Little Known Facts About Country Music Legend Kenny Chesney

Published on 11/06/2018
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Kenny Chesney is definitely considered to be one of the greatest country singers. Despite the fame, however, not everyone knows who he actually is. You might be surprised to learn that there is a lot hiding under that cowboy hat.

More Than Meets The Eye

It is not unusual to find Kenny Chesney talking about his past relationships. Just like other musicians, he has penned songs about the people he has dated before. However, there is more than what his songs let on…Keep reading to find out all about the life of this talented country performer!

More Than Meets The Eye

More Than Meets The Eye

9/11/2001

Whatever faith Kenny might have, we are sure he believed in miracles when he was spared from the tragic 9/11 attack. Around that time, his band planned to go to NYC to make a music video at the World Trade Center. Luckily, the shoot had been canceled at the last minute, moments before the skyscrapers went down. Upon realizing that he had been saved, Kenny said, “It really makes you believe that there’s something up there…” This was definitely a life-changing moment for him.

9/11/2001

9/11/2001

Chesney’s Tailgates

His concert venues are usually huge stadiums, though there has never been any problem filling out his shows. The pre-show tailgates are always thrilling, and you will never fail to see hordes of fans excited to see him. Sadly, the Pittsburgh concert crowd in 2016 took things a little too far. The fans got too rowdy and intoxicated – 25 people were hospitalized, and there were even some arrests. This was rather similar to a concert in 2013 where there were 73 arrests and 30 tons of accumulated trash! These were devastating events, though we’re glad his loved ones stuck by him throughout these trying times.

Chesney’s Tailgates

Chesney’s Tailgates

More Partners Than A-Rod

Kenny is well known for his love songs, and it would be hard to top “You Had Me From Hello.” The hit was inspired by Jerry Maguire’s famous line, and the tune is definitely romantic. However, this musician was much naughtier than what his songs would have you think! There are plenty of pictures of him spending time with different lovers as well as hanging out at the Playboy Club. He has claimed that he has been with more than a hundred women! He said, “There were years when I had a better summer than A-Rod, buddy. You know? I got on the boards quite often.”

More Partners Than A Rod

More Partners Than A-Rod

Involved In A Kanye And 50 Cent Dispute

Hip-hop fans will know that it is not unusual for the rappers 50 Cent and Kanye West to get into some sort of beef with each other. In fact, the two musical stars held a public contest to find out whose newly released album would end up selling more copies. 50 Cent took the risk and promised to retire if he loses. The pair were already heated, though Kenny found himself in the middle of the argument when he announced that he would also be coming out with an album on the same day. Sadly, Kanye won and Chesney ended up in the third spot.

Involved In A Kanye And 50 Cent Dispute

Involved In A Kanye And 50 Cent Dispute

Stole A Sheriff’s Horse

Kenny and Tim McGraw worked together during the George Strait Country Music Festival held in upstate New York. The country musicians spent time in the parking lot talking to each other. That was when they saw a sheriff with a horse! Kenny already had his riding boots on, and he asked for permission to ride the stallion. The officer gave him the go signal, and Kenny hopped on the horse before riding off into the distance! When he was asked to stop, Kenny did not turn back. They were arrested for the whole fiasco, although the charges were dropped later on.

Stole A Sheriff’s Horse

Stole A Sheriff’s Horse

Dated Miss Tennessee

Kenny was not in the best position after he got divorced. Luckily, he met a burn-unit nurse and former Miss Tennessee named Amy Colley. He was able to get his game back, and Amy became the next woman to call him her boyfriend. They were photographed many times as they enjoyed holidays along the beaches of Malibu and the Bahamas. The relationship later got more serious as evidenced by the fact that they spent Thanksgiving vacations with each other’s families. However, we think the biggest indicator of how serious things were would be the fact that Kenny let her drive his truck!

Dated Miss Tennessee

Dated Miss Tennessee

Cheated On Miss Tennessee?

Sadly, the relationship eventually began to fall apart, and it seems like the last straw was Chesney’s suspected infidelity. He was seen spending some time in Cancun with another woman, Jenn Brown. She started out as a collegiate athlete before making it big as an ESPN broadcaster. She is not an unusual sight to see on the sidelines of football games. She made a name for herself when she became the first female correspondent for Inside The NFL. Amy and Kenny had been together for two years then, and she was devastated when she learned about the affair.

Cheated On Miss Tennessee

Cheated On Miss Tennessee

Oops: Thought The Cop Was Dead

Officer Christopher Dorman landed in the hospital when he took part in a huge drug bust. He was shot a total of seven times, and he had to be treated by medical professionals. This was why he did not get to attend the Kenny Chesney concert he wanted to attend that same night! Upon learning of the incident, the musician decided to honor him by talking about the officer in front of the 70,000 concertgoers. However, Kenny got carried away and said the officer passed away, though he later apologized to Dorman and even invited him to grab a beer.

Oops: Thought The Cop Was Dead

Oops: Thought The Cop Was Dead

Highest Paid Lists

A lot of people want to become a rock star, though not everyone gets around to doing this. Fortunately, Kenny was one of those people who was able to build a career by doing what he knows and loves. Forbes even said that Kenny is the 53rd biggest-earning celebrity in the world with an annual income of $42.5 million! When it comes to musicians, meanwhile, he ranks higher up at the 18th spot! He likes to spend his earnings on adventures, though he also donates money to charity groups like The Salvation Army and Farm Aid.

Highest Paid Lists

Highest Paid Lists

White House Performance

During the administration of George W. Bush, Kenny was invited to a state dinner with John Howard, the Australian Prime Minister. The POTUS wanted Kenny Chesney to serenade the guests and perform at the event. As a gesture of gratitude, Bush gave the country star a pair of cowboy boots made with eel skin that had been designed by the talented Rocky-Carroll. They were even engraved with Kenny’s initials, as well as the flags of both the United States and Australia. The musician and the former head of state met again when Kenny performed the national anthem during the 2008 White House Tee Ball All-Star Game.

White House Performance

White House Performance

Reese Witherspoon Paid To Sing With Him

Charity-givers and music-lovers got together during the New Orleans House of Blues to help support the charities of celebrities Matthew McConaughey and Drew Brees. TMZ reported that Reese Witherspoon pledged $24,000 to the charities in order to snag the opportunity to sing a duet with Kenny Chesney. Together, they sang “Jackson” by Johnny Cash, and the actress was highly prepared for this as she won an Academy Award for her portrayal of June Carter Cash in Walk The Line. She did miss a word every now and then, though the crowd loved the performance regardless.

Reese Witherspoon Paid To Sing With Him

Reese Witherspoon Paid To Sing With Him

Never Give Up

A lot of artists know what rejection feels like. It can happen at any point in their career for whatever reason, though it is particularly common in the beginning. Keep in mind that while it hurts when someone undermines you, they also help make you stronger. Nowadays, Kenny composes love songs and makes women swoon with his music. Isn’t hard to believe that a girl once rejected him, even after he wrote her a song? That was the first time he experienced rejection regarding his music, but needless to say, he did not give up!

Never Give Up

Never Give Up

Thank You To The Crew

You will constantly find Kenny touring, and he will always be accompanied by a 120-employee team every time. He hires them to take care of the driving, planning, and equipment. It must be difficult running everything on your own, and this is why Chesney makes sure to take care of his workers. Apparently, he lets a lottery decide which member of the crew receives the profit from the merchandise sales. Once, it even reached $300,000! Moreover, he also lets his employees take week-long vacations after every big tour.

Thank You To The Crew

Thank You To The Crew

Strict Diet During Tour

You might think that he’s a carefree person because he spends his free time on the beach, though that’s not actually true. In fact, Kenny is incredibly strict when it comes to his diet when he is on tour. Whenever he is on tour, Kenny stays fit by eating a huge amount of veggies and chicken. When it’s off-season, however, this does not apply. During this time of the year, Kenny is free to eat as much junk food as he likes!

Strict Diet During Tour

Strict Diet During Tour

Tests Nosebleed Section

When you want to know more about his career, the first thing you will have to know is that Kenny is a workaholic. He makes sure to check every last detail before his shows since he wants the fans to have the best experience. Before he performs in large venues, Kenny walks to the nosebleed section to see what the sound is like over there. When he does this, he estimates how much energy he needs to expend to move someone who is seated in that section. According to the musician, the happiness of the nosebleed fans is a good indicator of the happiness of the whole crowd.

Tests Nosebleed Section

Tests Nosebleed Section

Green Room Is A Box?!

Anderson Cooper had the opportunity to take a look at Kenny’s pre-concert rituals, and it was definitely not what he had in mind. The green room, for one thing, isn’t the regular fancy are complete with free-flowing martinis and leather couches. Nope, Kenny typically waits inside a small box of a room just big enough to fit two people inside. From there, Kenny would be wheeled to the stage area where he would appear and take the audience by surprise.

Green Room Is A Box?!

Green Room Is A Box?!

Wanted To Be An Athlete

We are sure that Kenny truly enjoys what he does. There is no doubt in our mind that he is passionate about singing and playing music. However, you should know that things weren’t like this in the beginning. When he was younger, he wanted to play second base for his favorite baseball teams, the Boston Red Sox or the Cincinnati Reds. As we all know, he decided to make a career out of music instead, though at least he gets to perform during major baseball games!

Wanted To Be An Athlete

Wanted To Be An Athlete

Got First Guitar On Christmas

As a little boy, Kenny Chesney loved Tennessee stars, and he wondered if there was anything beyond the country boundaries. At that point, he had already been dreaming big and things changed when he got a guitar for Christmas. He called it the “Terminor,” and he studied how to play the instrument on his own. It completely changed his life and shifted his focus from sports to music. With Terminor in hand, Kenny embarked on a new adventure by serving as the resident musician at nearby clubs.

Got First Guitar On Christmas

Got First Guitar On Christmas

Attacks From Beyoncé Fans

In 2016, Beyoncé and the Dixie Chicks appeared together for a performance at the Country Music Association Awards. It was incredible, it goes without saying. However, as the camera closed in on the celebrities from the seats, Kenny was caught making a displeased face. Social media noticed and shamed him for it. He even had to come out with a statement in order to redeem himself. He mentioned that he was only focusing on watching the performance as a Beyoncé fan, and he was sad about the harsh reception to his expression.

Attacks From Beyoncé Fans

Attacks From Beyoncé Fans

Insane Drive To Be Physically Fit

Kenny might have had to set aside his dreams of becoming a professional athlete, though he has never forgotten to prioritize his fitness. When you add the total number of steps he takes in a performance, you will know that he actually takes several miles up there! He stays in shape by going on a treadmill – one that doesn’t have a moving belt and is solely powered by his feet! On the other hand, his guilty pleasure is a hot, grilled-cheese sandwich. He forbids himself from having any when he goes on tour!

Insane Drive To Be Physically Fit

Insane Drive To Be Physically Fit

Own Line Of Rum

Instead of choosing to sign a deal to have some company produce rum and stamp his name on it, Kenny Chesney decided to build his own company from the ground up. He decided to launch his own business because he is particular about how he wants things done, and he wants to know the nitty-gritty of it all. The alcoholic beverage is called Blue Chair Bay Rum, and it comes in a bright green bottle. It is safe to assume that the country musician is involved with every step of the process, from the aesthetics to the ingredients.

Own Line Of Rum

Own Line Of Rum

Injured During Concert

During a show held in South Carolina, he got injured thanks to a stage equipment mishap. As he was singing the third song, his foot got stuck between the stage and a lift. The musician was trapped there for half a minute! He was able to free himself and go back to sing, although the fans could tell that he was injured. Kenny was motivated to keep going thanks to his desire to please the fans and the overflowing adrenaline in his body.

Injured During Concert

Injured During Concert

An Enormous Crew

Whenever he embarks on a tour, it is considered serious business, and it involves a huge convoy. His tour crew comes with eight buses and seventeen semi-trucks loaded with equipment. It seems like Kenny feels overwhelmed by it all at times, and he has mentioned, “You could only imagine what diesel fuel costs me as an overall expense for this year.” Intense is one way to describe it, though Kenny does love this way of living. Again, he is meticulous and he even chooses the color of the bus!

An Enormous Crew

An Enormous Crew

Philanthropy

Kenny is considered one of the wealthiest country celebs ever and this status has let him give back to numerous non-profit organizations. He has established the Spread The Love Fund in order to pay for the medical bills of the Boston Marathon bombing victims. Apart from making monetary donations, he has also paid visits to the injured when they were at the hospital. He even raised awareness by letting fans register to donate their bone marrow during concerts. His 2015 tour possibly saved 25 lives courtesy of the stadium registration system he initiated.

Philanthropy

Philanthropy

His Mistress

Anyone familiar with Kenny Chesney will let you know that he puts in a lot of passion and drive in whatever he does. Even when he has finished climbing new heights, he feels the need to do even better. He has talked about how he is similar to a shark in the way that he needs to be constantly on the move to stay alive. Composing songs has helped him cope with stressful circumstances and he has harnessed these feelings into the creation of his greatest hits. He has said that he is content to be a single man with music for a muse.

His Mistress

His Mistress

Live-Stream Concert

It is important for him to create an intimate atmosphere for the fans, and this is why he tries to reach as many fans as possible during his shows. In order to do so, he once streamed a New Jersey show for the entire world to witness. He was able to take the Jersey shore to everyone’s screens with the help of director Jonathan Demme. Five years after the filmmaker’s death, the musician said he will forever remember Demme’s ability to capture his music using film without losing either the energy or the heart.

Live-Stream Concert

Live-Stream Concert

Humility Of The Millionaire

Kenny is well known for being a humble and down-to-earth fellow. Rolling Stone even said that the country musician “wears his fame very lightly, if at all.” It seems like there is some truth when Kenny talks about feeling most at home in a Virgin Island burger joint! Not just in the store itself, but also in its back alley, where they keep the ice-makers and the propane tanks. This is what he has claimed to be his happy place, aside from his own executive suite.

Humility Of The Millionaire

Humility Of The Millionaire

Attractive…Tractor?

Many people like to make fun of country music because they think it is all about rambling on about one’s cowboy boots and pickup trucks. Kenny supported the stereotype when he came out with “She Thinks My Tractor’s Sexy.” He was well aware that the song was silly and he said, “I was smart enough to record that song but I was smart enough also not to record another one.” While Kenny does own two tractors, he does not find them to be “sexy.”

Attractive… Tractor?

Attractive… Tractor?

Current Girlfriend Mary Nolan

We have not heard a lot of things about his present dating life, though perhaps this has something to do with the way the media ridiculed his short marriage. When he was particularly quiet about his private life, the rumor mill started spreading that he was seeing Miranda Lambert, though there seems to be no truth to it. However, he did take a gorgeous date to the American Countdown Awards. The brunette is none other than Mary Nolan, though we don’t have any other information about her!

Current Girlfriend Mary Nolan

Current Girlfriend Mary Nolan

Three Showers Per Day

On a normal day, you will likely find Kenny doing any of these things: relaxing on the beach, working out, or performing on stage. If you think that this sounds like the sweet life, you are not entirely correct. Apparently, he avoids activities that will make perspire because he hates the feeling of sweat. He is actually a clean freak who likes to take three showers a day. He prefers using body wash over soap to ensure that he isn’t sticky and reapplies deodorant to ward off any stench.

Three Showers Per Day

Three Showers Per Day

Loves Free Spirits

Kenny is not a fan of the objectification of women, and this was how he came to write “Wild Child,” a song that describes “his kind of girl.” The song talks about the way his heart is captured by a free spirit that keeps her hair messy and looks decadent in thrift store finds. The lyrics also go well with the statements he has released about wanting a lover who is bohemian, smart, and carefree. Interestingly, he also mentioned that the ideal partner should be a food-lover.

Loves Free Spirits

Loves Free Spirits

Turned Pop Star P!NK Country

True enough, Pink is not your regular farm girl from Alabama. She does not seem like the type to have grown up with country music, cold beers, and dusty roads. However, she has successfully collaborated with various artists from different parts of the planet. She has worked with Steven Tyler, Naughty By Nature, and Eminem. She worked with Kenny on a song titled “Setting The World On Fire,” which appeared on his album Cosmic Hallelujah.

Turned Pop Star P!NK Country

Turned Pop Star P!NK Country

$25 For Freebird

When he was just learning how to play the guitar, he did not have plenty of original songs he could play yet so he had to resort to doing covers. Back then, he played a lot in the bars near his college campus, and he would place a tip jar nearby. He wanted to avoid certain requests, and this was why he taped a sign that read, “Tips welcome, but anything by James Taylor, Kimmy Buffet, or especially Free Bird is $25.” He did not have any particular issue with these artists, he was simply sick of getting the same requests again and again!

$25 For Freebird

$25 For Freebird

Affair With Sara Evans?

Just like Kenny, Sara Evans is also a country singer-songwriter who enjoys what she does for a living. She tied the knot with Craig Schelske, and they welcomed three children into the world. They later got a divorce and accused that the other had cheated. The accusations started when she accused Craig of taking the housekeeper to bed. Meanwhile, Schelske fired back and alleged that Sara had 11 affairs of her own and the list included Chesney. Kenny only had this to say about the accusation: “Ridiculous.”

Affair With Sara Evans

Affair With Sara Evans?

College Is Important

After graduating from high school, Chesney matriculated at East Tennessee State University where he took up advertising. College proved to be an important part of his personal development as this was when he learned to take care of himself. According to him, this was when he first realized nobody could bail him out of living. In an effort to give back, he helped the university raised funds for a stadium. Only half a year after the announcement, his alma mater already reached 75% of their $26.6 million funding goal.

College Is Important

College Is Important

No Shoes Nation

“No Shoes Nation” is the name that one of his fan bases goes by. It is a reference to his song “No Shoes, No Shirt, No Problems.” The people who founded it also made a symbol for the faction, and it came with the trademark skull and crossbones of pirate flags. During a performance, he saw a hairless girl, a cancer patient, and took her to the stage. He serenaded her with, “Every little thing is gonna be alright.” The crowd was completely speechless and many concertgoers were in tears. He’s truly in a league of his own.

No Shoes Nation

No Shoes Nation

Three Weeks Of Playlists

Music is not something anyone can make with a simple finger snap, and the same is true for Kenny. Lyrics come when inspiration hits, and the mood needs to perfect to bring something beautiful to life. It apparently takes three weeks of non-stop playing if you wish to go through every song in his music collection! Whoa. Apparently, his music collection has been sorted by playlist as he has one for every occasion you can think of. He actually prepared a pre-show playlist to hype him up, and it’s full of songs by groups like Aerosmith and AC/DC.

Three Weeks Of Playlists

Three Weeks Of Playlists

Made Two Documentaries

Like we said before, Kenny adores two things: sports and Tennessee. He was able to combine his two passions by creating a documentary called The Color Orange that focuses on Condredge Holloway. The University of Tennessee star quarterback has an inspiring story as the grandchild of a former slave. Did you know that he was actually the first African-American quarterback to have started in the Southeastern Conference? It’s true! Chesney has also produced another documentary titled The Boys Of Fall, which involved interviews of his sports heroes.

Made Two Documentaries

Made Two Documentaries

Four Month Marriage To Renée Zellweger

Kenny Chesney and Renee Zellweger’s relationship had been so short that the latter has actually forgotten parts of it! She lamented, “It’s a pretty big thing to forget, isn’t it?” They first met during a fundraiser for tsunami relief, and they got married soon after. Sadly, they decided to annul their marriage after only four months. Chesney has this to say about the matter: “I didn’t have any clue as to what true marriage meant. I was so used to committing to one thing- music- and then I had to totally commit to a second thing, marriage.”

Four Month Marriage To Renée Zellweger

Four Month Marriage To Renée Zellweger

In The Beginning…

The path he took towards success had been a bumpy one, and we can trace it all the way back to his birth on March 26, 1968. Kenny was born at St. Mary’s Medical Center in Tennessee to a hair stylist and a primary school teacher. He has a little sister named Jennifer Chandler and the pair grew up together. Their parents instilled humble values in them, that much is certain. He had a pretty ordinary upbringing, and this was what kickstarted his journey to stardom.

In The Beginning…

In The Beginning…

College Years

When it comes to education, Kenny had always been an achiever. Of course, the same can be said for his extracurricular activities. When he was a teenager back in the 80’s, he was a huge sports fan and even played on his school’s football and baseball teams. When he went to college to study advertising, he was given a fantastic Christmas gift that completely changed his life. We are talking about “The Terminor,” of course. It was his first guitar, and it is even more amazing when you consider the fact that he was self-taught!

College Years

College Years

First Try At Music

Kenny recorded his first demo record just before his college graduation. He practiced for innumerable hours and built a reputation by playing at the local bars. Impressive, he was able to sell a thousand copies of his first album! Using the money he earned, he was able to buy a new guitar that he then took everywhere. After this, he decided to move to Nashville in order to expedite his music career. This was where he got his big break, of course.

First Try At Music

First Try At Music

So Many Albums

After he was able to establish himself in Nashville, Kenny Chesney kept climbing the ladder of the country music industry. The 1994 album titled In My Wildest Dreams was his first one released by a major label. He released 17 other solo albums all in all, the most recent of which is the 2018 album, Songs for the Saints. Additionally, he also created several Greatest Hits albums, as well as, two live albums, Live: Live Those Songs Again and Live In No Shoes Nation.

So Many Albums

So Many Albums

Award Winner

His reputation as a country musician has gone up so high that he even received support and admiration of numerous critics and institutions. Exactly a decade after he first released an album, he received a nomination for the Best Country Collaboration With Vocal at the Grammys. Over the course of his career, he was nominated for five other Grammys! The most recent accolade he earned was when Cosmic Hallelujah took home the Best Country Album during the 2007 Grammy Awards.

Award Winner

Award Winner

Crazy Net Worth

With millions of record sales, many sold-out tours, and making a name for himself, Kenny has truly become one of the most popular and well-paid performers in the industry. In all honesty, we did not find it surprising to hear that he has one of the highest net worths in the field of country music. In 2015, Forbes reported that his annual income comes up to approximately $42 million. We bet he used to think this was impossible! By 2018, his net worth is believed to stand at $225 million.

Crazy Net Worth

Crazy Net Worth

Buddies With Tim McGraw

When you hear their names mentioned together, you will likely remember the wild horse story we previously mentioned. However, there are other things they have done together. Of course, there was the time when these two co-headlined a tour side by side. The Brothers of the Sun Tour saw these two come together once more to tour 22 venues! The tour was able to gross a whopping $96 million in ticket sales. This means that more than a million people attended the shows!

Buddies With Tim McGraw

Buddies With Tim McGraw

Question About Orientation

When Zellweger and Chesney separated, they decided to go with annulment with “fraud” as the legal basis of the separation. The claim was not precise, though it was probably because fraud appeared to be the least harmful option they had. After they called it quits, the media began suggesting that the country musician was actually gay. Renee explained, “It was simply legal language…not a reflection of Kenny’s character.” Meanwhile, Chesney only replied to these rumors by saying, “I’ve got a long line of girls who could testify that I’m not gay.” What a legend!

Question About Orientation

Question About Orientation

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