Nothing screams America quite like a Kenny Chesney's song. Throughout his career, the country music superstar has released over 40 top 10 singles, collected multiple Country awards, and performed in sold-out venues all over the country. So, why can't Chesney find the woman of his dreams and finally settle down?

While there's no shortage of suitors for the bald, cowboy-wearing Country star, Chesney's bachelor reputation remains unchanged after 32 years of professional songwriting and 52 birthdays without a wedding ring on his finger. Still, he has a fascinating romantic life to his name. So, let's get to know more about the man and the lover behind the Kenny Chesney myth!

Married To The Crowd

In Kenny Chesney's crazy life, only one thing has remained unchanged: his chemistry with the crowd. The Country music superstar isn't a settle-down kind of man, but he seems faithfully committed to his fans. He's a hardworking singer, songwriter, and record producer, with a big list of hits to his name.

But wait, wasn't Chesney married to a certain famous actress at one point? Well, technically yes, but that didn't go very well, as we'll show you in a moment. Chesney is an eternal Country music bachelor, whose sole inseparable friend is his guitar.

Kenny & Renée

So, now you remember? Back in 2004, Chesney got a chance to meet the Texan-born actress Renée Zellweger while attending a tsunami relief event. The country idol and the rom-com superstar hit it off immediately, and the two would be walking down the aisle only a year after, in May 2005.

It seemed like a love story written in the clouds. But while Chesney and Zellweger looked stunning together, their private life was more nuanced. To say things between the two ended badly is an understatement. They split-up after just four months, with Zellweger filing for fraud.

Commitment Issues?

Kenny and Renée's divorce is still the topic of controversy today. While the two celebrities have done their best to keep it in the past, the news of a fraud accusation was too bombastic for the press to ignore. But after all, what happened to these two?

While there's still a lot we don't know about Kenny and Renée's high-profile split-up, one thing's for sure: Kenny wasn't at all prepared to live the life of a committed married man. Reportedly, Chesney has confessed that he didn't support every aspect and responsibility of married life, without specifying what he was referring to.

Admitting to Fraud

After counseling with his team of lawyers, Chesney ended up admitting to fraud regarding his marriage with Renée Zellweger. There are many opinions on this subject, and most are unfounded. Still, the general belief is that Zellweger was accusing Chesney of not abiding by all the clauses of the wedding contract.

Long story short, Kenny and Renée were officially separated after just four months. For the actress, it was a love-story gone array that she wanted to forget as soon as possible. But for Kenny, it was an eye-opening event that allowed him to learn a lot about himself.

Free Like a Bird

The Quetzal is a type of Neotropic bird that's said to die if jailed. Kenny Chesney, being a free-spirited man, is a lot like the Quetzal. The prolific songwriter loves to spend weeks at a time in his boat, where he does some of his best work. So maybe that's why he's not the marrying type.

In an interview with an adult magazine, Chesney confessed that he doesn't believe to be suited to live an ordinary life. Being 'ordinary' is never an issue when you're a high-profile Country superstar, but maybe he was referring to something deeper? Perhaps he was saying his heart could never belong to one single woman?

A Late Bloomer

It's not like Kenny's not suited for love or romance. Everybody is. He's simply the kind of man who likes to feel he's wholly free to commit to his music. But did you know that the bald Country hunk is a late bloomer when it comes to love?

It turns out the singer-songwriter only got his first intimate relationship back in college. It's odd, especially considering how much of a heart-melter Chesney is nowadays. But surprisingly, Chesney seems to have spent his high-school days doing more guitar strumming than skirt-chasing. It paid off in the end!

A Man Used to Hearing 'No'

Sometimes, it takes being a celebrity to live in a world without rejection. Today, few women would say 'no' to a man like Kenny Chesney, but it wasn't always like that. Back in the early days of his career, the Country superstar was just a guy with a guitar, and he got rejected by lots of girls.

One, in particular, made a significant impact on the singer, who decided to write a song about winning over a woman's heart after a rejection. Was this secret early passion of Chesney "the one that got away"? We cannot know for sure, since the song wasn't enough to change this mysterious woman's mind.

From Zero To 100

A late bloomer and a broken-hearted suitor, Chesney's romantic life changed for the best back when he first started topping the charts in the early 2000s. Making the most out of his newly-acquired fame, the singer decided to make-up for the lost time and got intimate with lots of women.

And we mean, lots and lots of women! In an interview, Chesney has confessed to having been with over 100 ladies, which is impressive by all standards. Reportedly, the hunky Country superstar used these experiences to get some inspiration and improve his love songs.

Rumors & Speculation

Despite being a self-confessed womanizer, Chesney was still forced to deal with lots of speculation regarding his split-up with Renée Zellweger. Namely, the latest rumor in the celebrity news: could it be that Chesney was an active member of the LGBTQ community?

Even though this makes no sense whatsoever, some fans felt it was the only possible explanation for the fraud accusation filed by Zellweger. Others said that the fraud accusation was because of a mistress, which is a little bit more credible. But in the end, it seemed like there was only one explanation for Chesney's divorce.

In Bed... With His Songs

If there was ever a mistress in Chesney's life, music is that mistress. When you work as hard and diligently as Chesney does, it can be tough to prioritize anything else, even a relationship. Sorry girls, but the man is married to his guitar, and he's not going anywhere!

Maybe Zellweger was expecting a little bit more of cuddling and a little bit less of not seeing Kenny because he's writing songs on his boat. Either way, it seems like Chesney is only a fraud because he lives to fulfill his creative spirit and release quality records every other year.

His Dream Wife Lives Through His Music

It takes lots of dreaming to become a successful musician. It's not easy to consistently release songs that echo with the crowd and make listeners feel something. But Kenny is exceptionally skilled at writing relatable love songs with catchy melodies and heartfelt lyrics.

And his dream wife lives through some of his best love songs. In an interview, the Country idol described some of the personality traits of his ideal woman: she's not overly concerned about her appearance, she is carefree and easygoing, and she loves to eat. It seems like he's not asking for much!

To Love After a 'Fraud'

Chesney's dream woman seems to fit in the hippie, nature-loving category. But the woman that won the musician's heart after his high-profile divorce couldn't be any more different. For a start, she was a former Miss USA contestant, which means she probably paid a lot of attention to the way she looked.

But that's love for you; you never know when it's going to hit you. Chesney's post-divorce girlfriend was Amy Colley, a former Miss Tennessee that was working as a burn victim nurse back when she met Chesney. The two fell rapidly for one another and were later spotted vacationing together in the Bahamas.

Some Big Signs Of Love

Kenny and the gorgeous Amy Colley made for a beautiful and loving couple. But how serious was their relationship? Judging by the signs, pretty serious. The lovebirds were not only attending the Thanksgiving celebration of each other's families, but Colley was also permitted to drive Chesney's beloved truck.

This may seem like nothing, but if you're familiar with Chesney's songs, you probably know how much his truck means to him. The man released a hit-single about how hunky his tractor was, so yeah, vehicles do play a significant role in his life! And Colley was granted access to all things Chesney deemed important.

Stardom Gets In The Way

After two years of dating, it seemed as though Colley was the one for Chesney. But eventually, the crazy life of the Country superstar got in the way. As Chesney became even richer and more famous, his relationship with the former Miss Tennessee got more and more complicated.

Naturally, it doesn't help that Chesney spends most of his life touring the country, which is not something you can easily reconcile with a steady and committed relationship. Eventually, Chesney and Colley parted ways, and the Country hunk was rapidly seen enjoying the fortuitous company of other women.

Caught With Jenn Brown

Reportedly, Amy Colley decided to end things with Chesney after he was caught in the company of another woman. The former beauty queen was devastated as she saw her boyfriend spending some quality time with another gorgeous lady: the American sportscaster Jenn Brown.

You may know her from shows such as America Ninja Warrior and College GameDay, or perhaps for her stunning girl-next-door looks and beautiful blonde hair. The lovely Jenn proved to be irresistible for a hunk like Chesney, but their affair was sadly short-lasting. Don't worry, though, Chesney didn't waste any time before moving on.

Unconfirmed Romance

You know how these things go. When two celebrities start spending time together, the celebrity news will not miss the opportunity to call for a hook-up. And as Chesney grew friendlier and friendlier with the recently-divorced Country singer Sara Evans, rumors of an affair started appearing all over.

When questioned about his reported relationship with fellow musician Evans, Chesney said all allegations of romance were "ridiculous." So it seems like Kenny and Sara were never a couple. And in 2008, Evans re-married, this time with Jay Barker, a radio show host/former American football athlete.

Can't Get Enough of the Misses?

That's what being a celebrity bachelor will get you: a lifetime of rumors and speculation. A particularly preposterous one featured Jamie Hill, a former Miss Carolina beauty pageant contestant. According to some sources, Chesney and Hill enjoyed a secret relationship for as long as a decade! But does it make any sense?

The celebrity press was desperate to find out the lady making Chesney's heart beat faster. But they never thought that Chesney was possibly enjoying his solitude and writing songs in his boat. So, is there any truth to his reported 10-years hook-up with Hill?

And They Lived Happily Ever After...

In case you're wondering, that's Jamie Hill getting all smooshy with her husband. And, as you can tell by the man's gorgeous hair, that's not Kenny Chesney in the picture. It turns out Hill was already married with a lumberjack by the time she was being linked to the country singer-songwriter!

It's a case to say: don't believe everything you read on the Internet. But if Jamie Hill wasn't keeping Chesney busy, who was? As Hill got out of the picture, people started turning their attention to a lady that always seemed to be around Kenny.

More Than Fellow Musicians?

With a shared passion for Country music, Chesney and Texan singer-songwriter Miranda Lambert were extremely familiar with one another. They used to tour together, and they even appeared on the stage for some duets on one or two occasions. But could it be that Kenny and Miranda's relationship was more than a professional partnership?

There was no doubt the two musicians were friends. Kenny helped to launch Miranda's career by allowing her to open some of his shows. But were the two Country idols getting more than friendly remarks from one another?

Nothing But a Stage Act

After the Jamie Hill fiasco, the celebrity press sought redemption by linking Kenny and fellow musician Miranda Lambert. But once again, they got it completely wrong. Yes, Kenny and Miranda liked to show-off with some steamy duets, in which the chemistry between the two seemed way too real not to be. But it was all just a stage act.

Even though Kenny and Miranda can pull-off a highly-believable love duet, they're nothing but good friends. And according to Chesney, they've never been romantically involved. It's sad because they would make for an excellent Country music power-couple!

The Mysterious Mary Nolan

You can tell by now that anytime Chesney kisses a single woman in the cheek, the press goes crazy and sounds the love alarm. But there's one lady that was seen in the company of the singer who got closer than the rest: the mysterious Mary Nolan.

Not much is known about her, except that she attended the 2012 American Country Countdown Awards and spent some time on the backstage. Maybe this anonymous woman was showing her support for a certain famous boyfriend? It was possible. But first, it was essential to find out who Mary Nolan was.

Is She Kenny's New Bae?

There's more to Kenny and Mary Nolan's story than a kiss on the cheek. While a potential relationship between the two was never confirmed, Mary accompanied Kenny to a handful of award ceremonies, causing the media to speculate yet again.

Sure, you can take a friend to an award ceremony and, unless proven contrary, that's all there was to Kenny and Mary's relationship. But we wouldn't be surprised if the Country superstar and the gorgeous brunette were ever an item. Maybe due to all the pressure that was involved with his high-profile divorce with Renée Zellweger, Kenny has always chosen to keep his private life away from the spotlight.

The Man Behind The Star

With the rise of social media, it seems almost impossible that a high-profile figure such as Kenny Chesney has managed to keep his love life secret from the public. The singer-songwriter entertains full stadiums with his songs and has thousands of fans all over the U.S., but it's all still a mystery when it comes to the man behind the star.

This is particularly true about his love life. Other than his marriage with Renée Zellweger, Kenny has never publically announced who he was dating or for how long. He generally avoids the topic, even in his most intimate interviews.

A Trauma That Keeps Coming Back

Chesney may have chosen to keep his private life away from the public eye because of how badly the media explored his divorce from Renée Zellweger. In Kenny's pristine reputation, the legal accusation of "fraud" filed by his ex-wife is still the one scar that hurts the most.

And the scar would be open once again. When it seemed Kenny was recovered from all the media frenzy we've told you about, a bombastic interview with Renée Zellweger hit the shelves. And there were some whopping remarks about Kenny in there... Was the 'fraud' coming back to hunt the Country superstar?

Cover Story

It's one of those interviews that happen once or twice in a lifetime. At the height of her acting career, Renée Zellweger made the cover of the New York magazine with an intimate interview, conducted by the reputable Vogue editor/writer Jonathan Van Meter.

The interview focused mostly on Zellweger's new acting role and the impact the Hollywood show business industry had had on her. But the one line that made a sensation online was about... Kenny Chesney! It seems Zellweger, who's now 51 and recently divorced from musician Doyle Bramhall II, still has a couple of things to say about her mysteriously annulled marriage to Kenny...

What's She Up To Now?

Naturally, not even a celebrity of Zellweger's status happens to get a magazine cover without making some big headlines first. And back in 2019, the American actress was working on the role of a lifetime. She was selected to portray the legendary actress/singer Judy Garland in the movie Judy.

Garland was one of the main stars of Hollywood's Golden Age, and she's the kind of person every young actor wishes of one day portraying. Zellweger took her big shot with all she had, and the movie ended up receiving mostly positive reviews. But let's get back to Kenny Chesney and to that "bombastic" remark we've promised you...

Can It Be?

At one point during the New York interview with Renée Zellweger, writer Jonathan Van Meter mentions the fact that both Judy Garland and her daughter Liza Minnelli were married to men who were secretly involved with the LGBTQ community. And, according to Jonathan, Renée reacted very strangely to this reference.

When told about what happened to these two women, Renée simply made a funny face that seemed to indicate that this was a common situation for a lot of ladies out there. Possibly even Renée herself? Could it be that, just like Judy Garland and Liza Minnelli's former husbands, Kenny, too, was secretly involved with the LGBTQ community?

Readers Went Crazy!

To many people, Renée's cryptic expression during her New York interview was proof enough... The mysterious "fraud" accusations were solved once and for all! Kenny was not the womanizer many thought him to be, and Renée decided to annul the wedding after finding out her husband was, in fact, into men.

But wait, not so fast! We have to draw the line here. After all, a cryptic expression can mean anything, and it should never be enough to start making assumptions. Either way, there's nothing wrong with Kenny possibly being part of the LGBTQ community... It's just that he has never openly spoken about the subject before.

Renée & The LGBTQ

While Judy Garland is an icon of the LGBTQ community, Renée Zellweger is hardly involved in the matter. She rarely spoke about it, and she was never overly open about the subject. But going back to her New York interview, as well as some of her past remarks, she does have a strong opinion about it.

In search of clues that may help us to figure out whether Kenny is or isn't into men, it's essential to explore Renée's relationship with the LGBTQ community. After all, she got herself under the line of fire back when she decided to ignore the issue.

A Poorly-Timed Remark

Back when she was promoting the movie Judy in England, Renée was asked by a British magazine editor about what her personal opinion of the LGBTQ community was. In an answer she would later regret, Renée said something in the line of "I don't think much about it." Which is not what you want to hear from a woman who'd just portrayed one of the icons of the community!

Renée's answer was nothing but an innocent mistake. She has later explained she meant the exact opposite. But it was at least good for one thing: to get her to spill the beans and possibly provide a further clue to the romantic preferences of her former husband, Kenny Chesney!

Renée Explains

Going back to her seemingly uninterested statement about the LGBTQ, Renée decided to enlighten her fans as to what her real opinion on the subject was. She started by saying that she wasn't directly involved with anybody from the community, as she's not the mother, daughter, or sister of any LGBTQ member.

But she added by saying that she knew lots of people that were active members of the community. And, interestingly enough, she started listing them. It was then she mentioned a neighbor, a boss, a collaborator, a mentor, a student, a client, a partner, a customer, a best friend, and... an ex-boyfriend?

What About Now?

When Renée said she was the ex-girlfriend of a member of the LGBTQ community, it was as though she had mentioned Kenny Chesney by name. To many already-suspicious fans, this was all they needed to conclude: so that's what the famous "fraud" was all about!

But, once again, let's make an effort not to get ourselves ahead of the facts. After all, Renée has many ex-boyfriends to her name, with Kenny being just one of them. There's a big chance the closeted LGBTQ ex-boyfriend Renée was referring to is not Kenny, but a different major celebrity instead. But who could it be?

The Mystery Remains Unsolved

Sadly, the "fraud" mystery remains unsolved, with Renée choosing not to give a definitive answer on the subject. Maybe we'll have to wait for her next big interview? But right now, all we know is that Renée was involved with a member of the LGBTQ community, which means there's a good chance some big Hollywood stars have a hidden taste for men.

Renée's dating history features some big names, with Kenny Chesney being just one of the celebrities on the list. She also dated actor Luke Perry, web entrepreneur Dan Abrams, millionaire André Balazs, musician Jack White, and comedian/actor Jim Carrey. Additionally, she was reportedly involved with the likes of George Clooney and John Krasinski.

Songs of Truth

Since Renée isn't prepared to openly speak about her annulled wedding with Kenny Chesney, it's probably time we look for answers in the musical portfolio of the country superstar. After all, if there's a place where truth can be found, that's in the work of a dedicated artist like Chesney.

And his beautiful song "You Save Me" seems to be all about his short-lived but passionate marriage to Renée Zellweger. One particular line of the song seems to show just how much Chesney was into Renée: "It's hard lovin' a man, that's got a Gypsy soul," to which is later added, "You're the angel that believes in me, like nobody else / And I thank God you do." Sounds like true love, don't you think?

Chesney's Lone Spirit

"You Save Me" is a beautiful Kenny Chesney love song about what happens when a woman is genuinely in love with a man. But his tune "Better as a Memory" is perhaps an even more passionate description of Chesney's feelings. Particularly when you consider how much of a loner the Country composer is.

Lines such as "I'm built to fade like your favorite song" and "I'm better as a memory than as your man" seem to describe Chesney's restless personality to perfection. And, a secret member of the LGBTQ community or not, one thing's for sure about the American singer: he has a big heart and a big talent for putting it into words.

A Baseball Jock From Tennessee

Given how gifted Kenny is for playing the guitar and writing great songs, you would think of him as a shy and artistic kid. But while growing up in Knoxville, Tennessee, Chesney was more into sports than he was into music. Before learning how to play the guitar by the time he was 18, he played football and baseball at his school.

He lived happily with his parents - a hairdresser and a school teacher - and his sister Jennifer. His first guitar, which he received for Christmas, was called "The Terminator." Throughout his entire adult life, the guitar would become Kenny's most reliable and constant companion.

The College Days

Interestingly enough, Kenny's college days were also not directly linked to his music career. Instead of pursuing an art course, he decided to attend advertisement classes at Johnson City's East Tennessee State University. But, as you can tell by the picture, he already rocked a cowboy hat in true Country-music style!

Away from the classes, Kenny was working on his plan B: his music. And it wasn't too long before plan B became plan A. With a couple of songs written to his name, Chesney was prepared to take the local music scene by storm and start climbing the ladder to success.

The First Demo & The First Applauses

Back in 1989, a young and ambitious Kenny Chesney recorded his first demo tape. It was, as all demos are, a humble and limited edition. But Kenny was able to sell a reported 1,000 copies in Johnson City alone! It was a remarkable feat, especially considering it was only a demo.

When your first attempt at music goes this well, you know you're on the right path. And Kenny knew right away music was his destiny. He started performing periodically in the area, making several shows at Nashville's The Bluebird Cafe and becoming a resident at a bar called The Turf.

Getting Serious About It

Kenny Chesney's residence at The Turf wouldn't be possible if it weren't for his decision to move to a bigger city. Nashville is the center of America's Country music scene, which meant Chesney was at best possible place to pursue a musical career.

His years in Nashville were vital for his later success. Not only because the city provided him with the opportunities he needed, but also because he was learning daily about how to deal with the crowd and how to write better songs. If there's a place where stars are made, that's Nashville. And moving to the big city was likely the best decision Chesney'd ever made.

The Big Break

It took Chesney two years of living in Nashville to land his big break finally. It happened in 1992, back when the future Country superstar was able to get a meeting with Troy Tomlinson, an employee of the Opryland Music Group. Chesney was recommended to Tomlinson by Clay Bradley, a BMI executive who was impressed by Chesney's talent.

In his recommendation, Bradley wrote, "He's a good singer, a good songwriter, and more than anything, I think you're going to like him as a person." And he was right. When Tomlinson finally met Chesney, he couldn't be more pleased with his talent and determination!

A Recording Artist, Finally

After getting involved with the likes of Bradley and Tomlinson, Kenny Chesney was finally playing the big boy's game. And one year later, in 1993, he achieved his dream of officially becoming a recording artist. He signed a contract with the now-defunct Capricorn Records, which was then starting a new Country sub-division.

Even though Capricorn was an independent label, it could still provide Chesney with some tremendous opportunities. The name, which was active since 1969, was looking for a fresh face to lead their newly-established country section, and Chesney was as good of a choice as they could've ever made.

The First Attempt Isn't Always The Brightest

Today, there's no question Capricorn made a good decision by signing Kenny Chesney. The man is a country legend! But back in 1994, Chesney's very first album, In My Wildest Dreams, didn't do as well as expected. Selling 10,000 copies sounds like a lot, and it surely was an improvement for Kenny, but it wasn't exactly a breakthrough.

Shortly after, Capricorn decided to close their country sub-division, leaving Chesney without label once again. It was a sour outcome for Chesney's dreams of succeeding at Capricorn, but, when looking at the bigger picture, it was nothing but a hick-up in the singer's path to success.

Topping the Charts

In the end, Chesney's exit from Capricorn was probably a good thing. Kenny signed with BNA, a larger country label that was backed by the gigantic Sony. And this time, he was making sure a lot more people were going to buy and listen to his record.

Chesney's second album, titled All I Need to Know, did a lot better than his first attempt. With three songs making it to Billboard's top 40 (in the Country category), Chesney's name was finally getting general acknowledgment. "Who is this young rising star?" country fans all over the U.S. asked. Well, in less than two years, everybody would know all about Chesney.

It's a Number 1 Hit!

After paving the way with two increasingly successful albums, Chesney was ready for the big one. Between 1996 and 1997, the country singer released two of his best records: Me and You, and I Will Stand. Me and You became Chesney's first Gold album and granted him his very first award - the 1997 Academy of Country Music's New Male Vocalist of the Year distinction.

As for I Will Stand, it featured "She's Got it All," which was Chesney's first song to reach number 1 in the Country Billboard Chart. If there's a time a musician knows he's made it, that's when he gets that much-wanted number 1. And Chesney had finally done it!

Country Stardom

By the time No Shoes, No Shirt, No Problems came out in 2002, Kenny Chesney was a big name in the country music scene. The hit-song "The Good Stuff," featured on the record, spent seven weeks at number 1. By the year's end, "The Good Stuff" was U.S.'s number 1 country song for 2002.

With the album's success, Chesney was granted several awards, including ACM's Top Male Vocalist of the Year. But most importantly, he showed everyone he wasn't going anywhere. After getting to the top of the country music scene, Chesney was determined not to leave. The days of recording demos and performing at local bars couldn't feel any more distant by now.

The Good Stuff

Out of Chesney's irreprehensible catalog of love songs, "The Good Stuff" is a definite standout. The song made Chesney lots of money, but its content seems to be all about what's most important in a person's life. It tells the story of a man who goes to a bar after having a big fight with his lady.

In the bar, he meets a widower bartender, who tells him about the things that matter the most: love, family, and spending time with the ones you cherish. If you love country music for the stories, you need to check out "The Good Stuff." It's a simple but very compelling song, in true Kenny Chesney style.

Number 1 Album? Here You Go!

After releasing a Christmas album, Kenny went on to produce the acclaimed When the Sun Goes Down. The record came out in 2004, and it was the first album from Chesney to peak at number 1. The single "There Goes My Life" spent seven weeks on the top of the charts, while  "I Go Back" received the Country Music Television's Male Video of the Year Award.

Playing for fully-packed stadiums and with even more awards to his name, Chesney went on to become a bonafide music star, getting widespread recognition even outside the country music niche. And once again, it was Chesney's unique ability to tell a compassionate story that got his music selling millions.

The Beautiful "There Goes My Life"

Even though Chesney is, by all means, a solitaire, he does have the talent to write convincing songs about family and taking care of others. "There Goes My Life," which was yet another hit for the Knoxville singer, tells the story of a man and his daughter from the moment she was born to the moment she leaves home.

It's certainly a relatable tune for every parent out there, and young parents in particular. With lines such as "So much for ditching this town and hanging out on the coast / Oh well, those plans are long gone" and "Momma's waiting to tuck her in / As she stumbles up those stairs," "There Goes My Life" is a certified tearjerker.

A Lone Wolf

While "There Goes My Life" seems to dwell in the most emotional details of family life, Kenny Chesney himself has already said that he doesn't plan to have kids. It looks like the country superstar would rather sing about family than build a family of his own.

And that's okay. Like most artists, Chesney was gifted with a brilliant but solitaire spirit. If a long-term relationship is already hard to keep for the songwriter, who loves to spend weeks at a time alone in his boat, a child is an even more significant threat to the freedom he so diligently tries to preserve. Romance aside, it's always going to be Kenny and his guitar.

Awards, Awards, Awards

Hollywood has the Oscars, music has the Grammys, and the country scene has the ACM awards. And when it comes to filling up his home with ACM gold, Chesney is a veteran pro. After receiving his first award in 1997, Kenny went on to strike gold in about every category presented by the ACM.

2004 was a big year, with Chesney receiving the distinction for Album of the Year and Entertainer of the Year. One year later, the bald hunk received the prestigious Triple-Crown Award, as well as a second distinction for Entertainer of the Year. Since then, he has never stopped winning awards and topping the charts.

A Resilient Fighter

You know he has the talent, the dedication, and the "it" factor. But Kenny Chesney is also a fighter who's ready to pay a high price to please his fans. Back in 2008, during the Poets and Pirates Tour, Chesney showed all of his grit by performing for about half-an-hour with several broken bones on his foot.

He got his foot stuck on a hydraulic lift, which was used to carry him into the stage, and he worked through the pain to present his fans with a memorable live performance. After checking his foot in the show's intermission, he realized the seriousness of the injury, but he continued touring nonetheless.

A Sports Fan With The Work to Show For It

Whenever he's not touring or writing songs, Chesney is probably watching some sports back home. A big fan of the American and Canadian football leagues, Chesney has taken his love for sports to a whole another level by producing and narrating a biographical movie about Conredge Holloway.

Holloway is a former NFL superstar from the '70s, who became the first African-American quarterback to achieve widespread recognition. The movie aired on ESPN in 2011, and it wouldn't have been possible if it wasn't for Chesney's admiration for the former athlete. Holloway is now 66 years old and was inducted into the Canadian Football Hall of Fame back in 1999.

Will He Ever Stop?

While some musicians like to relax after getting to the top, Kenny Chesney is showing no signs of slowing down, regardless of his impressive sales numbers and numerous accolades. Since 1994, he never takes more than two years before putting out some new material.

Between 2016 and 2020, he has recorded and released four new original albums, including the still-fresh Here and Now. He has also released the highly-influential No Shoes Nation, back in 2017. The album's title was later applied to the fanbase of the musician, with the words "no shoes nation," representing the love for a carefree lifestyle that's so vividly expressed through Chesney's life and work.

Here and Now

It's not possible to tell the full story of Kenny Chesney right away because it is still going on. At 52-year-old, the reputable country singer still has a lot to give to his fans, and it seems like his creative spirit is showing no signs of deteriorating. And he's still writing some great songs today!

"Here and Now" is the title track of its latest album, and it's a beauty. With lines such as "Ain't no better place, ain't no better time than / Here and now" and "Better get to living, 'cause all we've got is / Here and now," the song focuses on the most positive aspects of life.

Stage Animal

Kenny Chesney's life is all about going from 0 to 100. For a man who loves to spend time alone on his boat, working on new songs, Chesney finds it oddly comforting to play in front of thousands of people every other week. He's a restless live performer, with lots of successful tours to his name.

All that hard work pays off. Besides being granted several awards for his live performances, Chesney's stadium-size gigs have made him a wealthy man. In 2015, Forbes magazine estimated that Chesney's annual income was $42 million! But what is Kenny doing with all that money?

Giving Back to Others

For a loner, Chesney does have a kind heart. His philanthropic work is impressive, and Chesney played a crucial role in helping the population of the British Virgin Islands after the passing of Hurricane Irma back in 2017. Chesney owns a mansion in the islands, which ended up being used as a safe house by many of the locals.

After the tragedy, Chesney decided to pay further assistance to the afflicted. He founded the Love for Love City Foundation to help the victims of the disaster. Additionally, he donated all proceeds from his 2017 album Songs for the Saints to the same cause.

Collaborations & Crazy Adventures

Beloved by his fans of the "No Shoes Nation," Chesney is also a favorite amongst other musicians and celebrities. During his live shows, he has received some unexpected guests, including country legend Kid Rock, Payton Manning, Dave Matthews, and even Taylor Swift. Most recently, he's collaborated with pop singer Pink.

He's also good friends with fellow singer Tim McGraw. Reportedly, Chesney and McGraw were arrested in 2000 after a scuffle with the New York City police, which involved the stealing of a police horse. This goes to show that even good guys like Chesney and McGraw can drink one too many beers once in a while.

Forever Alone At The Top?

It's an inspiring story. Kenny Chesney went from being an ambitious advertising student from Knoxville to become a country superstar. Idolized by hundreds of fans, he's been one of America's top musicians for the past two decades, and it seems like he's not going anywhere.

The only thing missing? Miss Kenny Chesney. The country superstar likes to be alone and isn't looking for "the one," but when it comes to love, one never knows. Chesney's written so many great songs about love and family; it only makes sense one day he gets to experience all the emotions he so convincingly sings about. Meanwhile, his success story will continue to live on.