This 2004 fan favorite, and personal favorite, was the only song Kenny wrote 100% on his own. It’s still one of the most popular in his live shows. From his iconic, When The Sun Goes Down album, this hit never went #1 but came close spending several weeks at #2.  Chesney takes a look back at moments in his life that pop up when he hears a particular song. He even references songs from his youth, like “Jack and Diane,” “Only the Good Die Young,” and “Rock’n Me.”

The song is a mid-tempo in which the narrator recalls various moments in his life, and how he is reminded of each of them every time he hears a certain song. He references many of these songs, including “Jack & Diane“, “Only the Good Die Young“, and “Rock’n Me“. 

From Chesney’s Greatest Hits II, “I’m Alive” also featured guest vocals from Dave Matthews. Kenny wrote it with Dean Dillon and Mark Tamburino. It was first recorded by Willie Nelson for his Moment of Forever album, which Kenny also produced. It was recorded for Kenny’s 2008 album, Lucky Old Sun but wasn’t released until it was including in his Greatest Hits II. Kenny told Country Standard Time, he was inspired to write it following his divorce from actress Renée Zellweger: “Writing that song was a release. It was the best I’d felt in a long time after I wrote that song.”

According to the liner notes on Chesney’s The Road and the Radio album, he wrote this 2007 #1 hit while vacationing in Cabo San Lucas, Mexico. He was also there for a party to celebrate his friend, Sammy Hagar’s birthday.

Kenny co-wrote this 2013 top 14 hit with Keith Gattis. It was released as the 2nd single from his Life on a Rock album. He told CMT about the song, saying, “There is, and I think we all have that place. You had your group of friends, you fell in love at that place, you fell out of love at that place, you met a lot of really interesting people and, over time, you don’t realize that it’s becoming a really important spot in your life

Kenny co-wrote this 2009 #1 hit with Brett James. It was the only new track released from his Greatest Hits II compilation. It’s a song that recalls shenanigans of a couple of friends from the night before and recalling all the the people they met. After a few drinks and some mingling, he makes up stories of what he does and who he is, like “a doctor, a lawyer, a senator’s son / Brad Pitt’s brother, and a man on the run,”

Kenny Chesney and Skip Ewing wrote this classic. “You Had Me From Hello” served as the single from his 1999 album Everywhere We Go, and went on to become his 3rd #1 hit. Kenny was inspired to write it after seeing the movie  Jerry Maguire in 1996. In 1996. We all remember the famous line from the movie when Tom Cruise, who plays Jerry, tells Renee Zellweger, “You had me at hello.” That “hello” led to a marriage between Kenny and the actress in 2005. They divorced 4 months later.

Kenny Chesney wrote “Boston” with Mark Tamburino. According to Old Time Music, he was inspired to write the song from a personal experience. The city of Boston holds a special place in his heart, and it works in the song as the backdrop for a relationship. Boston has always been a special place for Chesney because of the love New England has for his music, and it’s where No Shoes Nation was born.

Chesney and Brett James penned this 2011 release. “Reality” was the 5th and final single from his project, Hemingway’s Whiskey. This #1 became his 21st in his career. He told Billboard, he got the idea for this one while sitting in a dentist’s chair, with a gas mask on. “There were a couple of years that I was so busy on the road I was kinda numb,”he said. “So, I’d go to the dentist to have something done and they’d put that gas mask on me and I’d be like, ‘Wow, that’s as relaxed as I’ve been in years!’ It was a great escape from reality for him. He went on to say, “I even asked my dentist, ‘I just want to come over here and sit some time, can you guys do that?’ He said, ‘We can’t do that, we’d get in trouble.’ I swear, I started writing that song on the way home.”

Written by Kenny Chesney, Neil Trasher and Wendall Mobley “Take Me There” was Rascal Flatts’ 8th #1 hit. It was the  lead-off single from their Still Feels Good album. Chesney told CMT, “I had the idea for that song several years ago, and I had written it down on a piece of paper in a notebook. I was going through a bunch of stuff and saw where I had written that down and had forgotten about it. The whole idea of the song was about meeting someone who still has their guard up from a previous relationship or whatever it is.”

“Turning Home” was a top 20 hit for David Nail, but it was written by Kenny Chesney and Scooter Carusoe. The single from 2010 was was Nail’s debut album, I’m About to Come Alive. The Kenny co-write went on to be a Grammy Award nominee. David Nail’s got a nod for Best Male Country Vocal Performance at the 53rd Grammy Awards.

“One Sip,” certainly sounds like it could have been a Jimmy Buffett song. But it was rocker Sammy Hagar and and his band The Wabos who recorded and released it in 2006. Hagar co-wrote the beachy vibe piece with Kenny Chesney. It was on his 14th solo album Livin’ It Up. It’s a toast to living your best life and celebrating moments.