Kenny Chesney Finally Gets Candid About His Love Life


Kenny Chesney is one of the most successful country singers on earth, but he hasn’t been as successful in love as he has been in music. Now, the music sensation is getting candid about his personal life.

Dated Miss Tennessee

After going through a divorce, Kenny Chesney wasn’t in the best shape. Thankfully, he met Amy Colley, a burn-unit nurse and also Miss Tennessee 2005. Reviving his spirits, Amy was the next lucky woman to call Chesney her boyfriend.  The two were spotted many times happily vacationing on the clear beaches of the Bahamas and Malibu. The relationship eventually became serious and they even took each other to Thanksgiving vacations with one another’s families.

Dated Miss Tennessee

Cheated On Miss Tennessee?

With Kenny and Amy’s relationship slowly falling apart, the final straw was when Chesney was spotted hanging out with another woman in Cancun, Jenn Brown. Starting as a Division 1 college athlete, Jenn eventually made it to becoming a successful ESPN broadcaster and she has been on the sidelines of many massive college football games as well. She made history when she became the first female correspondent of Inside The NFL. After being Kenny’s devoted lover for two years, Amy was devastated when she found out about him and Jenn’s affair.

Cheated On Miss Tennessee?

Oops: Thought The Cop Was Dead

Officer Christopher Dorman was taken off guard when he participated in a big-time drug bust. After being shot seven times, Dorman ended up in the hospital and missed out on the Kenny Chesney concert he planned on attending that night. When Chesney heard about the incident, he paid tribute to him by mentioning him in front of the 70,000 fans who were standing in Lincoln Financial Field. He got carried away when he said the officer had passed, but later made it up by apologizing to the officer and inviting him for a beer.

Oops: Thought The Cop Was Dead

Highest Paid Lists

Many people dream of becoming a rock star, but few actually get to achieve the riches and fame that come along with it. Luckily, Kenny was one of the fortunate few who managed to create himself a career doing what he loves. According to Forbes magazine, Kenny is the 53rd highest-earning celebrity in the world, earning $42.5 annually. If you count just the musicians on the list, Forbes has Kenny at 18th in the world. Although he enjoys spending his money on awesome adventures, he still gives charity to groups like Farm Aid and The Salvation Army.

Highest Paid Lists

White House Performance

When George W. Bush was president, he was invited to attend a state dinner with the Australian Prime Minister, John Howard. Wanting to serenade them, Bush invited Kenny Chesney to perform at the event. After the show, Bush presented the country star with a pair of eel-skin cowboy boots, specially designed by the famous Rocky-Carroll. The shoes were customized with engravings of Kenny’s initials and the flags of Australia and the U.S. Bush and Chesney met once again when Kenny sang the national anthem in 2008 at the White House Tee Ball All-Star Game.

White House Performance

 

Reese Witherspoon Paid To Sing With Him

Music-lovers and charity-givers gathered excitedly together at the New Orleans House Of Blues to give support to the charities of celebrities Drew Brees and Matthew McConaughey. According to TMZ, Reese Witherspoon donated $24,000 to the charities just to join Kenny Chesney and duet with him. They sang an acoustic version of “Jackson” by Johnny Cash, which luckily, Witherspoon was prepared for, as she previously got an Oscar for playing June Carter Cash in Walk The Line. All though she forgot a few words here and there, the crowd enjoyed her performance anyway.

Reese Witherspoon Paid To Sing With Him

Never Give Up

Most artists experience rejection at some point in their career, especially in the beginning. When someone doubts or undermines your talents, it does hurt, but it also makes you stronger. Nowadays, Kenny writes love songs and woos women with the alluring sounds of his deep voice and classical guitar. Before he got famous, he wrote a song for a girl he liked, but she rejected him anyway. This was the country star’s first taste of rejection with his music but he kept his head held high and kept trying. And look where he is today!

Never Give Up

Thank You To The Crew

Kenny is constantly on tour and you’ll always find him with a 120-employee team which he brings along to help with the planning, equipment, and driving. It’s hard work making sure everything runs smoothly, so Chesney tries to give back to his workers. He makes a lottery to decide which crew member gets the profit from the merchandise sales, and they once got $300,000. To top that off, he takes his employees on vacations for a week of relaxation after each big tour.

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Thank You To The Crew

Strict Diet During Tour

Just because Kenny spends much of his time laying on beaches, it doesn’t mean he’s totally carefree. You may be surprised to hear that Kenny is actually very strict about his diet – while on tour, that is. During his off-season, it’s a different story. Kenny says that during tours he keeps fit by eating a diet that includes a large amount of chicken and veggies. When it’s off-season time, Kenny doesn’t think twice before grabbing a bag of Pringles off the snack shelf.

Strict Diet During Tour

More Than Meets The Eye

Kenny Chesney has often been quoted talking about past relationships. Like most singers, the country star has written songs about the women he’s dated. But there’s a lot more than what you find out from the songs…

More Than Meets The Eye

More Partners Than A-Rod

Kenny is noted for having a special knack for love songs, especially “You Had Me From Hello.” But it turns out, the southern artist is a lot naughtier than “lovey-dovey.” He has been photographed with countless different lovers and has even been spotted chillin’ at the Playboy Club. Aside from bragging about being with over 100 women, was there any he got “the feels” for?

More Partners Than A-Rod

Stole A Sheriff’s Horse

After the George Strait Country Music Festival in upstate New York, where Kenny and Tim McGraw collaborated, the two musicians stood in the parking lot, lightly chatting. Suddenly, they spotted a sheriff, accompanied by a horse, and with Kenny’s riding boots already on, he couldn’t help but ask to sit on the officer’s stallion. After receiving permission, he hopped on the horse and rode off into the distance. Despite the Sheriff ‘s pleas for him to stop, Kenny didn’t turn back. The two were arrested, but the charges were eventually dropped.

Stole A Sheriff’s Horse

Tests Nosebleed Section

If there’s one word Kenny uses to describe himself, it’s “workaholic.” He goes over every detail before his concerts, making sure that fans will get the best experience possible. Before performing in large stadiums, Chesney walks up to the nosebleed section to test out the sound there. By doing this, he can get a better idea of how much energy he has to put in in order to touch someone sitting all the way up there. Kenny says that if the nosebleed fans are pleased with the music, the rest will be too.

Tests Nosebleed Section

Green Room Is A Box?!

Journalist Anderson Cooper got a behind-the-scenes look at Chesney’s pre-concert routine and it was certainly NOT what he expected. The backstage green-room isn’t a fancy place with leather couches and all-you-can-drink martinis. Instead, Kenny waited inside of a tiny box, just large enough to fit him and Anderson inside. They were then secretly wheeled towards the stage, where Kenny appeared out of nowhere and surprised the unsuspecting audience. And all this was in time for the opening song.

Green Room Is A Box?!

Wanted To Be An Athlete

There’s no arguing Kenny loves what he does and was meant to do it. Singing and playing instruments is obviously something he deeply resonates with, but this wasn’t always the case. In Kenny’s younger years, he dreamt of playing second base for either the Cincinnati Reds or Boston Red Sox, which are his two favorite teams. Although Chesney’s career ended up revolving around music, he still gets to perform at major baseball games, so we think he’s just fine.

Wanted To Be An Athlete

Got First Guitar On Christmas

As a young boy, Kenny admired Tennessee stars and wondered if anything existed beyond the country line. He was already dreaming big and his life took a turn when he received his first guitar on Christmas Day. He named it, “Terminor” and taught himself how to play. The guitar changed his life dramatically, shifting his career focus from sports to music. With Terminor by his side, Kenny was able to embark on a musical adventure, playing as a resident musician at local clubs.

Got First Guitar On Christmas

Tragic Loss

When Kenney Chesney proved unable to make it to the 2018 Country Music Awards, the organizers knew the show must go on, but wanted to express their deepest sympathies for the star. Tragically, one of his close family members had passed away, and Chesney was consumed by his grief. The statement CMA issued on its Twitter page read, “CMA Musical Event of the Year winner & Entertainer of the Year nominee @KennyChesney will be unable to appear on tonight’s telecast due to a death in the family.”

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Tragic Loss

Attacks From Beyoncé Fans

In 2016, the Dixie Chicks and Beyoncé performed together at the Country Music Association Awards show and it was absolutely incredible. However, when the camera was cutting to celebrities in the crowd, they caught Kenny Chesney with a rather sour face. Social media shamed him to the point that Chesney had to release a statement to redeem his reputation. He stated he’s a genuine Beyoncé fan who was simply focused on watching the show and was saddened by the media’s harsh response to this.

Attacks From Beyoncé Fans

9/11/2001

Kenny was given a reason to believe in guardian angels when he was miraculously spared from the 9/11 attack. His band planned on journeying to NYC to shoot a music video in the World Trade Center, but the shoot was canceled last-minute, just before the two skyscrapers crumbled. When Kenny realized he was saved, he said, “it really makes you believe that there’s something up there…” From that day, he was even more grateful for everything he had.

9/11/2001

Insane Drive To Be Physically Fit

Although Kenny put his dreams of becoming an athlete aside, he still makes an effort to keep healthy and look as fit as possible for his tours and performances. If you add up his steps during a performance, Kenny runs many miles on the stage. He keeps in shape by running on a treadmill that doesn’t have a moving belt, but is instead powered by his running. Kenny’s guilty pleasure is a steamy grilled cheese sandwich, but he doesn’t allow himself to eat it while on tour.

Insane Drive To Be Physically Fit

Own Line Of Rum

Instead of signing a deal with a company to produce rum with his name on it, Chesney created a company of his own. Because he’s particular about the way he wants things done and concerned with small details, he decided it would be a better idea to build a business from the ground up. Named Blue Chair Bay Rum, this alcoholic beverage comes in a bright green bottle and is Kenny’s baby. From deciding the color of the wrapper to choosing the cork material, and even selecting the ingredients, Chesney is involved in every decision.

Own Line Of Rum

Injured During Concert

During a concert in South Carolina, Kenny got injured because of a stage equipment mishap. While singing his third song, his foot got caught between a lift and the stage, and he ended up being trapped for a whole thirty seconds. Once he freed himself, he got back to singing, but it was clear to see by his limping that he was injured. With overflowing adrenaline and not wanting to disappoint his fans, Kenny managed to keep his performance incredible, accident and all.

Injured During Concert

An Enormous Crew

When Kenny goes on tour, it’s a serious business that involves taking an enormous crew on the road with him. The convoy consists of eight busses and 17 semi-trucks packed with equipment. Feeling overwhelmed sometimes, Kenny has admitted, “You could only imagine what diesel fuel costs me as an overall expense for this year.” Although this may seem intense, it is the life Kenny loves and he is meticulous about every detail, including the color of the tour bus.

An Enormous Crew

Philanthropy

Being one of the richest country celebrities lets Kenny afford to give back to many non-profit organizations. He has been recognized for establishing the Spread The Love fund to pay for medical expenses of those affected by the Boston Marathon bombing. Aside from handing over checks of high numbers, he’s paid many visits to injured people in the hospital. Kenny gives fans opportunities to register to donate bone marrow at some of his concerts. The country star’s 2015 tour might have saved up to 25 lives thanks to stadium registration initiated by Kenny.

Philanthropy

His Mistress

Anyone who knows a thing about Kenny Chesney will tell you that he has immense passion and drive in everything he does. Even when achieving great heights, Kenny still feels the need to climb higher and always needs more. He says that he resembles a shark in that he always must be moving to stay alive. Writing songs has helped Kenny cope with the post-breakup sadness on several occasions and has brought forth some of his greatest works. Kenny claims to be content as a single man, with his mistress being his music.

His Mistress

Live-Stream Concert

It’s important for Kenny to create an intimate experience with his fans and he strives to reach as many people as possible during his concerts. To reach even more people, he streamed one of his New Jersey shows for the whole globe to see. With the help of the legendary director, Jonathan Demme, Chesney was able to bring the Jersey shore to the internet. Following Demme’s death, five years later, Kenny mentioned that he will always remember Jonathan’s ability to capture music on film in a way that kept the heart and energy intact.

Live-Stream Concert

Humility Of The Millionaire

Kenny is known to many as a down-to-earth and humble man. Rolling Stone magazine even noted once that he “wears his fame very lightly, if at all”. It’s true when they say Kenny feels most at home while sitting at a Virgin Island burger place. Not only in the burger joint, but also in the back alley of it, where the propane tanks and ice-makers are stored. Chesney claims this is his happy place – and an executive suite where he can come and relax.

Humility Of The Millionaire

Attractive… Tractor?

Country music is often made fun of for babbling too much about pickup trucks and snakeskin cowboy boots. Kenny, without doubt, encouraged this stereotype when he released his single, “She Thinks My Tractor’s Sexy.” The singer was aware that his song was a bit ridiculous and even said, “I was smart enough to record that song but I was smart enough also not to record another one.” Ironically, Kenny owns two tractors, but he doesn’t think of them as “sexy.”

Attractive… Tractor?

Current Girlfriend Mary Nolan

We haven’t heard too much about Kenny’s dating life, and this may be because of how his previous short marriage was ridiculed in the media. Avoiding discussing his romantic life with publicists, rumors spread once that Chesney was dating Miranda Lambert, but that turned out to be a folk tale. He did, however, bring along a gorgeous brunette date at the American Countdown Awards. Her name is Mary Nolan and we don’t know much about her, besides the fact that she is Kenny’s current lover.

Current Girlfriend Mary Nolan

Three Showers Per Day

On a typical day, you’d expect to catch Kenny doing one of three things: working out, relaxing on the beach, or performing on stage. Sounds like a great life, huh? Wrong! Kenny hates getting sticky and sweaty and avoids all activities that promote perspiration. Kenny has noted on several occasions that he’s a clean freak and takes three showers per day. He uses body wash (not soap – because it gives him the heeby-jeebies) to make sure he isn’t sticky and is always reapplying deodorant to avoid stinking.

Three Showers Per Day

Loves Free Spirits

Kenny hates objectifying women, and becaue of that, he wrote, “Wild Child,” which describes the personality of “his kind of girl.” In the song, Kenny sings about loving a free spirit that looks royal in a thrift store dress and keeps his heart and her hair a mess. These lyrics coincide with previous statements he’s made about looking for a lover who is smart, carefree, and hippy-ish. He also threw in that his ideal partner would be a big food-lover.

Loves Free Spirits

Turned Pop Star P!NK Country

Pink isn’t exactly the epitome of an Alabama farm girl and she sure is far from the dusty roads and cold beers of country music. Tastefully combining elements of pop, rap, and rock, Pink has collaborated with various-styled artists all over the globe. She’s worked side-by-side with Eminem, Naughty By Nature, and even Steven Tyler. Pink and Kenny released a song called “Setting The World On Fire” which was featured on Chesney’s album, Cosmic Hallelujah.

Turned Pop Star P!NK Country

$25 For Freebird

When Kenny was just a beginner guitar player, he didn’t have a long list of original songs to play, so instead, he played lots of covers. At the beginning of his career, he would perform in bars around his college campus and put a tip jar next to the stage. In order to avoid unwanted requests, he taped a sign to the jar, “tips welcome, but anything by James Taylor, Kimmy Buffet, or especially Free Bird is $25.” This wasn’t because Kenny didn’t love and respect the artists, but because he was sick of receiving the same requests all the time.

$25 For Freebird

Affair With Sara Evans?

Similar to Kenny, Sara Evans is a country singer and songwriter who loves what she does. Evans married Craig Schelske and had three children with him. The couple went through a nasty divorce years later, during which both accused each other of infidelity. The finger-pointing began when Sara first accused Craig of sleeping with the housekeeper. In court, Schelske fire back and accused his soon to be ex-wife of 11 affairs, one being with Chesney. Kenny responded to the accusation by calling them “ridiculous.”

Affair With Sara Evans?

College Is Important

Following high school graduation, Chesney enrolled at East Tennessee State Univesity and focused on studying advertising. College was a crucial part of Kenny’s maturing, as it forced him to grow up and take care of himself. He admitted that this was the first he realized no one could bail him out of life. Wanting to give back, Chesney offered to help ETSU raise money for a stadium. Six months after announcing his partnership with his alma mater, they were already 75 percent there to their $26.6 million goal.

College Is Important

No Shoes Nation

“No Shoes Nation” is the name of one of Kenny’s fan bases and it refers to his hit song, “No Shoes, No Shirt, No Problems.” The founders created a symbol for it too, which features a pirates flag with the classic skull and crossbones. During one of Chesney’s performances, he spotted a girl in the crowd, hairless from cancer treatment, and pulled her up on stage. When he sang to her, “every little thing is gonna be alright,” the crowd was speechless and in tears. No wonder Kenny’s fans are so dedicated.

No Shoes Nation

Three Weeks Of Playlists

Music is not something Kenny or anyone can produce with the snap of a finger. Lyrics need to be inspired and the mood must be perfect for a beautiful piece of music to come to life. It would take you about three weeks to get through every song in Chesney’s music collection, and that’s just if you listened on shuffle or straight through. Kenny’s music collection is sorted by playlist and he’s got one for every occasion. He even has a pre-show playlist which pumps him up and features songs by artists like AC/DC and Aerosmith.

Three Weeks Of Playlists

Made Two Documentaries

As we mentioned before, Kenny loves two things: sports and his home state, Tennessee. He combined these two passions by producing the documentary, The Color Orange. The film features Condredge Holloway, the star quarterback of the University of Tennessee. Condrege’s story is inspiring – he’s is the grandson of a former slave, who became the first African-American quarterback to start in the Southeastern Conference. In addition to this film, Chesney produced another football documentary, The Boys Of Fall, where he interviewed many of his athletic-heroes.

Made Two Documentaries

Four Month Marriage To Renée Zellweger

Chesney and Renee Zellweger’s union was so short-lived that the bride literally forgot parts of it, commenting, “It’s a pretty big thing to forget, isn’t it?” The two first met at a tsunami relief fundraiser and got hitched not long after. Unfortunately, they ended up annulling their marriage four months after tying the knot. Chesney commented, “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

In The Beginning…

Kenny’s road to success was a long and bumpy one, and in order to really grasp it, we’ll need to go back to March 26th, 1968, the day that the country legend came into this world. Born at St. Mary’s Medical Center in Knoxville, Tennessee, Kenny was the son of a hair stylist and elementary school teacher. He was raised on humble values and spent his childhood beside his beloved little sister, Jennifer Chandler. His seemingly ordinary upbringing ended up being the kickstart to a great journey to superstardom.

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In The Beginning…

College Years

In terms of education, Kenny was always an academic achiever and even more so, an extracurricular pro. During his teenage years, in the ’80s, Chesney was an avid lover of sports and played on his high school’s baseball and football teams. While studying in college for a degree in advertising, Kenny received a spectacular Christmas present that forever changed the course of his life, “The Terminor.” This was Chesney’s first guitar, which he immediately taught himself how to play.

chesney 1
College Years

First Try At Music

Chesney recorded his first demo album right before he graduated college. After practicing for countless hours and building himself a strong reputation at local bars, the aspiring artist managed to sell 1,000 copies of his first record. With the money he banked, Kenny was able to afford himself a new guitar, which he took everywhere with him. Soon after, he moved to Nashville to further his music career, and that’s where his next big break occurred.

First Try At Music

So Many Albums

Following developing himself a name in Nashville, Kenny Chesney continued to climb the country music ladder. His first major label album was In My Wildest Dreams, which came out in 1994. Before he knew it, Kenny managed to release 17 additional solo albums – must recently, 2018’s “Songs for the Saints.” In addition, Kenny has created a handful of  Greatest Hits albums and released two live albums – 2006’s “Live: Live Those Songs Again” and 2017’s, “Live In No Shoes Nation”

So Many Albums

Award Winner

Kenny’s country music reputation has skyrocketed so high that he has even attained the admiration and support of many award academies and critics. Exactly ten years after releasing his very first album, the southern star was awarded his first Grammy nomination for Best Country Collaboration With Vocal for “Hey Good Lookin.” Over the years, Chesney was nominated a further five times for various Grammy awards. His most recent achievement is Best Country Album for “Cosmic Hallelujah” at the 60th Annual Grammy Wards in 2007.

Award Winner

Crazy Net Worth

After millions of records sold, numerous sold-out tours and creating himself an epic name, Kenny has turned into one of the most popular and most compensated artists in his field. We weren’t really surprised when we discovered that Chesney holds one of the top net worths among country music stars. In 2015, Forbes estimated that Kenny’s annual income reached roughly $42 million – a number he once never even dreamed possible. As of 2018, his net worth stands at a staggering $225 million.

Crazy Net Worth

Buddies With Tim McGraw

Remembering Kenny and Tim McGraw’s wild horse fiasco is naturally the first thing we think of when we hear these two epic names, but there are actually many other things to remember about this country duo. For one, remember the time when the two embarked on a co-headlining tour together?  Brothers of the Sun Tour saw Chesney and McGraw join forces once again, touring 22 venues in over two dozen cities. The tour grossed $96 million in ticket sales and hosted over a million people at each show.

Buddies With Tim McGraw

Question About Orientation

When Chesney and Renee got divorced, they got an annulment which cited “fraud” as the legal reasoning for their separation. The claim wasn’t exactly precise, but among the choices, fraud seemed the least harmful. Following the two parting their separate ways, the media started suggesting that Kenny was gay. Renee released a statement claiming, “It was simply legal language… not a reflection of Kenny’s character.” Chesney amusingly replied to the rumors by saying, “I’ve got a long line of girls who could testify that I’m not gay.”

Question About Orientation

Chesney’s Tailgates

Kenny Chesney’s concerts are always held in big stadiums and often sell out. The pre-show tailgates are an exciting scene, which see thousands of fans getting pumped for the concert. Unfortunately, in 2016 at a Pittsburgh concert, the excitement went too far and as a result of an overly rowdy crowd and intoxication, 25 hospitalizations occurred along with several arrests. Similarly, at a 2013 concert, 73 people were arrested and 30 tons of trash were left behind in the parking lot. Although devastating, those close to him still stayed by his side for support…

Chesney’s Tailgates

Involved In A Kanye And 50 Cent Dispute

If you’re familiar with Kanye West and 50 Cent, you’ll know that these two huge hip-hop stars are always in a contest with one other. In 2007, the two rappers decided to hold a public competition to see whose newly released album would sell more. Taking a risk, 50 Cent vowed to retire if Kanye came out on top. Just as things were heated enough, Kenny got involved in the trash talk and announced that he was also releasing a new album that same day. Unfortunately, Chesney made it in third place, with Kanye in first.

Involved In A Kanye And 50 Cent Dispute