He Dates Beauty Queens

Or at least, he did date a beauty queen at one point. In 2008, the musician went public about his relationship with 24-year old Amy Colley. The younger woman was a nurse at the time they met, but she was also Miss Tennessee back in 2005. One source who was close to Chesney reported to Star Magazine that when the two were together, Chesney was head over heels for her.

Things actually got so serious between them that he even met the former beauty queen’s parents, when he took a trip home with her for Thanksgiving and he brought her home to meet his family as well. But that wasn’t the only trip they’d take together. They were later seen together in several exotic destinations, cuddling and kissing on the beach.

But He Also Allegedly Cheats on Beauty Queens

Just as Kenny got together with Amy when things started to get rocky with a former relationship, so the cycle continued. Of course, Amy thought they were still an item when the country star was seen in Cancun with another woman, but she was in for some heartache when she heard her former beau was vacationing with someone else. It wasn’t just any other woman, though. It was Jenn Brown, the very first female Inside the NFL correspondent from ESPN.

One witness reported that the two obviously looked like they were touching each other constantly and “definitely looked like more than friends.” A heartbroken Colley had had enough at that point, and the two ultimately ended things. As far as the other girl, nothing ever got too serious with Brown.

Living La Vida Bachelor

Country artists tend to sing about love a lot and Chesney’s songs about having loved and lost and loved and lost again, and again…they’re all pretty much right on the money. Chesney has been in his fair share of relationships over the years. But relationships aside, he’s actually copped up to having slept with over 100 different women.

The star told Playboy that he prefers to live that way and that if he had to be stuck in a “regular” relationship with a wife and kids that he would very likely “blow his brains out.” But that doesn’t mean he never gave it a try at one point in his life…

Got Between 50 and Kanye’s Beef

Kanye West and 50 Cent have a little friendly competition going on that’s lasted for, oh, pretty much as long as they’ve both been in the music business. The beef stems from them fighting for the title of the King of Hip Hop. 50 was making his traditional rap and Kanye West came in with a mix of hip hop with a more pop vibe and his albums flew off the shelf. So, the rappers decided to have a little contest back in 2007. 50 dropped his album, Curtis, on the same day that Kanye released his album, Graduation. 50 Cent told everyone that if Kanye sold more CD’s than he did, he’d retire from the game altogether.

Just when the feud couldn’t get any more interesting, Chesney popped up in the middle of it and released an album of his own that day. But since he was a little late to the party, he wound up in third place behind Curtis in 2nd and Kanye with the gold.

Got in a Brawl with Police (and Tim McGraw)

Yep, you read that right. People can say many things about Kenny Chesney and his life but they can’t say he’s boring, that’s for sure! Fans got more than they bargained for when they went to see Chesney and McGraw perform at the George Strait County Music Festival in New York, back in 2003. After they had delivered the opening performances for the show, Chesney jumped on top of a horse – one that happened to belong to one of the deputies working at the concert.

The deputy shouted for him to freeze as he started to ride away. But before he could make it very far, another deputy came out and physically started to remove him from the horse when Tim McGraw jumped in and saved the day! Man, that would have been well worth the ticket price of that concert to see all of that go down.

Jumped the Gun

In 2016 at one of his concerts in Philly, Chesney had a blooper moment that revealed some sad (and false) information. The country music star announced to a crowd of about 70,000 people that Officer Christopher Dorman had passed away. The Delaware County police officer was shot 7 times by a drug dealer in the line of duty, including a shot to his face. He was scheduled to attend the Chesney concert but obviously couldn’t make it due to the fact he was in the hospital recovering.

But instead of making that announcement, the singer told his fans he had died. After the Delaware County Police Department saw what had happened, they took to social media to correct him and he ended up calling the officer after the concert to make his amends. He also invited him out for some beers when he was up for it.

He Performed at the White House

Performing at the White House is sort of a rite of passage for megastars. After all, not just anyone gets invited to entertain the President of the United States. The invite came from George Bush Jr. in 2006, when John Howard, the Australian Prime Minister, was set to come for a visit. Bush really wanted to impress him, so he set up a private concert with the country star in the East Room. As if performing for such an elite crowd wasn’t cool enough, when he got done singing, Bush gifted him with a custom-made pair of eel skin boots made by Rocky-Carroll.

Of course, it wasn’t just any custom pair. The details on the boots were commemorative of the evening and featured both the U.S and Australian flag. Two years later, Chesney came back to the W.H to perform the National Anthem for a special tee-ball game.

He Performed Live with Reese Witherspoon

It makes sense that everyone would want to see Reese on stage with Kenny Chesney. After all, she’s pretty much the perfect Southern belle. The actress attended a charity auction in her home state of Louisiana, thrown at the House of Blues by none other than Matthew McConaughey. During the event, one high roller threw down nearly $30,000 for a once in a lifetime chance to see Witherspoon jump on stage and sing along with the country star.

The performance was a huge hit with the crowd, who didn’t seem to mind that she didn’t exactly remember every lyric to the jam! The auction was created to support McConaughey’s non-profit organization dubbed: Just Keep Livin. The two stars performed their rendition of Johnny Cash’s hit song Jackson.

He’s Got a Huge Team Behind Him

It’s not unusual for celebrities to have entire entourages to support them through their hectic lives, and Chesney’s no different. But when you hear the word “entourage” you probably imagine a team of around 20 or so people. In Kenny’s case, it’s more like 120 people. The singer spends nearly all of his time on tour and is constantly on the move, having somewhere to be and something to do. So, he’s got a team member for pretty much everything. But don’t feel bad for his employees, because Chesney treats them with the utmost appreciation.

After each and every tour, he takes the whole team on a getaway for a week so everyone can relax. He also gives one lucky team member the profit from merchandise sales, which he chooses with a special lottery he made just for the occasion.

He Keeps a Strict Diet (Sometimes)

It may seem like celebrities always get to do pretty much whatever they want, whenever they want – but that’s actually far from the case. When on tour, Chesney’s manager wants him to keep to a balanced and healthy diet. It isn’t like he’s got a ton of time to eat, but one of his team members happens to be a personal chef that cooks him up heart and weight friendly meals like grilled chicken with veggies.

He’s still got access to a chef when he’s not touring, but that doesn’t mean he adheres to the same diet. Chesney says that he does try and eat somewhat healthy, but he also loves to eat. The star told CMT that he uses Sundays as a cheat day and eats anything he craves! The singer said, “If I wanted a chocolate-covered double cheeseburger, I’d eat it!”

He Cares About His Fans

While some performers could care less about their fans and are only in it for the money, Chesney is not one of them. He doesn’t care if you’ve bought a VIP, backstage ticket to his show or you’re in the back row – he cares about your experience. During each one of his venue changes, he makes sure to climb all the way up into the “nosebleed” section and check the sound quality, to ensure fans in the back still get a great show.

In 2015, two of his fans sat a few rows away from each other up in the nosebleeds and caught each other’s attention. They ended up exchanging phone numbers and getting married 3 years later! When Chesney found out, he invited them back for a VIP show. Awwww!

He’s Alive by a Twist of Fate

On September 11th, 2001, Kenny Chesney was scheduled to shoot a music video for his song “Tin Man,” in New York City – just a block away from the World Trade Center. But just days before they were bound to take off, complications caused them to postpone the shoot. That morning, tragedy struck when two planes were hijacked and crashed into the buildings of the WTC. Nearly 3,000 people lost their lives, and had Chesney been in ground zero, he very well could have, too.

Chesney says he was in the middle of Virginia on his tour bus when he saw the news after the attacks that morning. He attributes his not being there to his “guardian angels” and said that he feels incredibly lucky to be alive.

The Green…Box?

You often hear about celebrities hanging out in their green rooms before a performance. You probably imagine them sipping on champagne and eating 5-star meals in a fluffy robe, while someone rubs their feet as they warm up their vocal cords. Well, that may be the case in some situations, it definitely wasn’t when Anderson Cooper came to see Chesney in his “green room.”

At this particular show, Cooper met Chesney in a compartment that was so small, it was basically a box, large enough to seat 2 people, max. So, Cooper sat face to face with the star for a short interview, before the box was wheeled to the stage for his grand entrance. We know that Kenny Chesney is humble and everything, but man, can’t the guy at least relax on a proper couch before he performs?

Dreams of Playing Pro Ball

Kenny Chesney may be one of the biggest stars in country music history but that wasn’t always the direction he’d seen his life going. He always loved baseball, and when he was growing up he used to tell people that he wanted to play pro for a major team like the Boston Red Sox. His fate had other plans but luckily for him, though, he still gets to perform at the big games and meet his favorite players.

Despite being grateful for his successful music career, he still wanted to give baseball a try –  so he had decided to get out on the field and play some ball, so he reached out to Roy Halladay, the late pitcher for the Phillies. He told him that he wanted to play a “simulated” game with him and that he’d love it if Halladay would come at him with all of his might like it was the World Series. Surprisingly, 4 years later, Halladay was killed in a plane crash in the Gulf of Mexico. Chesney took to Twitter to post a photo along with the caption, “I lost a great friend today.”

He Upset the ‘Beyhive’

The “Beyhive,” or Beyonce’s superfans, get rather unpleasant (to say the least) when they feel that someone’s disrespected their idol. So, when Chesney got caught giving Beyoncé the apparent stink-eye during a performance she gave with the Dixie Chicks, her fans took to social media to express their outrage.

Things got so heated that the country singer released a statement in his own defense, claiming that he’s a Queen Bey fan, and he was simply enthralled by the show.  He also included that it saddened him that everyone made such a big deal over his facial expression, without coming to him first. Nothing more ever really came of it, and her fans took him for his word.

The 2018 CMA Awards

Chesney was scheduled to perform at the Country Music Awards, along with other big names in the business, like Garth Brooks, Miranda Lambert, and The Florida Georgia Line. As the telecast date rolled around, everyone got more and more excited about the prospect of seeing him perform at the show. But at the last minute, the CMA took to social media to release a statement letting everyone know that Kenny wouldn’t be able to make it that year.

The singer had lost someone in his family and canceled the show. While fans were (understandably) upset that they wouldn’t get to see him perform, they also understood his need to cancel and be with his family, and they flooded his social media to show their support in his time of need.

He’s Got the Best Body in the Biz

While it’s hard to say if his physique has much to do with the fact that he’s slept with over 100 women, including some of the most gorgeous ones on the planet, it’s definitely easy to say this: it’s an awesome bod. In fact, GQ called him the “fittest man in country music.”

The man does put a lot of effort into looking good, too. Not only does he basically run a mini-marathon every time that he performs, but he also likes to run on his treadmill. Apparently, that type of workout is too easy for super-fit Kenny, so he removed the belt so he uses his energy to move it instead. Ouch. Just picturing that makes our calves hurt. And like we mentioned previously when the star is on tour, he maintains a nutritious and well-balanced diet.

He’s Got a Liquor Line

It’s not unusual for celebrities to have different types of endorsement deals, where they lend their name to a product, so it flies off the shelves. But when Kenny decided that he wanted to have his own line of rum, he actually created one. The brand, Blue Chair Bay Rum, was designed by the star in pretty much every aspect, from the actual ingredients themselves to the appearance of the bright-green bottles.

The website even has several personalized recipes to make drinks that Chesney would drink himself, right in the comfort of your own home. It does seem fitting that the star, who likes to party and get his drink on. He often sings about his love of alcohol, like in his song Ten with a Two he sings, “last night downtown I was drinking booze like it was going out of style.”

If He Falls, He Gets Back Up

Chesney’s “down home country boy” act makes him seem a little rough and tumble, but that image may not be so far off from what he’s really like, after all. During one performance at a concert in South Carolina, there was an equipment accident that caused the singer’s foot to get caught between one of the lifts and the actual stage. Luckily, he got himself free in less than a minute.

He got right back to show and didn’t hold back a bit, regardless of the fact that he was limping and “obviously injured.” The singer is known to be a workaholic, so he obviously wasn’t about to let one little slipup get in the way of him entertaining his fans.

He’s Got an Insanely Huge Entourage

When the star goes on tour, he doesn’t leave a single thing to chance. He hires someone for every possible job you can imagine, to make sure that everything goes as smoothly as possible. But it can get incredibly expensive bringing over 100 people with you on every tour, although the star doesn’t mind footing the bill. Chesney has expressed how much he loves his life on the road, though, and says he wouldn’t trade it for anything (except maybe a chance to be a pro baseball player).

His crew basically forms a fleet on the tour, filling up dozens of busses at least. Chesney himself is usually on his private jet, whenever possible – a jet that he actually donated to some of his neighbors from St. Johns to escape hurricane Irma when it struck and devastated the little island community.

He’s Got a Big Heart

Even though Kenny may give off the impression that he’s this carefree playboy, he’s really got a huge heart, which shines through in his philanthropic endeavors. He supports a number of charities around the world, including Kids Wish Network, The National Parks Conservation Association, and MusiCares. He’s also been known for immensely helping out victims of hurricane Irma (among other major storms), and even filled his home in the U.S Virgin Islands up with people who needed a place to stay through the brunt of it.

He also established a non-profit for victims of the Boston bombing, the Spread the Love fund, which helped to raise money to cover medical bills for victims. Chesney has also saved numerous lives by finding bone marrow matches through holding pop-up, cheek swab donor match tests at his concerts.

Music is His Passion

They say follow your passion, and Kenny has definitely done just that. You can tell how much he loves what he does through his actions both on and off stage. He has often been called a perfectionist and workaholic when it comes to his music, but that’s because he cares a lot about all that he puts out there for his fans. Although some of his songs may seem a bit sad, it’s just because he uses his songwriting as a way to express himself and let out his feelings before they overwhelm him.

While some people may not be able to imagine a life on the road without a marriage or picket fence, that’s exactly the way Chesney prefers things. In fact, he’s said that he would probably be very unhappy if he had to live a “normal” life.

He Married Renée Zellweger

Although he may prefer the life of a bachelor, there was a point in Chesney’s life where he was actually married. Chesney met the award-winning actress, Renée Zellweger, early on in 2005 at a benefit concert. They dated for a few months and married later that same year. The country singer said that he knew that Zellweger was the girl of his dreams when he saw her in Jerry McGuire. In fact, he was so head-over-heels that he even wrote a song that he dedicated entirely to it called, “You had me at hello.”

But apparently Renée didn’t exactly feel as strongly, and the marriage only lasted for about 5 months before the two had it annulled. On the court papers, the reason Zellweger cited for the annulment was “fraud” – something that would spark a lot of baseless (and untrue) rumors about Chesney.

Bringing Joy to the World

Nearly every Kenny Chesney concert ends up getting sold out long before the show, prompting several hundred fans who couldn’t get their hands on a ticket in time to stand longingly outside of the venue and try to listen in as closely as possible. Luckily, when Chesney performed in 2012 for the American Express Unstaged concert at the Jersey Shore, he had an idea that would mean everyone would have a chance to see him live in action.

The singer partnered up with Jonathan Demme, an award-winning director, to create a special live-stream experience for his fans. The director sadly passed away a few years later, and Kenny took to social media to remember him, saying that he will never forget him.

He’s Very Humble

The 6-time Grammy-nominated musician may be extremely talented and travel the world with millions of dollars and a private jet and team of over 100 people but believe it or not – he’s still incredibly humble. Kenny grew up in a small town near Knoxville, in the heart of Tennessee. His father was a teacher in an elementary school, and his mother, a hairstylist. He got to where he is today strictly through his talent and drive.

In fact, he recorded and sold his own first album, and performed in local bars and venues around Nashville until he was discovered by someone from Broadcast Music. Chesney was never just handed anything on a silver platter, he worked for it, and it really shows in his positive outlook on life and music.

His Tractor is Definitely Sexy

If you’ve never heard the hilarious (yet, ridiculous) Kenny Chesney song, She Thinks my Tractor’s Sexy, you’re missing out! The song is a parody of some over-the-top country music, which plays upon country clichés like daisy dukes and shotgun weddings. Chesney told magazines upon the songs release that he recorded it in good fun and it obviously isn’t meant to be serious. After all, the star has a couple of tractors’, neither of which happen to fall into the “sexy” category.

Still, the comedic tune was a huge hit and made it all the way up to number 11 on the Billboard charts. But, even if the tractors themselves aren’t exactly “sexy,” it may be a different story when the country star is on one of them!

He’s Got a New Girlfriend

Chesney has been living it up as a bachelor ever since his heartbreak over his split with Reneê Zellweger. But recently, he’s been spotted with a new girlfriend on his arm quite frequently. There have been several reports of Chesney being seen with a gorgeous brunette, and the two have even been on an Italian vacation together.

For a while, no one even knew her name since the star likes to keep a low-profile, but the mystery woman has been revealed as Mary Nolan. Things have gotten pretty serious between the two, who have apparently been together since back in 2012, and there have even been some speculations that Kenny is planning on popping the question (of course, maybe not anytime soon.)

He Hates Being Sweaty

Chesney may love his workouts and spend a lot of time keeping his body fit, but that doesn’t necessarily mean that he likes to sweat. Some people love the feeling of sweating during a tough workout – Kenny is not one of them. In fact, he can’t stand the feeling of having a sweat-drenched shirt, which happens not only when he works out, but when he performs as well. After all, if you’ve ever seen him perform, you know how much he moves around!

So, what does the singer do to make sure he stays squeaky clean and dry? He showers multiple times per day and changes into clean clothes each time. But the country star refuses to use bar soap in his showers, as it creeps him out. He prefers to use some smell-good body wash instead.

He Wants a Hippy at Heart

He may be a millionaire and a clean-freak, but he’s looking for a woman who’s a little more carefree. In his song, “Wild Child,” he sings about his ideal type of girl. His perfect partner is apparently someone who’s got a lot of love but doesn’t care too much about shopping and trivial things like keeping her hair and nails done. And of course, as someone who loves himself a big old, greasy grilled cheese sandwich, he also wants her to love to eat just as much as he does!

He’s said during interviews that he wants anyone he dates to be intelligent and have a free-spirit. So basically, he is looking for an educated, cheeseburger loving Bob Marley fan.

He Made P!nk a Little Bit Country

P!nk isn’t really known to sing country-style songs, but rather her edgy, pop/punk style that’s taken her to stardom. She grew up in Pennsylvania and had a much different upbringing than the country star. But the two do share the fact that they both got into music at a very young age and worked their way up to where they are today. Over the years, Pink’s worked with some amazing artists, she even sang on the hit “Lady Marmalade,” with Christina Aguilera, Lil’ Kim, and Mya.

But in 2016, the musicians released a duet called “Setting the World on Fire,” in which Pink let’s go of her pop-style and tries out the country “twang.” Rolling Stone reports that the two singers are friends, and the prospect of the duet came up while they were hanging out in California.

Requests Anyone?

Chesney got his start playing at small venues around his college campus in Tennessee. Before he had compiled enough original songs to put out his own album, he used to play covers for tips in bars. He would put the tip jar next to the stage and take requests, with a sign taped to the jar that said something along the lines of “tips appreciated.”

But apparently, he’d been asked one too many times to play “Freebird,” because the sign also made sure to include the fact that any requests for Jimmy Buffet, Freebird or James Taylor would cost the requestor $25. After he graduated, he moved to Nashville where he played in some larger venues and was eventually scouted by a recording studio.

Sleeping with Sara Evans?

Sara Evans and Kenny Chesney actually have quite a bit in common, at least, regarding their careers. They’re both hardworking country-music stars who are passionate about performing and creating. However, Evans got married and had 3 children, while Kenny went the bachelor route. Unfortunately, things between Sara and her husband Craig didn’t work out, and they went through a pretty rough divorce. In court, things got pretty nasty when they each pointed the finger at each other for sleeping around.

The singer’s lawyer brought up the fact that Sara was sure her husband was sleeping with their maid, while Craig shot back that she was surely having an affair with Chesney, among others. Kenny shrugged the whole thing off, saying they were baseless and nonsensical accusations.

College Life

After the future country music star graduated from high school in 1986, he started on his 4-year university degree at East Tennessee State University in Johnson City. He decided to focus his efforts on communications and marketing – something that would serve him very well through his career!

To keep his head above water while he earned his degree, he would play at various bars and other venues around campus. Chesney never forgot about where he came from throughout his superstardom. In fact, he continuously gives back to his community. He even helped Eastern Tennessee State raise nearly $30 million so they could have a sports field put in.

No Shoes, No Shirt, No Problem

If you’re a part of Kenny’s fan club, you’re a part of the “No Shoes Nation.” The title that he gave to his devoted fans is based off his hit song, “No Shoes, No Shirt, No Problems,” which was released in 2002. The song is one of Chesney’s most popular of all time and topped the Billboard Charts for several months on end. The symbol of the fan club is the skull and crossbones (pirate style) and even appears on a huge flag that Kenny often pulls out at a performance and waves around as the audience cheers.

There are two tiers to the club, a free membership level, which includes bragging rights and access to the email newsletter which provides early announcements and pre-sales, and the premium level, which costs $25/month and provides members with first access to tickets before the general public or free members.

He’s Got a Crazy-Long Playlist

Good music is a lot like poetry, in a sense that it can’t be forced, but must naturally come to those who produce it. Kenny Chesney is one of the greatest musicians of all time, and he knows more than anyone what it takes to make good tunes. That means that he’s probably got an impeccable taste when it comes to what he listens to on his own time. The country singer has a playlist of hundreds of thousands of songs that would take literal weeks to listen to back-to-back.

If you’re curious about what kind of music the great Kenny Chesney listens to, he’s got his own station on Sirius XM radio called “No Shoes Radio,” which consists of only songs that he has handpicked.

He’s Got the Filmmaking Bug

Chesney is a multi-talented man with many interests and passions, some of which include music, sports, women, and anything to do with Tennessee – not necessarily in that order. He’s gotten his hands dirty in many aspects of the entertainment world and beyond. Aside from his many Grammy-nominated albums and songs, Chesney has also worked behind the scenes, making multiple documentaries for both film and television.

He produced and directed one documentary for SEC Storied called The Color Orange: The Condredge Holloway Story, about the first black quarterback in an SEC school. He also produced The Boys of Fall, which is a documentary film about some of the biggest names in sports.

Growing Up

As we’ve said previously in this article, Kenny Chesney by no means had anything handed to him. He had to work his butt off to make it to the superstar status he holds today. But it wasn’t like his childhood was too rough. In fact, it was pretty adorable and exactly what you’d imagine when you think of a Southern upbringing. The star was raised in a small town east of Knoxville Tennessee, in a tight-knit family that included his mom and dad and his sister, Jennifer.

He talks about how close his parents were and how things were for him growing up in his song, “Where I Grew Up,” a song that he exclaims is the kind that you “hope to get at least 3 times in your entire career.” Even after he graduated high school, he stayed within his home state and moved a few hours away to Nashville – home of the country music stars.

College

One thing Kenny Chesney never lacked was the drive to accomplish great things. This drive started when he was young and knew that music was what he wanted to do. He started to make things happen for himself in high school by working hard in his academic commitments. Then, he brought that drive with him to college when he enrolled at East Tennessee State. He linked up with a band and played covers in different venues around campus, really making a name for himself in the local college community.

He also joined up with the Lambda Chi Alpha fraternity and the ETSU Bluegrass Program. All the while, he pursued his 4-year degree in advertising, which would really come in handy for him later on down the road. He was so grateful to his alma mater that once he’d made his fortune, he started up a foundation to help them raise the money for a new arena.

He’s Super Independent

Tons of musicians are born into the industry or get hooked up because their parents know someone big when they’re young and they happen to get their foot in the door with mega-producers before they even hit the age of 18. But in Kenny Chesney’s case, he took matters into his own hands to create the life that he wanted for himself, he didn’t wait around for someone to give it to him. When he was just 21 years old, he recorded his very first album with a guitar that he’d been given for Christmas in college.

He wound up selling nearly 1,000 copies of the album and used the proceeds to buy himself another, newer, nicer guitar. That guitar was basically Chesney’s baby, and music, his one true love. He used that guitar and followed his heart straight to the top.

He’s Made a Ton of Albums

Chesney graduated from East Tennessee State in 1990 with his degree in advertising. Afterward, he headed out to Nashville to really get his foot in the door in the music and entertainment industry. When he was playing a set in one of the blues clubs, he was scouted by the head writer of relations from BMI and invited to record his first major record. In 1994, Chesney’s In My Wildest Dreams album debuted. About 20 years later, and he has now put out 20 major albums, 14 of which have made it to gold status.

In addition to his albums, he’s also made top 10 on the Billboard with 40 of his singles. 29 of those singles even made it all the way to number 1! In 2018, he ended his recent Sony Music contract and signed with Warner Brothers. Later that year, he put out his most recent album, Songs for the Saints.  The king of country has sold more than 30 million albums internationally since the start of his career.

…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’s Friends with Tim McGraw

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.

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!

No Shoes, No Trash Bags

Weeks before the Kenny Chesney concert rolled into Philadelphia in 2016, the Three Rivers Power Sweep cleanup company was planning on extra manpower to handle the trash nightmare they knew would be left behind. Why? Because according to the company’s owner, it’s the biggest trash cleanup that the company faces, and it’s happened now for more than 6 years in a row. Fans tailgating at the North Shore left behind over 50,000 pounds of garbage, in the form of broken chairs, beer cans, water bottles and more.

One man that works for the trash company claims that he’s lost a whopping 10 tires to the broken glass left behind from all of the alcohol consumed at Chesney’s shows. The event has outraged locals to the point that they started a Facebook page with the hopes of getting the country star and his concerts banned from the city for life. But the trash isn’t the only problem the fans had pre-show. The drinking got so out of hand that over 70 people were arrested and 25 were taken to the hospital for injuries.

The Rumor Mill

Remember when we said that Reneé Zellweger had “fraud” outlined as the reasoning behind her annulment from the country star after their brief marriage back in 2005? Well, when the media got a hold of that, rumors started to circulate as to what that could have possibly meant. Some speculations even went so far as to say that the star was gay, even though he had been publicly seen canoodling with dozens of women.

Zellweger hit back against the rumors, putting out a statement saying that the word was simply “legal slang” and didn’t have anything to do with Chesney as a person. She also said that she doesn’t like that people are saying “gay” as if it is something negative. Chesney laughed the rumors off, not giving them but a second of his time. After all, he does have about 100+ women who can set the record straight about that one.