During his high school years, Chesney aspired to become an athlete but ultimately pursued a different path. He went on to study at East Tennessee State University, where he earned a degree in advertising in 1990. It was during his freshman year that his mother gave him a guitar as a Christmas gift—an event that sparked his interest in music. He soon began performing at local clubs and restaurants in the Johnson City area near his college.

Early Music Career and Move to Nashville

In 1989, Chesney recorded and self-released his first album, selling approximately 1,000 copies. Following his graduation, he moved to Nashville to pursue a career in music. He began performing at The Turf, a well-known bar on Lower Broadway. His early performances eventually led to a songwriting deal with Acuff-Rose Music in 1992.

This opportunity paved the way for a recording contract with Capricorn Records. Under the label, he released his debut studio album, In My Wildest Dreams, in 1994. Though promotion was limited, the album sold over 10,000 copies. When Capricorn subsequently shut down its country division, Chesney signed with BNA Records, marking a significant step forward in his career. His second studio album, All I Need to Know, released in 1995, featured two Top 10 hits and elevated his profile in country music.

Breakthrough with BNA Records

Chesney continued building his career with BNA, releasing Me and You in 1996. The album produced several successful singles and expanded his fan base. In 1997, he was named Top New Male Vocalist by the Academy of Country Music—a milestone that solidified his place in the industry. That same year, he released I Will Stand, further boosting his chart success.

His breakthrough came with the 1999 album Everywhere We Go, which included hit singles like “You Had Me from Hello,” “How Forever Feels,” and “What I Need to Do.” The album earned widespread acclaim and commercial success, making it one of his most iconic releases.