His first major hit was "Fall in Love," which reached the Country Top 10 in 1995. The follow-up, "All I Need to Know," also reached the Top 10, but follow-ups were not so successful. However, in 1996, he scored the top 5 hit, "Me and You," and returned again with "When I Close My Eyes" in early 1997. He hit number one for the first time with "She's Got It All" in August 1997; the song spent three weeks atop Billboard magazine's country singles chart. Other number one hits included "How Forever Feels" (six weeks in 1999); "The Good Stuff" (2002); "There Goes My Life" (2004); and "When the Sun Goes Down" (a duet with Uncle Kracker in 2004). Notable number twos include "That's Why I'm Here" (1998), "Young" (2002), "Big Star" (2003), "No Shoes, No Shirt, No Problem" (2003) and "The Woman With You" (2004). While some of Chesney's music shows the obvious influence of John Mellencamp and Jimmy Buffett (a point critics are quick to note), he often performs several traditional country songs at his shows (particularly, music from George Jones). He won the Country Music Association's Entertainer of the Year honor in 2004. In January 2005, Chesney released the album Be As You Are: Songs from an Old Blue Chair, supporting the album with his "Somewhere in the Sun" tour and in November 2005, Chesney released his second album of the year The Road And The Radio.

On May 9, 2005, Chesney married Renée Zellweger on the resort island St. John in the U.S. Virgin Islands. The pair met in January 2005 at a tsunami relief benefit. Chesney had previously commented that Zellweger was his favorite actress, and he had written a song, "You Had Me From Hello", based on her line from Jerry Maguire. On September 15, 2005, after only four months of marriage, they announced their plans for an annulment. Zellweger cited "fraud" as the reason in the related legal papers. Fueled by numerous internet reports, some have speculated that Zellweger discovered Chesney was actually gay. According to People Magazine, Chesney was upset and responded to these rumors by stating: "They've done nothing short of calling me gay and her a whore. None of those things are true. I'm pretty firm in my sexuality and my love for women." Their annulment was officially finalized in late December 2005, putting an end to speculation that the couple was planning to start over.