Bobby's last show with the band was in December of 1999 at the Grand Ole Opry. His departure was due to health reasons at the time. He continued to write songs for Sawyer Brown and recorded three more albums with them (2000's "Cafe On the Corner," 2002's "Bootleg," and 2004's "Mission Temple Fireworks Stand") before deciding to retire from touring in 2004 to spend more time with his family and focus on other business interests.
Despite no longer touring with the band, Bobby continued to cowrite songs for Sawyer Brown on their next two albums, 2006's "Can You Hear Me Now" and 2010's "The Boys Are Back."