He was driving in his car one day, listening to the radio, and he heard Merle Haggard sing "That's The Way Love Goes." That Christmas, Chesney asked for a guitar. He began practicing up to seven hours a day and started writing his first songs. He joined a bluegrass band, which played the local club and fraternity party circuit. After his college graduation with a degree in advertising, he wasted no time in getting to Nashville.

Chesney performed at a local Nashville club, but concentrated primarily on songwriting. His composing skills paid off when he was signed to a music publishing contract with Acuff-Rose Music. A recording contract with Capricorn Records followed soon after. His debut album with Capricorn was 1994's In My Wildest Dreams. The LP resulted in disappointing sales, thanks largely to Capricorn's almost concurrent decision to close their country division. Chesney moved to BNA Records and found the thrill of success with the 1995 release, All I Need to Know.

His second release, Me & You, resulted in Chesney's first No. 1 hit single, "When I Close My Eyes." The album went on to achieve gold certification. The LP was followed by I Will Stand, which contained two separate No. 1 hit singles. In 1999, he released Everywhere We Go, with the record-breaking single, "How Forever Feels," which stayed at No. 1 for a full six weeks. Everywhere We Go also achieved gold status before the end of the year.

Chesney was busy in 2000, as he toured and released Greatest Hits. The album would hit the No. 1 spot on the country charts. The hits package featured 12 of his biggest hits and five new songs.