Back in 2000, Chesney was headlining with Tim McGraw at the George Strait Country Music Festival in New York, when things got a little out of hand. Chesney jumped offstage and mounted a horse that belonged to a deputy who was patrolling at the show. The deputy was not amused and yelled at the star to dismount, but he refused. Some more police got (physically) involved and went to pull him off when Tim McGraw flew out of nowhere and grabbed one of the deputy’s throats.
If that doesn’t tell you how good of friends the two stars are, we don’t know what will! After all, it doesn’t seem like someone would risk getting arrested for assaulting a police officer for just anyone. Afterward, the department released a statement saying he knew the star wasn’t actually trying to “choke” the officer. But that wasn’t the only time the buddies sang together. In fact, they once staged an entire 20+ city tour together.
…And He’s Won a Lot of Awards
Kenny Chesney does not just make music; he makes good music. He makes the kind of music that brings tears to your eyes and has you feeling pretty much all of the feels. And these tear-jerkers have not only brought joy to millions of people for decades, but they’ve also won him an insane number of awards. The country superstar brought home the ACM award for Entertainer of the Year 5 times, including 3 years in a row from 2006-2008. He also won the same title at the Country Music Awards 4 times.
Unbelievably, the singer has yet to win his first Grammy, but he has been nominated a whopping 6 times, including in 2010 for Best Country Collaboration on “Down the Road.” In 2018, Chesney missed out on the CMA Awards due to a death in the family but was still nominated for Entertainer of the Year again, and he’s not going anywhere anytime soon!
His Net Worth is Through the Roof
Someone who’s consistently put out award-winning albums for over 2 decades probably isn’t going to be struggling financially, that’s for sure. Chesney is often seen lounging around in tropical paradises with a drink in his hand or hanging out on his boat, and that’s because when he’s not touring, he lives the (very) good life. Of course, you probably would too if you had a net worth of nearly $250 million. No wonder he goes on tour pretty much every year.
He makes over $40 million annually for doing so! But even though he’s got an outrageous net worth, he still remains humble and chooses not to spend too frivolously (at least, not as far as we can tell!) In fact, Rolling Stone magazine even commented that the singer “wears his fame very lightly.” And if you ask him what his happiest place on Earth is, he’d tell you it’s sitting in a small-town burger joint, biting into a juicy double that’s dripping with cheese.
He Was Gifted His First Guitar
So, you know how we said that Kenny was never exactly handed anything? Well, that’s not entirely true. The singer was gifted his very first guitar one Christmas during his teenage years. Although he had no idea how to play at the time, so he taught himself. He fell in love with the way it felt and knew that’s what he wanted to do for the rest of his life. Right then and there, he made the decision to pursue his musical passions and let go of the dream he had of playing professional sports.
He named the instrument “Terminor” and carried it everywhere with him. After he knew what he was doing, he started playing at different local venues. At first, he didn’t have his entire repertoire of songs, so he played covers at his gigs. He was able to make a name for himself locally before he hit the launchpad into superstardom.
Follow Your Heart
Even though it may seem like the Grammy-nominated multi-millionaire may be able to have pretty much any woman that he wants, he wasn’t always so gifted in that department. In fact, he’s no stranger to the heartache that comes along with being rejected by someone you love. During an appearance on Late Night with Seth Meyers, Chesney admitted that before he made it big, he poured his heart out into a song he wrote for this girl in Tennessee.
He recorded the song on a tape and gave it to the girl in class and went home, hoping that the next day she’d be all smiles and giggles. Unfortunately, she gave him the cold shoulder and pretty much avoided him from that point on. And all of this happened just a few years before he got his big break. She likely feels pretty foolish about ghosting one of the biggest superstars in country music, these days!