10 Best Male Country Singers of the 2000s That Are Amazing

Here Are My Picks for the Best Male Country Singers of the 2000s!

In my humble opinion, some of the best male country singers of the 2000s were: Alan Jackson, George Strait, Keith Urban, Kenny Chesney and Tim McGraw.  But that’s just scratching the surface when it comes to talented artists from the 2000s era.  So without further ado, here are ten of our favorites that were amazing a couple decades ago and left a lasting legacy!

Best Male Country Singers of the 2000s

Let’s begin by talking about what made George Strait special.

George Strait

Not just in the 2000s but throughout history, George Strait is one of the most well-liked country music performers. His admirers, as well as the majority of the country music industry, affectionately refer to him as the “King of Country.” After growing up in Texas, Strait made his name famous by staying simple and kicking off the neo-traditional country movement.

Strait is undeniably one of the most successful country music singers, both male and female. He currently holds the record for having the most number-one singles of any artist across all charts. Besides his chart-topping, record-breaking success, he’s well-known for his incredible festival-style tours. Strait has a record number of awards; he’s been inducted into several halls of fame. He is currently beginning a tour with Chris Stapleton and other fantastic acts.

Favorite Song

It’s pretty obvious that Strait produces amazing songs, especially through the 2000s. Unfortunately, that makes it difficult to choose a favorite song. However, my favorite song by George Strait is I Cross My Heart. It’s a popular southern wedding song with lyrics that promise the world to each other. His voice is showcased extremely well and complements the melody. The song is truly a timeless classic.

Alan Jackson

Is Alan Jackson one of the top male country singers of the 2000s?

If there was every someone who was able to blend old with new, well, it would have to be Alan Jackson. Another member of the neo-traditional movement, Jackson is right behind George Strait in success. Born and raised in Georgia, it’s obvious that Jackson’s music is intended to remind you of your childhood and where you came from. 

Jackson puts a great deal of effort into his music, with many of his songs referencing his childhood or people in his life. His success is evident from the tremendous number of awards and honors. Jackson has been inducted into several halls of fame, including the Georgia Music Hall of Fame and the Country Music Hall of Fame. With plans to further his career, he is still touring and giving performances at the moment. 

Favorite Song

As previously mentioned, Jackson references his childhood and people from his personal life in his music. The song Drive is a great example of this. The song was written as a tribute to his father, Gene. It serves as a reminder to keep the good memories of your childhood close to your heart. 

Keith Urban

It’s not often that you see artists from other countries infiltrating the country music industry. However, Keith Urban did just that—and he did it well. His successful self-titled debut album featured the hits It’s a Love Thing and Your Everything

With constant chart-topping releases throughout the 2000s, Urban achieved the majority of his success. He’s made a name for himself in the industry with both his incredibly strong solos and his complementing abilities as a duo partner. Over the years, Urban has become one of the most successful international country music artists ever.

Favorite Song:

One of his best songs is Raining on Sunday, a romantic reminder to spend time with the one you love. The lyrics reference the fact that life can drag you down, things can get hectic. But remember to take that rainy Sunday afternoon and just stay in bed with your loved one. Slow down and be with them, because you never know what’s going to happen on Monday. 

Kenny Chesney

Is Kenny Chesney one of the greatest male country singers ever?

Kenny Chesney, a four time consecutive winner of Entertainer of the Year, was one of the most popular country artists during the 2000s. His songs often include references to the beach or summer, two-toned Chevys, and shift work. It’s pretty obvious he considers the beach a place to sit back and relax with a cold beer in his hand. 

Chesney is more of a symbol of country summer fun, with his constant references to being happy with what you have. He’s well-known for not only his music but also his ability to entertain at his shows. With a great many awards and honors, and several chart-topping hits, it’s safe to say Chesney has been both successful and popular.

Favorite Song

The best song that Chesney has come out with is definitely No Shoes, No Shirt, No Problem. It’s one of his most popular songs for a reason. The song’s lyrics are a gentle reminder to unwind and forget about the little things in life. Kick off your shoes and enjoy your toes in the sand.

Tim McGraw

Tim McGraw was undoubtedly one of the most significant musicians of that decade, even though his career didn’t start until before that year. He has steadily grown to be a significant figure in the country music business, with more than 25 songs that have reached the top of the charts and numerous amazing tours.

McGraw is not only a musical artist; he has also ventured into acting. With supporting roles in films like The Blind Side and Friday Night Lights, he’s been a genuine sensation in the entertainment industry. McGraw has a great many awards and nominations, and it seems as though he will continue his career for many years to come. He’s no doubt one of the top country male singers of the 2000s era.

Favorite Song

It’s Your Love is undoubtedly one of the most romantic, heartfelt songs of our time. The lyrics are beautiful, and the song is only made better when he duets with his wife, Faith Hill. It’s often played at the weddings of country music fans and is often the bride and groom’s first dance. There are not many songs that beat it.

Toby Keith

American country music singer Toby Keith is one of the most popular singers of his time. During the 2000s, he released a number of incredible albums, each including chart-topping songs. His most popular songs include the extremely patriotic Courtesy of the Red, White, & Blue and the somewhat humorous How Do You Like Me Now?

One thing you can say about Keith is that he is an extreme patriot. It’s also undeniable that he has quite the sense of humor. Keith has dabbled in the film industry in addition to the music business, lending his voice to soundtracks and even playing a supporting role. In an effort to recover and treat a number of physical ailments, Keith is currently taking a break from his career. 

Favorite Song

Among the long list of incredible songs that Toby Keith has released, Courtesy of the Red, White, & Blue is absolutely the best one. The song describes his feelings on attacks on the country and what he believes the country’s actions have been and should be. It’s a patriotic song about strength and the courage to fight back. 

Brad Paisley

Brad Paisley is definitely one of my all-time favorite artists. He gained popularity quickly in the early 2000s and his career just took off. Growing up in Glen Dale, West Virginia, he began writing music at an early age. The first song that he wrote at 13, Born on Christmas Day, was even featured on his album Brad Paisley Christmas.

Paisley is known for his amusing or romantic lyrics. He’s made a name for himself as both a solo artist and a duet partner. Inductions into the Grand Ole Opry and the Country Music Hall of Fame. Paisley continues to tour to this day.

Favorite Song

Both Whiskey Lullaby and Remind Me are at the top of the list when it comes to Paisley. Both songs sound amazing when he sings them solo. But as mentioned before, Paisley makes an incredible duet partner. So both the solo and duet versions of these songs are top tier. Both songs are about heartbreak and romance. What someone loses, whether it be over time or a tragic loss, when they lose their partner.

Blake Shelton

Blake Shelton broke into the country music industry with his debut single, Austin. It spent five weeks at number one on the Hot Country Songs Chart. From then on, Shelton topped the charts consistently. Songs like Ol’ Red and Some Beach brought Blake to fans’ attention.

While Shelton’s career began in the early 2000s, it has continued successfully for over two decades now. Many of his songs were influenced by his erratic love life. Several years into his career, Shelton was inducted into the Grand Ole Opry and the Oklahoma Hall of Fame. These are just a couple of his incredible achievements.

Favorite Song

God’s Country is definitely one of Blake Shelton’s best songs. It’s a song for many of us who grew up on a farm or were raised deep in the “holler.” To remind us where that land and success really comes from. While not everyone feels that way, a good many of his fans understand exactly what this song means.

Travis Tritt

After signing with Warner Bros. Records in 1989, Travis Tritt took the country music industry by storm. With certified platinum albums and even a triple-platinum album plus all of his chart-topping songs, you can’t deny Tritt’s ability to win over the fans. After growing up in Georgia, it’s obvious his childhood has influenced his music career.

Aside from his solo career, Tritt is known for some pretty spectacular collaborations. He’s even won two Grammy Awards for his duets with other incredible artists. While his career has slowed down since 2007, Tritt is still a fairly popular artist. He is currently still touring the country. 

Favorite Song

Among the long list of incredible songs by Travis Tritt, It’s A Great Day to Be Alive is undoubtedly the best song he’s released. Tritt has an exceptionally unique voice that works well in so many songs, this one included. The song serves as a reminder that no matter what you’re going through, there are things to be grateful for. Listening to it really brings you out of your head and back to that reality.

Rascal Flatts

Formed in 1999, Rascal Flatts is one of the most popular all male groups in the country music industry, today and in history. During the 2000s, the group recorded for Lyric Street Records, releasing six studio albums certified platinum or higher. Of their more than forty singles, the Rascal Flatts have had sixteen number one hits on the charts. 

Rascal Flatts is known for a number of their hits, especially songs like Me and My Gang and Melt. Their style ranges from emotional, tug-at-your-heartstrings songs to upbeat, pump-you-up melodies. They have received and continue to receive awards and nominations for their incredible works.

Favorite Song

Praying for Daylight is one of Rascal Flatts’ best hits, yet. While it is emotional lyrically, the melody still has an upbeat and positive vibe. The lyrics are exceptionally relatable, and of course the lead singer’s vocals complement the song to the max. 


While there were a number of artists whose careers were slowing down in the 2000s, there were also so many entering the country music industry. But the best male country singers of the 2000s included both old and new artists, both young and old. It was a time of change for country music, and all of these artists contributed in making country music what it is today.

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