy” and “Fast Car.” The latter — a cover of Tracy Chapman’s hit — is probably his best case to make this list. Their performance provided a great Grammys moment in 2024 and is likely to a radio staple for years to come.
Time could very well earn it a spot on a similar list in the future.
Keith Urban
Jason Davis, Getty Images
2. Keith Urban: A list of song awards won by Keith Urban underlines the struggle in choosing one from his catalog for this list. He won Grammys for “Sweet Thing” and “Til Summer Comes Around” and CMA Awards for “Blue Ain’t Your Color,” “We Were Us” and “Raise ‘Em Up.”
The ACM Awards rewarded “Days Go By” and “The Fighter,” and fans may say a song like “Stupid Boy” deserves dark horse consideration for the list.
He’s not the only 2000s country legend to be hurt by lack of consensus.
3. Kenny Chesney: “When the Sun Goes Down,” “Summertime,” “There Goes My Life” and “You and Tequila” are probably the four most obvious Kenny Chesney songs to include on a list of the 25 best country songs of the last 25 years. We’re happy to listen to a case for each.
Morgan Wallen
Mike Coppola, Getty Images
4. Morgan Wallen: Here is a fun question: What is Morgan Wallen‘s signature song?
The sheer size of his catalog of hits prevents any one song from standing out as a signature. Each one moves up sales, radio and streaming charts so quickly that you lose track. “They’re all good” isn’t helpful in this instance.
A strong argument could be made that social politics prevented him from winning Single/Song of the Year Awards or Grammys. We’re not here to re-write history, however. The songs that did win those awards are important songs, too, so until he drops one that flat-out makes your knees buckle, he may remain a Top 5 artist of the 2000s without a Top 5 Song of the 2000s.
George Strait
Matt Winkelmeyer, Getty Images
5: George Strait: George Strait‘s “Give It Away” won two ACM Awards, a CMA Award and a Grammy, so yeah, we might have missed there.
Which song has to go, though?
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