The 10 Best Kenny Chesney Songs of All-Time

Kenny Chesney

Very few artists in either country music or any other genre have achieved quite so much success as Kenny Chesney. Over the past three decades, he’s sold over 30 million albums and scored over 40 Top 10 singles on the US Billboard Hot Country Songs and Country Airplay charts, 32 of which landed at the No.1 spot. He’s been awarded six Academy of Country Music Awards, nine awards from the Country Music Association, and become one of the biggest touring acts in the US. In tribute to one of country music’s most popular artists, here are the 10 best Kenny Chesney songs of all time.

10. Here And Now


According to Chesney, the central theme of his 19th studio album, Here and Now, is “how different people are around the world, yet how entirely similar they can be.” Apparently, one of their main similarities is a huge appreciation for the album’s titular track, an uplifting tune that, as notes, reminds us to spend less time worrying about the future and more time in the here and now.

9. Who You’d Be Today


Released in 2005, Who You’d Be Today tells the story of a person who died before their time and the grief and the sorrow of the one left behind, who can’t help but wonder who they’d be today if they were still alive. It ends with the narrator expressing hope that one day, they’ll see each other again. Heartbreakingly tender, and with a sentiment that many of us are only all too familiar with, it gave Chesney one of his biggest hits of the early 2000s, peaking at No.2 on the U.S. Billboard Hot Country Songs chart.

8. Living In Fast Forward


During interviews, Chesney has admitted that Living In Fast Forward was inspired by his rapid rise to fame. After toiling away for over a decade, his career suddenly went stellar in the early 2000s. “It’s been an amazing thing to live through and to see happen to you and to see your fan base grow to a point where it’s unbelievable to stand in front of that microphone every night and see how passionate they are about your music,” he’s said. “It’s everything I ever dreamed of and more.” Released in January 2006, it peaked at No.1 on the Billboard Hot Country Songs chart.

7. There Goes My Life


If there’s one thing that Chesney excels at more than almost anything else, it’s choosing ace songwriters to work with. There Goes My Life features the songwriting talents of Wendell Mobley and Neil Thrasher, who bring a sense of world-weary humanity to this tale of a teenage football player who gets blindsided when his girlfriend tells him she’s pregnant. In the end, the boy grows up, learns to appreciate fatherhood, and when his grown-up daughter leaves home, tells us “There goes my life, my future, my everything.” The song clearly struck a chord with fans, who kept it at No.1 on the Billboard Hot Country Songs chart for seven consecutive weeks in 2003.

6. Don’t Blink


As says, one of Kenny Chesney’s greatest talents is his ability to pull off huge, stadium-ready anthems as well as tender ballads like Don’t Blink. The story of a man celebrating his 102nd birthday, the song is a thought-provoking tribute to the idea of living life to the fullest. Released in 2007 as the second single from the album Just Who I Am: Poets & Pirates, it earned Chesney his thirteenth No.1.

5. Anything But Mine


If you thought Olivia Newton-John and John Travolta summed up everything there was to know about teenage summer romance in Summer Nights, wait till you hear Anything But Mine. Written from the perspective of a love-struck teenager who falls head over heels for a girl on vacation, it captures the ups and downs of summer romance perfectly. After debuting at No. 52 on the U.S. Billboard Hot Country Songs in January 2005, it eventually soared all the way to the No.1 position.

4. A Lot Of Things Different


A Lot of Things Different, which was written by Country Music Hall of Fame singer-songwriter Bill Anderson and songwriter Dean Dillon, was originally recorded by Anderson for his 2001 album of the same name. A year later, Chesney scored a major hit with it when he took this sobering account of a man who, nearing the end of his life, realizes he regrets more than he doesn’t to No.6 on the Billboard Hot Country Singles & Tracks chart.

3. The Good Stuff


By 2002, Chesney’s star was in the ascent. The Good Stuff, taken from the album No Shoes, No Shirt, No Problems, is proof of how it got there. A touching story about how easy it is to lose sight of what ‘the good stuff’ in life really is, the song took Chesney to the top of the US Billboard Hot Country Singles & Tracks chart for the fifth time, spending a total of seven weeks at No.1. It also proved one of his biggest crossover hits, peaking at No.22 on the Billboard Hot 100.

2. How Forever Feels


How Forever Feels could have turned out a very different song. According to Wikipedia, it was originally recorded by Tim McGraw, but when Taylor Swift’s first song subject, McGraw, decided not to release it, Chesney decided to make it his own instead. A lighthearted romp that leaves the big questions to one side for the day, it’s as bright and breezy as a summer day. Released in December 1998 as the first single from his 1999 album Everywhere We Go, it soared to No. 1 on the U.S. Billboard Hot Country Singles & Tracks chart. It also landed Chesney his first big pop success when it peaked at No. 27 on the U.S. Billboard Hot 100.

1. Somewhere With You


Chesney knows how to do fist-pumping stadium anthems, but he also knows how to craft a very fine love ballad like the deeply sensual Somewhere with You. Described by Chesney as “a tortured soul song,” it struck a major chord with fans when it was released in 2010, scoring Chesney a No.1 on the Billboard Hot Country Songs chart and becoming one of his first hits to cross over to the Adult Contemporary chart, where it peaked at No. 15.

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