In 1995, he was signed to Epic Records,^[2] and his debut album, What I Live to Do, was released in 1996 under the production of Doug Johnson. The first single, "Dog on a Toolbox," peaked at number 64 on the Hot Country Songs charts, having been withdrawn as a single because label staff thought that there were too many songs about dogs at the time.^[6] After this song was withdrawn, its original b-side, "She's Got a Mind of Her Own" was shipped as the second single.^[7] This song peaked at 26 on the country music charts, followed by the number 2 hit "I Don't Think I Will" and the number 27 "All I Do Is Love Her."^[7] At the 1997 Academy of Country Music Awards, Bonamy was nominated as Top New Male Vocalist,^[6] and TNN Music City News nominated him as Star of Tomorrow.^[2] In addition, he toured in 1997 with Emilio Navaira, Clay Walker and Terri Clark.^[6]

Dan Kuchar of Country Standard Time gave the album a mixed review, praising Bonamy's voice but criticizing the songwriting on most of the tracks and saying that the album did not have a distinctive sound.^[8]

A second album, Roots and Wings, followed in 1997.^[9] Its lead-off single "The Swing" was his last top 40 hit at number 31; the other two singles were "Naked to the Pain" and "Little Blue Dot", reaching numbers 65 and 63 respectively.^[7] Bonamy wrote the track "I Knew I'd Need My Heart Someday" with Johnson and Pat Bunch, and chose the title track (which was written by Skip Ewing and Bill Anderson and previously recorded by Doug Supernaw^[6]) at the suggestion of Epic's A&R director, Debbie Zavitson.^[6]

อัลบั้มนี้ยังได้รับการวิจารณ์แบบผสมผสานจากCountry Standard Timeโดย Larry Stevens ชื่นชมเพลง "Daddy Never Had a Chance in Hell" แต่ติเพลงที่เหลือในอัลบั้มว่ามีเสียงที่เน้นป๊อปมากกว่า^{[ 10 ]} Thom Owens จากAllmusicให้คะแนนสามดาวจากห้าดาว โดยกล่าวว่าเขาคิดว่าอัลบั้มนี้ดีขึ้นกว่าอัลบั้มแรก^{[ 11 ]}