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Top 50 Country Songs from the 2000s

by Assessor

Whether you love spending an afternoon listening to the best country love songs of all time, the most patriotic country songs, or even funny country songs, country music always keeps us grounded in a changing world. The 2000s were no different, especially because it was a time of transition for America. From the Y2K scare (when we weren’t sure whether or not all computers would go haywire!) to the horrifying September 11 terrorist attacks to the devastation of Hurricane Katrina, no one who lived through this decade will ever forget it. It was a time when GPS was brand-new to consumers, the Internet was still a baby, when swine flu was our biggest health concern, and digital cameras were the latest new technology to own.

And country music kept us going through it all.

With favorites such as George Strait, Alan Jackson, and Faith Hill still at the forefront, the decade also ushered in a new group of performers, including Taylor Swift and Carrie Underwood. Sadly, we said goodbye during this decade to some of the all-time greats of country music including Johnny Cash and his bride, June Carter Cash, within months of each other. We also bid adieu to other legendary country music figures including Chet Atkins, Waylon Jennings, and Porter Wagoner. A new era had begun.

Here are a few of the top-of-the-chart hits to take you down memory lane to the decade no one can forget:


“How Do You Like Me Now?” Toby Keith

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“The Way You Love Me,” Faith Hill

“That’s the Way,” Jo Dee Messina

“The Best Day,” George Strait

“My Best Friend,” Tim McGraw


“It’s a Great Day to Be Alive,” Travis Tritt

“Don’t Happen Twice,” Kenny Chesney

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

“I’m Already There,” Lonestar

“One More Day,” Diamond Rio


“The Good Stuff,” Kenny Chesney

“Drive (For Daddy Gene),” Alan Jackson

“Living and Living Well,” George Strait

“Beautiful Mess,” Diamond Rio


“My Front Porch Looking In,” Lonestar

“Beer for My Horses,” Toby Keith and Willie Nelson

“It’s Five O’Clock Somewhere,” Alan Jackson and Jimmy Buffet

“Red Dirt Road,” Brooks & Dunn

“What Was I Thinking,” Dierks Bentley


“Live Like You Were Dying,” Tim McGraw

“Remember When,” Alan Jackson

“You’ll Think of Me,” Keith Urban

“When the Sun Goes Down,” Kenny Chesney

“American Soldier,” Toby Keith


“That’s What I Love about Sunday,” Craig Morgan

“As Good as I Once Was,” Toby Keith

“Bless the Broken Road,” Rascal Flatts

“Something More,” Sugarland

“Mississippi Girl,” Faith Hill


“If You’re Going through Hell,” Rodney Atkins

“The World,” Brad Paisley

“Summertime,” Kenny Chesney

“Jesus, Take the Wheel,” Carrie Underwood

“Leave the Pieces,” The Wreckers


“Watching You,” Rodney Atkins

“Never Wanted Nothing More,” Kenny Chesney

“These Are My People,” Rodney Atkins

“Take Me There,” Rascal Flatts

“Wasted,” Carrie Underwood


“Just Got Started Lovin’ You,” James Otto

“I Saw God Today,” George Strait

“Small Town Southern Man,” Alan Jackson

“Don’t Think I Don’t Think about It,” Darius Rucker

“Home,” Blake Shelton

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“I Run to You,” Lady Antebellum

“Whatever It Is,” Zac Brown Band

“It Won’t Be Like This for Long,” Darius Rucker

“River of Love,” George Strait

“Alright,” Darius Rucker


“Love Like Crazy,” Lee Brice

“The Man I Want to Be,” Chris Young

“All about Tonight,” Blake Shelton

“Come Back Song,” Darius Rucker

“White Horse,” Taylor Swift

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