Kenny Chesney is one of the most famous and successful country singers in the world. From hits such as “Don’t Blink” and “You Had Me From Hello” to 20 studio albums and sell-out tours worldwide, he has gained millions of fans around the globe and become one of the most familiar faces in the popular genre.

But it’s not just his music and talent that has had the world talking all these years—it’s the whispers about the behind-the-scenes drama in this talented singer’s life, most particularly around his romantic relationships.

Let’s take a look back at this singing superstar’s rise to fame and the secrets of his love life along the way.

A Star is Born

Kenny Chesney was born Kenneth Arnold Chesney on March 26, 1968, in the town of Knoxville, Tennessee to parents Karen Chandler and David Chesney. Karen was a hairstylist in the local area, and his father David Chesney, worked as a teacher in the elementary school.

Together with his younger sister Jennifer, the young Chesney showed from an early age that he had an unusual talent and charisma—but no one could have predicted just how much of a star he would become.

Team Player

You may think that someone as talented and successful as Kenny Chesney, would have always shown from a young age a great appreciation and aptitude for music. But the truth is, even though the young Chesney was clearly exhibiting star qualities, it actually wasn’t in music that these first came out.

In Chesney’s early years, he was a big sports fan, playing football and baseball in high school. It wasn’t until he was 18 years old that Chesney picked up a guitar for the first time—and it would change his life forever.

The College Years

Now that Kenny Chesney had finally found his true passion and talent in music, you might think that his career path would be clear and set out. But the truth was, even though he was so in love with music and writing songs, the young Chesney simply did not view it as a career choice.

Instead, he enrolled at East Tennessee State University in Johnson City, studying for a degree in advertising. However, he kept playing and writing music throughout his studies, and by the time he graduated, he knew for sure that his destiny lay in the world of music.

Finding His Way

Finally, now that he was done with his college education, it was time for Kenny Chesney to pursue his music career in earnest. Being an independent spirit and free thinker, the ambitious young Chesney decided to release the album himself.

He promoted the album on his own, selling it at local clubs where he was performing.

The record sold around 1,000 copies—not quite platinum level sales, but it was enough to make Chesney enough money to buy himself a new guitar.

Not only that, but it gave him his first taste of life as a musician—and he loved it.

Music City

As Chesney began to become somewhat of a local star in his area, Chesney knew that if he really wanted to make it big in the music industry, he needed to live in a place where big things were happening and there was more of a scene around him—that way, he could increase his chances of being spotted by a possible talent scout from a record label.

So, in 1990 he upped his stakes and moved to Nashville, Tennessee, known worldwide as “Music City”, the epicenter of the country music scene—and his adventures were about to truly begin.

City Slicker

As Chesney settled into his new life in Nashville, he knew that he had to get himself noticed playing as much live music as possible and making his mark on the industry scene.

As luck would have it, he landed a job at a rowdy downtown bar known as The Turf. Chesney began working there regularly, as the resident performer for its partying customers.

The talented singer knew that this would be his ticket to stardom—but he had no idea of the journey ahead.

Big Break

As Chesney had hoped, his regular performances at The Turf began to catch the attention of big names in the music biz, and eventually he found himself on the receiving end of a pretty exciting phone call.

Clay Bradley, from BMI, wanted to set up a meeting between Chesney and Troy Tomlinson, from Opryland.

Tomlinson immediately saw Chesney’s talent and potential, and signed him up for a songwriting contract.

Chesney was finally on his way—but he was in for a bumpy ride before making it big.

A Great Sign

Sure enough, Chesney’s growing exposure was about to land him a deal that would make him a real life singing star, and change his life forever in a moment.

This moment came when he attended a songwriting showcase for Capricorn Records, an independent record label that had recently expanded its remit into a country music division right there in Nashville.
Tomlinson immediately saw Chesney’s talent and potential, and signed him up for a songwriting contract.

Thanks to his incredible performance in the showcase, Capricorn signed him to their label—and Chesney was now an official recording artist.