On June 30, 1993, Kenny Chesney signed his first record deal, with the newly opened country division of Capricorn Records. The musician had moved to Nashville after graduating from East Tennessee State University, and managed to land a songwriting deal with publisher Acuff-Rose in 1992.

In a 2007 interview with HitQuarters, Chesney's longtime publisher, Troy Tomlinson, recalled that his friend, a BMI employee named Clay Bradley, initially met (and was impressed by) the then-aspiring artist.

"Clay called me up and said, 'I met this kid today from East Tennessee. He's a good singer, a good songwriter and, more than anything, I think you're going to really like him as a person,'" Tomlinson said, adding that he then met with Chesney and heard him play five songs, including "The Tin Man."

"I thought that he painted great pictures in his lyrics, particularly for someone who had not been around the typical Music Row co-writes," Tomlinson added. "I thought that he sang very well too, but more than anything there was a kind of this 'I-will-do-it' look in his eyes. I was really drawn in by the fact that he was so set on being successful in this business."

Chesney seized the opportunities the deals afforded him, and continued honing his craft. “That’s when my life started in this town," he told CMT in 2011. “All of a sudden, I wasn’t outside. I was writing with some of the best writers in the world."

In 1993, his performance at a songwriters showcase caught the attention of Capricorn Records, whose notable artists at the time included rock-leaning acts 311 and Widespread Panic. Chesney decided to sign with the nascent label.

Unfortunately, things didn't go quite as planned: "The people at Capricorn were wonderful, and they worked very hard for me," Chesney told Billboard in 1995. "The problem was that they weren't as well-networked or tuned into the country side of things as a major country label.

"Capricorn was a great experience for me, but I didn't know that they didn't have a regional staff to promote country records," he added. "I really didn't know what that was about. I was 23 years old, and they were offering me a record deal."

Unfortunately, the lack of staff — coupled with some reluctance at radio to support what they perceived as an unprepared label — sunk Chesney's debut album, 1994's In My Wildest Dreams. The album sold only 31,000 copies; to add insult to injury, Capricorn's country division then shuttered, leaving him label-less.

Of course, he wasn't down for long: In 1995, Chesney had signed to BNA Records and issued All I Need to Know, which spawned two Top 10 country chart hits.

WATCH: You Think You Know Kenny Chesney?

LOOK: Kenny Chesney Through the Years

More From TheBoot