Kenny Chesney's 10 Biggest Songs of All Time

#1 may surprise you
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By , Audacy

Kenny Chesney released his first album more than 25 years ago and has continued to create new music at a steady pace ever since.

The 52-year-old Tennessee native holds the record for most number one songs on the Billboard Country Chart, and he’ll have a chance to add to that number in the near future. Chesney is putting the finishing touches on yet another album as he continues to find new ways to make an impact.

“One of the hardest things about being this far into a career isn’t keeping up with what other people are doing, but telling your own truth in a way that’s not repeating yourself, that’s not just doing what you know works,” he said. “I know there are certain things I respond to: songs that rock you hard, lyrics that twist without being too clever, ballads that open up your soul and make you think.”

Chesney has 23 #1 country hits on his resume. Let's take a look back at the top 10 that have spent the most weeks on the chart.

10. WHEN THE SUN GOES DOWN

From 2004's When the Sun Goes Down, it edged "Perfect" by Sara Evans for the top spot on 4/3/04. "When the Sun Goes Down" spent a total of 22 weeks on the chart.

9. SUMMERTIME

From 2005's The Road and the Radio, it edged "Something's Gotta Give" by LeAnn Rimes for the top spot on 6/17/06. "Summertime" spent a total of 23 weeks on the chart.

6. REALITY

From 2010's Hemingway's Whiskey, it edged "Home" by Dierks Bentley for the top spot on 3/17/12. "Reality" spent a total of 24 weeks on the chart.

6. LIVING IN FAST FORWARD

From 2005's The Road and the Radio, it edged "Your Man" by Josh Turner for the top spot on 3/18/06. "Living in Fast Forward" spent a total of 24 weeks on the chart.

6. ANYTHING BUT MINE

From 2004's When the Sun Goes Down, it edged "That's What I Love About Sunday" by Craig Morgan for the top spot on 4/23/05. "Anything By Mine" spent a total of 24 weeks on the chart.

5. SETTING THE WORLD ON FIRE

From 2016's Cosmic Hallelujah, it edged "Blue Ain't Your Color" by Keith Urban for the top spot on 10/22/16. "Setting the World on Fire" spent a total of 26 weeks on the chart.

4. DON'T HAPPEN TWICE

From 2000's Greatest Hits, it edged "Grown Men Don't Cry" by Tim McGraw for the top spot on 6/9/01. "Don't Happen Twice" spent a total of 30 weeks on the chart.

3. THE GOOD STUFF

From 2002's No Shirt, No Shoes, No Problems, it edged "Courtesy of the Red, White and Blue" by Toby Keith for the top spot on 7/27/02. "The Good Stuff" spent a total of 31 weeks on the chart.

2. YOU HAD ME FROM HELLO

From 1999's Everywhere We Go, it edged "Something Like That" by Tim McGraw for the top spot on 9/18/99. "You Had Me From Hello" spent a total of 32 weeks on the chart.

1. HOW FOREVER FEELS

From 1999's Everywhere We Go, it edged "You Were Mine" by Dixie Chicks for the #1 spot on 3/27/99. "How Forever Feels" spent a total of 37 weeks on the chart.

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