Where Are They Now? 3 Successful Country Stars Who Dominated the 2000s

Country music is trending now, but for some, it was just as alive and well in the early 2000s as it is today. While artists have switched genres and bands have broken up, a few country stars continue to wow us with how far they’ve come. It may not be the early 2000s anymore, but listening to music from these artists will almost always take you back to that very different time.

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Rascal Flatts

Rascal Flatts took country music and music in general by storm when they released “Life Is A Highway” in 2006 on the Cars movie soundtrack. I don’t know about everybody else, but this song is simply one of my childhood staples. It’s hard not to think of “Life Is A Highway” and think of early 2000s music. From 2000 to 2009, the group also recorded six studio albums and garnered several No. 1 hits. They also won the Vocal Group of the Year award at the CMAs for five years in a row, from 2003 to 2008.

In February, Rascal Flatts just finished their 2026 Life is A Highway Tour, which Joe Don Rooney tells Music Row is a “high” they will be riding for “the rest of the year.”

Carrie Underwood

Underwood won her season of American Idol in 2005, just around the time when country music was shopping for a new blonde bombshell. She had a strong start, with her debut single “Inside Your Heaven” debuting at No. 1 on the Billboard Hot 100, making this the first time that any country artist had ever achieved that. Other hits like “Jesus Take The Wheel” and “Before He Cheats” also solidified her as country gold.

To this day, Underwood remains the highest-certified female artist in country music, a title the RIAA awarded her in October of last year. In a statement sharing the announcement, Underwood thanked the fans for over 20 years of support. “Accomplishments like this are more than I would have ever dared to dream of when I was starting out,” she admitted.

Underwood also took on a position as a judge for this year’s season of American Idol. How full circle is that?

Kenny Chesney

Although Kenny Chesney started recording music in the early 90s, the release of his 2002 album No Shoes, No Shirt, No Problem not only gave his growing fan base a name (No Shoes Nation) but also earned him top spots on the Billboard and Top Country Albums charts. In 2005, Chesney would be honored with the ACM’s Triple Crown Award, which included his first Entertainer of the Year win. Since 2004, Chesney has won this honor four times via both the ACM Awards and the CMAs.

How’s he doing now? Well, just this past year, Chesney was named Billboard’s No. 1 Country Artist of the 21st Century. In a statement, Chesney shared, “All I was ever trying to do was find the best possible songs, things that spoke to the heart of how No Shoes Nation lives.”

It seems like he outdid himself with that one.

Photo by: David Crotty/Patrick McMullan via Getty Images

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