13 Of The Greatest And Most Famous Country Singers Of The 2000s

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Written by Laura Macmillan
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Country music has long been a favorite genre for many music lovers globally. And in the 2000s, there was no shortage of talented country singers.

If you had to pick one defining characteristic of country music in the 2000s, it would have to be its crossover appeal. Thanks to artists like Taylor Swift, Carrie Underwood, and Keith Urban, country music became more popular than ever with mainstream audiences.

This newfound popularity led to a surge in album sales and concert attendance and helped to make country music one of the most financially successful genres of the decade.

But who among these talented singers were the most notable ones? Here are thirteen of the greatest and most famous country singers of the 2000s.

1. George Strait

Born in 1952 in Poteet, Texas, George Strait is one of the most famous country music singers of the 2000s.

His musical career began in 1971 when he joined the army and performed in a country band called “Rambling Country.”

After his discharge from the army, Strait released his first album, Strait Country, in 1981. He then went from strength to strength with seventeen country #1 singles in the ’90s and nine in the 2000s with songs like “The Best Day” and “Give It Away,” and perhaps his most famous song of the 2000s, “She’ll Leave You With A Smile.”

He continued releasing music well into the next decade with his last album, Honky Tonk Time Machine, being released in 2019.

2. Taylor Swift

One of the most successful artists of all time, country crossover artist Taylor Swift was born in Reading, Pennsylvania, in 1989.

Swift’s career began in 2006 when she released her self-titled debut album. The album peaked at #5 on the Billboard 200 chart and sold more than 2.5 million copies in the United States. “Our Song” became Swift’s first #1 single on the Billboard Country chart.

In 2009, she released her second album, Fearless. The album topped the Billboard 200 chart and won four Grammy Awards, including Album of the Year.

She then went on to dominate the 2010s with some of the biggest songs of the decade.

3. Kenny Chesney

Next up we have Kenny Chesney, who was born in 1968 in Knoxville, Tennessee. The youngest of three children, Chesney was raised in a working-class family and showed a passion for music from an early age.

Chesney’s first album, In My Wildest Dreams, was released in 1994 and over the following years, he released a string of successful albums and singles, cementing his status as one of the most popular country singers of the 2000s.

Some of his most famous songs from this period include “She Thinks My Tractor’s Sexy,” “Don’t Blink,” and “Living in Fast Forward,” which have all done very well in the country music charts.

4. Brad Paisley

Another titan of the country music scene in the 2000s was Brad Paisley, who was born in 1972 in Glen Dale, West Virginia.

The young Paisley got exposed to country music at an early age, and he began playing the guitar when he was eight. After honing his skills for several years, Paisley made his professional debut in 1992, opening for country legend George Jones.

But it was the early 2000s that saw Paisley cement his status as one of country music’s biggest stars, thanks to many successful albums and singles, including “Mud On The Tires” and “Alcohol.”

In 2008, he was named Entertainer of the Year by the Academy of Country Music, solidifying his place as one of the biggest names in country music.

5. Toby Keith

Another artist that needs to be on this list is Toby Keith, who was born in 1961 in Oklahoma and spent his childhood on his family’s ranch.

His big break came in 1993 when he signed with Mercury Records and released his debut album, Toby Keith. The album’s lead single, “Should’ve Been A Cowboy,” became a massive hit, reaching the top of the country charts.

Keith would have several more hits throughout the 1990s and 2000s, including “As Good As I Once Was” and “I Love This Bar” and had fifteen country #1 singles over the first decade of the millennium.

He’s still very much active in the country scene with no signs of slowing down, releasing his most recent album Peso In My Pocket in 2021.

6. Tim McGraw

Born in 1967 in Delhi, Louisiana, Tim McGraw is another name synonymous with country music in the 2000s.

His childhood was shaped by his parent’s divorce, which left him feeling rootless. As a result, he turned to music as an outlet, and his talent soon became apparent.

After releasing his first album in 1993, the 2000s saw McGraw gain massive success with eleven #1 country hits, including “Live Like You Were Dying,” “Last Dollar (Fly Away),” and “Something Like That.”

His heartfelt songs resonated with fans worldwide, and he quickly became one of his generation’s most popular country singers.

7. Alison Krauss

Born in Decatur, Illinois, in 1971, singer and violinist Alison Krauss began playing the violin at age five and soon became a child prodigy, performing with bluegrass legend Lester Flatt when she was only ten.

In 1987, Krauss released her first solo album, followed by her major-label debut in 1989. Throughout the 1990s and 2000s, she continued to release highly acclaimed albums and toured extensively.

Her most famous song of the 2000s was probably her rendition of “Down To The River To Pray,” which was featured in the film O Brother, Where Art Thou?

Becoming a huge international hit, her performance helped popularize this old gospel song, which was first published in the Slave Songs of the United States in 1867.

8. Keith Urban

Born in 1967 in New Zealand, singer Keith Urban and his family moved to Australia when he was a child, and it was there that he developed a love for country music.

In the early 1990s, Urban formed a band called the Ranch, which released one album before breaking up. He then began a solo career, releasing his self-titled debut album in 1999.

The album’s first single, “But For The Grace of God,” became a hit in Australia and helped to launch Urban’s career in the United States. In the 2000s, he became one of the most successful country music singers, releasing a string of hit singles and albums.

His most famous song of the decade was “Somebody Like You,” which topped the country charts in 2002 and won him a Grammy Award.

9. Carrie Underwood

Born in 1983 in Muskogee, Oklahoma, Carrie Underwood rose to fame as the winner of the fourth season of American Idol in 2005.

After that, she went on to three studio albums in the 2000s, all of which have been certified Platinum or higher by the Recording Industry Association of America. She has also won numerous awards, including seven Grammy Awards and eight Academy of Country Music Awards.

“Jesus, Take The Wheel” is among Underwood’s most famous songs from the 2000s. The song succeeded commercially, reaching #1 on the Billboard Hot Country Songs chart. It also won a Grammy Award for Best Female Country Vocal Performance.

10. Rascal Flatts

Formed in 1999, Rascal Flatts is an American country music band. The group comprised lead singer Gary LeVox, bassist Jay DeMarcus, and guitarist Joe Don Rooney, who joined in 2000.

Rascal Flatts quickly rose to fame with their debut album, which featured the hit singles “Prayin’ For Daylight” and “I’m Movin’ On.”

The album was certified Platinum by the Recording Industry Association of America (RIAA) and helped to establish the band as one of the leading country music groups of the early 2000s.

In addition to their success on the album charts, Rascal Flatts also enjoyed a string of hit singles, including “These Days,” “Bless The Broken Road,” and “What Hurts The Most.”

Rascal Flatts has sold over 23 million albums and 55 million singles, making them one of the most successful country music acts of all time.

11. Alan Jackson

Next up we have country singer Alan Jackson, who was born in 1958 in Newnan, Georgia.

Released in response to the September 11 attacks, his most famous song of the 2000s was “Where Were You (When The World Stopped Turning),” which was released in 2001. It even won a Grammy the following year for Best Country Song.

Jackson is also known for hits such as “It’s Five O’Clock Somewhere,” “Remember When,” and “Good Time.”

12. Brooks And Dunn

Few country music singers have achieved the level of success enjoyed by Brooks and Dunn. The duo, composed of Kix Brooks and Ronnie Dunn, was formed in 1990 and quickly rose to prominence, thanks to their unique brand of country-pop.

While Brooks and Dunn enjoyed great success throughout the 1990s and 2000s, their most famous song of the decade was undoubtedly “Ain’t Nothing ‘Bout You,” which they released in 2001.

The catchy tune topped the country charts for five weeks and helped to cement the duo’s reputation as one of the hottest acts in country music.

13. Richie McDonald

And finally, we have singer Richie McDonald who is known for being the lead singer of Lonestar, a country music group formed in 1992 in Nashville, Tennessee.

Lonestar has sold over ten million albums worldwide, and they continue to be one of the most popular country music groups today.

The group achieved mainstream success in the late 1990s and early 2000s with their singles “Amazed,” “What About Now,” and probably their most famous tune of the decade “I’m Already There.” The song reached #1 on the Billboard Hot Country Songs chart and won a Grammy Award for Best Country Song.

Summing Up Our List Of Famous 2000s Country Singers

As you can see from the list above, the 2000s was a decade that saw the rise of many successful country music artists. These artists achieved great success in commercial popularity and critical acclaim.

Artists such as Urban, Underwood, Jackson, Brooks, and Dunn helped shape country music’s sound during this decade and are some of the most popular country music acts today.

But this list barely scratches the surface of amazing singers from the decade. Who do you think we missed? Let us know and we’ll update the post.

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Laura has over 12 years experience teaching both classical and jazz saxophone and clarinet. She now resides in California where she works as a session and live performer.