The Top 5 Male Country Artists of the 2000s

In the 2000s, traditional and modern country music battled it out on the charts. It was the decade that Taylor Swift and Carrie Underwood debuted. We lost Chet Atkins, Waylon Jennings, and Johnny Cash, and Brooks and Dunn broke up. American Idol brought us Carrie Underwood, and Nashville Star brought us Miranda Lambert. But let’s look at the men. These male country singers had the most No. 1 country hits from the year 2000 to 2009. The list sticks to solo artists (or else Rascal Flatts would have reached the fourth spot).

5. Keith Urban

“But for the Grace of God” was the first song to hit the top spot for this guitar-slinging singer/songwriter from Australia. “You’ll Think of Me,” “Days Go By,” “Sweet Thing,” and “Only You Can Love Me This Way” also reached No. 1. Keith Urban released his first solo album in Australia in 1990. Two years later, he relocated to Nashville. In 1997, his band, The Ranch, was signed to Capitol Records and released one album with modest success. His self-titled American solo debut was released in 1999. It produced a couple of charting singles, and then the real success kicked in with the 2002 album Golden Road. 

4. Tim McGraw 

Curb Records released Tim McGraw’s first single in 1991, and the Nineties were a successful decade for the “Indian Outlaw” singer. As the calendar changed to 2000, however, McGraw started a run of 11 No. 1s during the decade. “My Next Thirty Years,” “Angry All the Time,” “The Cowboy in Me,” “Unbroken,” “Live Like You Were Dying,” and “Southern Voice” were just some of the big hits McGraw scored. McGraw had a successful decade as an actor as well. He appeared in supporting roles in The Blind Side and Friday Night Lights, and held down a lead role in Flicka.

3. Brad Paisley

Brad Paisley started his career in 1999 and went on to score 13 No. 1s in the 2000s. “We Danced,” I’m Gonna Miss Her (The Fishin’ Song),” “Mud on the Tires,” “The World,” “She’s Everything,” “Ticks,” and “Then” were amongst those 13 hits that topped the country chart for the Glen Dale, West Virginia, guitarist/singer. In 2003, Paisley co-wrote the book Jug Fishing for Greazy and Other Brad Paisley Fishing Stories.

[RELATED: 3 Songs You Didn’t Know Brad Paisley Wrote for Other Artists]

2. Kenny Chesney 

With over 60 Top 40 country singles, Kenny Chesney is also one of the most popular crossover country artists of all time. Over a third of those 60 reached the Top 40 of the Billboard Hot 100 pop chart. The Knoxville, Tennessee, native released his very first single in 1993, and first reached the top country spot in 1997. The 2000s, though, were Chesney’s most successful years. “Don’t Happen Twice,” “The Good Stuff,” “There Goes My Life,” “Anything but Mine,” “Summertime,” “Beer in Mexico,” “Don’t Blink,” and “Out Last Night” are a few of his 14 country No. 1s.  

1. Toby Keith 

Like Chesney, Toby Keith first released a single in 1993; but Keith’s debut, “Should’ve Been a Cowboy,” wasted no time and went straight to No. 1 on the country chart. Also like Chesney, Keith had his most successful years in the 2000s. “You Shouldn’t Kiss Me Like This,” “I’m Just Talkin’ About Tonight,” “ My List,” “Courtesy of the Red, White and Blue (The Angry American),” “Who’s Your Daddy,” “I Love This Bar,” “American Soldier,” Whiskey Girl,” and “American Ride” all hit the top country spot in the decade. In 2006, Keith starred in the movie Broken Bridges. He also wrote and starred with Willie Nelson in 2008’s Beer for My Horses. Toby Keith notched 15 No. 1 country singles between 2000 and 2009.

Photo by Kevin Mazur/Getty Images for NARAS