Griggs' debut album, "You Won't Ever Be Lonely", was issued in 1999 via RCA Records Nashville. Certified gold by the RIAA, the album accounted for five singles on the "Billboard" country singles charts. The first three singles — the title track, "I'll Go Crazy" and "She's More" — were all Top Ten hits, peaking at number 2, number 10 and number 2 respectively. "You Won't Ever Be Lonely" also had the sixth-longest chart run on the country charts in the 1990s decade, spending thirty-six weeks on the charts. Following "She's More" was a non-album song, "Grow Young With Me", recorded as a duet with Coley McCabe, and after that, "Waitin' on Sundown" at number 50 and "You Made Me That Way" at number 19. Also included on the album was a duet with Griggs' idol Waylon Jennings in the track "Shine On Me", as well as a cover of Jennings' "Ain't Livin' Long Like This".