25 Country Songs You Won’t Believe Turn 25 in 2025

Twenty-five years ago, Alan Jackson and George Strait lamented the rise of pop-country, but a broader look at the top songs of 2000 reveal that they were absolutely …

Well, hold on. For better or worse, the two country legends kind of nailed it with „Murder on Music Row.“ Personal preferences aside, country radio has rarely sounded so progressive as songs from Faith Hill, Lonestar and Lee Ann Womack dominated. In some cases, country radio went all-in (see Womack’s mega crossover hit „I Hope You Dance“), while elsewhere, programmers kept an arm’s length.

„Can’t Fight the Moonlight“ by LeAnn Rimes is one example. This was a huge international hit that fell on deaf country ears. Hill’s „The Way You Love Me“ is another, although it cracked the Top 10.

In 2000, the Chicks won four CMA Awards, including Entertainer of the Year.

Shania Twain was country music’s big winner at the Grammys.

In the fall, Garth Brooks retired for the first time.

This list of country songs turning 25 years old in 2025 isn’t meant to make you feel old, although it’s hard to reconcile time after learning Billy Gilman’s career peak took place a quarter-century ago. Most of these songs can still be heard on great radio stations or stages today.

Others like Diamond Rio’s submission have found a home elsewhere. Country music was remarkably upbeat in the year 2000. We can’t claim this is a comprehensive list of songs turning 25 years old, but it does include the most popular hits, and from that group there’s only one heartbreak song.

That belongs to Travis Tritt, who hit No. 1 for the final time as the century turned over.

Click the titles of each song to listen to hits you forgot about, like „There Is No Arizona“ by Jamie O’Neal. Celebrate one-hit wonders and reminisce over a more cheerful time dotted with lyrics that were just a little cheesy.

25 Country Songs You Won’t Believe Turn 25 In 2025

Lee Ann Womack, „I Hope You Dance“

Lee Ann Womack’s quadruple-platinum certified ballad is one of the best songs of the 21st century. „I Hope You Dance“ is an inspirational message to a child, or a song of remembrance or even self-motivation during times of need.

The versatility of the lyrics helped make it a Grammy winner in addition to a CMA and ACM winner. Womack had hits before and after this song from 2000, but „I Hope You Dance“ will always be her signature.

Tim McGraw, „My Next Thirty Years“

It should be no surprise to see quite a few songs from Tim McGraw and his wife Faith Hill on this list. „My Next Thirty Years“ is a 30-year-old’s promise to live the rest of his life a little more simply than he has. The singer was actually 33 years old when it dropped in 2000, but who’s math-ing?

LeAnn Rimes, „Can’t Fight the Moonlight“

LeAnn Rimes‘ crossover hit was a huge international success, but it never really caught on at country radio. Diane Warren wrote „Can’t Fight the Moonlight,“ and it led the Coyote Ugly soundtrack in Summer 2000. Despite the lack of country radio airplay, it was still the No. 1 song on country sales charts that year.

The Chicks, „Goodbye Earl“

Quite a few songs on this list of country songs turning 25 in 2025 were available as album cuts before 2000 only to make their debut that year. That’s true for the Chicks‘ (then the Dixie Chicks) „Goodbye Earl,“ and a well-known music video starring Dennis Franz.

The lyrics of the song courted some controversy, and in fact, some radio stations refused to play it, while others provided domestic violence hotline numbers with every spin.

Keith Urban, „But for the Grace of God“

„But for the Grace of God“ doesn’t get too much airplay on contemporary radio stations in 2025, but it’s remarkable for being Keith Urban’s first No. 1 hit.

George Strait and Alan Jackson, „Murder On Music Row“

After performing „Murder on Music Row“ at the 1999 CMA Awards, George Strait included this Alan Jackson duet on his greatest hits album the next year. The two legends are found lamenting the rise of pop-country music, something traditionalists still seethe over today.

Despite never being an „official“ radio single, it earned the duo a pair of CMA Awards in 2000.

Faith Hill and Tim McGraw, „Let’s Make Love“

Tim McGraw and Faith Hill were the quintessential „it“ couple in 2000, so you can imagine how a steamy duet titled „Let’s Make Love“ was received. Twenty five years later it’s not considered to be their finest duet, but it certainly held the moment.

Toby Keith, „You Shouldn’t Kiss Me Like This“

Toby Keith’s „You Shouldn’t Kiss Me Like This“ was released to radio in 2000, but spent most of its chart life in 2001. The love song is a reminder of how versatile the late Country Music Hall of Famer was. Sonically it still holds up against ballads from contemporary artists.

Alan Jackson, „It Must Be Love“

This Alan Jackson song epitomizes a trend that the genre would do well to remember. Don Williams first drove „It Must Be Love“ up the charts in 1979, but Jackson was proud to make it his own 21 years later.

In 2025, it’s rare for an artist to do the same, and when it’s done, it’s kept as a deep cut.

Chad Brock, „Yes!“

Chad Brock wasn’t a one-hit wonder, but he came close. „Yes!“ was released to radio early in 2000, and it’d become his only No. 1 hit. It’s a plucky little love song that got stuck in your head and held a place in Gold catalogs for the better part of the decade.

If one wants to hear what 2000s sounded like in country radio, Brock’s song would be a good place to begin.

Sara Evans, „Born To Fly“

Sara Evans scored a huge No. 1 hit with „Born to Fly“ in 2000. The up-tempo inspirational was another great reminder to young people that it was important to dream big and expand horizons. We were big on motivation back then.

Jamie O’Neal, „There Is No Arizona“

Jamie O’Neal’s „There Is No Arizona“ was a beautiful accent to the pop-country that women of the early 2000s were producing. She was able to match them vocally, but this song — her first of two No. 1 hits — demanded you pay attention to her lyrics for a payoff. It’s an underrated gem, perhaps because O’Neal’s career sputtered after her first album.

Billy Gilman, „One Voice“

In 2000, Billy Gilman became the youngest male in history to score a Top 40 country hit. „One Voice“ — a song about violence — didn’t do great on country radio, but the historic moment made him a pop culture news story for most of the year. Songwriters Don Cook and David Mallory would earn a Grammy nomination for this song, but the singer would struggle to find a follow-up.

Diamond Rio, „One More Day“

Diamond Rio’s „One More Day“ quickly became the preferred song for funerals after it debuted in late 2000. It’s still a moving testimony, but 2001 was a particularly tragic year in American history, so this song was requested often.

Phil Vassar, „Just Another Day In Paradise“

Phil Vassar was an essential early 2000s country artist, and „Just Another Day In Paradise“ is the song that’s persevered above all others. The lyrics are just so relatable, then, now and forever

Faith Hill, „The Way You Love Me“

„The Way You Love Me“ was a No. 1 country song for Faith Hill that became a huge crossover hit. This song from her Breathe album helped make her a bonafide international superstar, and 25 years later, you’re still likely to hear it on the radio.

George Strait, „The Best Day“

„The Best Day“ isn’t often referred to as one of George Strait’s Top 10 songs, but that’s just because he has so many great songs that it won’t fit. The father-son ballad is a true gem that lives on 25 years after its early 2000s release. Like over five dozen Strait hits, it reached No. 1.

Lonestar, „What About Now“

„Amazed“ (from 1999) was still everywhere when Lonestar released „What About Now,“ an uptempo love song. It was among the most-played country songs of 2000, and if one were to make a Top 100 songs of the decade list, you’d probably find it.

Brad Paisley, „We Danced“

Before writing and releasing „I’m Gonna Miss Her“ in 2002, Brad Paisley was best-known for love ballads like „We Danced,“ a genuine country romancer from 2000. The singer tells the story of a relationship using a dance to pin down important moments. It’s a great song that foretold his songwriting talents.

Clay Walker, „Chain of Love“

It’s hard to find a song on this list of country songs turning 25 in 2025 that doesn’t exude positivity. Clay Walker’s „Chain of Love“ is no different.

The ballad is about paying it forward to your neighbors and how that chain may link back to you when its most needed. It’s the sort of great country song that puts a lump in your throat when you hear it.

Kenny Rogers, „Buy Me a Rose“

When „Buy Me a Rose“ hit No. 1 in 2000, it made Kenny Rogers the oldest country singer to top the charts, at age 61. He’s still the oldest primary artist to hit No. 1 — a few older artists have gone there as collaborators since.

The ballad finds the sweet spot of Rogers‘ voice, and he’s always been a tremendous teller of love stories. No, this song has not stood the test of time, but it’s still worth a spin or two.

Jessica Andrews, „Who I Am“

Jessica Andrews became a true one-hit wonder when in 2000, her song „Who I Am“ hit No. 1. She’d barely break the Top 20 afterward, something that’s not terribly uncommon when that first taste of success comes young (she was just a teen).

John Michael Montgomery, „The Little Girl“

John Michael Montgomery was as good of a country storyteller as you’ll find in the early 2000s. „The Little Girl“ is an inspiring story of faith and perseverance. The impact is just as strong today as it was 25 years ago.

Jo Dee Messina, „That’s the Way“

„That’s the Way“ was a No. 1 hit for Jo Dee Messina, but it’s hardly the song fans remember her for 25 years later. Late-’90s hits like „Bye Bye“ and „Heads Carolina (Tails California)“ define her career today, but there’s little doubt millions of fans were inspired by this chart-topper. In many ways it’s symbolic of what worked back then.

Travis Tritt, „Best of Intentions“

Country music is known for heartbreak songs, but this Travis Tritt ballad from 2000 is the only one of its kind on our (admittedly incomplete) list of songs turning 25 this year. „Best of Intentions“ was Tritt’s final No. 1 song.